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1.
The synthesis of (2R)-2-methyl-4,5-dideoxy and (2R)-2-methyl-4-deoxy analogues of 6-phosphogluconate is described. The synthetic strategy relies on the Evans aldol reaction for the installation of the chiral centres in the 2- and 3-positions. The selective phosphorylation at the primary alcohol function of (2R,3S)-3,6-dihydroxy-2-methylhexanoic acid benzyl ester (5) and (2R,3S,5S)-3,5,6-trihydroxy-2-methylhexanoic acid benzyl ester (20) was achieved with dibenzyl phosphochloridate and dibenzyl phosphoiodinate respectively, working at low temperature. (2R,3S)-3-Hydroxy-2-methyl-6-phosphonoxyhexanoic acid (9) was obtained in 25% overall yield from 4-benzyloxybutanol and (2R,3S,5S)-3,5-dihydroxy-2-methyl-6-phosphonoxyhexanoic acid (28) in 10% overall yield from L-malic acid. 相似文献
2.
Hao G Qing-Hua Z Miao-Miao J Jin-Shan T Cheng-Du M Kui H Michio N Nai-Li W Xin-Sheng Y 《Magnetic resonance in chemistry : MRC》2008,46(12):1148-1152
A series of polyketide-originated metabolites (1-5) were isolated from a marine sponge-derived fungus Mycelia sterilia. Of these, 1-3 were new compounds. Their structures were elucidated by spectroscopic methods as (4R*, 5S*, 6S*, 8S*, 13R*)-1-(2,8-dihydroxy-1,2,6-trimethyl-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl)-3-methoxy-propan-1-one (1), 4,8-dihydroxy-7-(2-hydroxy-ethyl)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one (2) and 1-methyl-naphthalene-2,6-dicarboxylic acid (3). In 1, the proton-proton long-range coupling phenomenon claimed attention and was discussed. 相似文献
3.
Six new alkaloids, broussonetines W, X, M1, U1, J3, and J2 (1-6) were isolated from the branches of Broussonetia kazinoki SIEB. (Moraceae) as minor constituents. They were formulated as (2R,3R,4R,5R)-2-hydroxy-methyl-3,4-dihydroxy-5-17-(cyclohexy-2-on-1(6)-enyl)heptyllpyrrolidine (1), (2R,3S,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-17-(cyclohexy-2-on-1(6)-enyl)heptyl]pyrrolidine-4-O-beta-D-glucopyranoside (2), (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(9R)-9,13-dihydroxytridecyl]- pyrrolidine (3), (2S,3S,4S)-2-hydroxymethyl-3,4-dihydroxy-5-(10-oxo-13-hydroxytridecyl)-5- pyrroline (4), (2R)-2-[(IS,2S)-1,2-dihydroxy-8-1(2R,3R,4R,5R)-5-(2-hydroxymethyl-3,4-dihydroxy-1-acetylpyrrolidinyl)loctyl]piperidine (5), (2R)-2-[(1S,2S)-1,2-dihydroxy-8-[(2R,3R, 4R,5R)-5-(2-hydroxymethy]-3,4-dihydroxypyrrolidinyl)]octyl]piperidine (6). 相似文献
4.
Concellón JM Rivero IA Rodríguez-Solla H Concellón C España E García-Granda S Díaz MR 《The Journal of organic chemistry》2008,73(15):6048-6051
The transformation of enantiopure (2R,4R)- and (2S,4S)-N,N-dibenzyl-1,2:4,5-diepoxypentan-3-amine, 1 and 2, into the corresponding enantiopure (3S,5S)- and (3R,5R)-3,5-dihydroxy-3-aminopiperidines, 3 and 4 respectively, is described. The opening of the two epoxide rings with a range of amines takes place with total regioselectivity and high yields, in the presence of LiClO4. A mechanism to explain this transformation is proposed. 相似文献
5.
Five new alpha-tetralonyl glucosides, juglanosides A-E (1-5) were isolated from the fresh rejuvenated fruit of Juglans mandshurica. Their structures were elucidated as (4S)-4-hydroxy-alpha-tetralone 4-O-beta-D-glucopyranoside (1), (4S)-4,5-dihydroxy-alpha-tetralone 4-O-beta-D-glucopyranoside (2), (4S)-4,6-dihydroxy-alpha-tetralone 4-O-beta-D-glucopyranoside (3), (4S)-4,5,8-trihydroxy-alpha-tetralone 4-O-beta-D-glucopyranoside (4), and (4S)-4,5,8-trihydroxy-alpha-tetralone 5-O-beta-D-glucopyranoside (5) on the basis of spectroscopic analysis and chemical evidence. 相似文献
6.
不对称催化是由潜手性反应物合成光活性化合物的有效途径,α,β-不饱和氨基酸的氢化立体选择性已达90%以上,L-Dopa的工业化生产则标志着不对称催化氢化开始走向实际应用。高选择性的催化剂一般是一价铑的手性双膦配体络合物,其中DIOP[2,3-O-异丙叉- 相似文献
7.
Four new pyrrolidine alkaloids, broussonetines R, S, T, and V and a new pyrroline alkaloid, broussonetine U were isolated from the branches of Broussonetia kazinoki SIEB. (Moraceae) in low yield. Broussonetines R, S and T were formulated as (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(1R)-1-hydroxy-3-[6-(4-hydroxybutyl)-cyclohexy-2-on-1(6)-enyllpropyl] pyrrolidine (1), (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(1R,10S)-1,10,13-trihydroxytridecyl] pyrrolidine (2), (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(1R,5S)-1,5, 13-trihydroxy-10-oxo-tridecyl] pyrrolidine (3). And broussonetines U and V were proposed to be (2S,3S,4S)-2-hydroxymethyl-3, 4-dihydroxy-5-(9-oxo-13-hydroxytridecyl)-5-pyrroline (4), (2R,3S,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(E)-9-oxo-13-hydroxy-3-tridecenyl] pyrrolidine (5), respectively, by spectroscopic and chemical methods. 相似文献
8.
A convenient approach for the preparation of (2S,3R,4R,5S,6R)-2-(3-(4-ethylbenzyl)-4-chlorophenyl)-6-(hydroxymethyl)- tetrahydro-2H-pyran-3,4,5-triol I is developed. The target compound via four steps is synthesized from 4-bromo-2-(bromomethyl)- 1-chlorobenzene and the isomers of undesired ortho-products were avoided during the preparation. 相似文献
9.
A reaction of methyl (4R,5R)-4,5-epoxy-2(E)-hexenoate 1 with N-benzylmethylamine gave a diastereomerically pure methyl (4R,5R)-4,5-epoxy-(3S)-N-benzylmethylamino hexanoate 6 and methyl (4S,5R)-4-N-benzyl-methylamino-5-hydroxy-2(E)-hexenoate 7. The former was chemoenzymatically converted to (-)-osmundalactone 11, which is an aglycone of osmundalin. On the other hand, the directly conjugated addition of dimethylamine to methyl (4S,5S)-4,5-epoxy-2(E)-hexenoate 1 followed by treatment with MeOH at 40 degrees C exclusively provided methyl (4R,5S)-4-dimethylamino-5-hydroxy-2(E)-hexenoate 16, which was converted into L-(-)-forosamine 18. 相似文献
10.
Shibano M Tsukamoto D Fujimoto R Masui Y Sugimoto H Kusano G 《Chemical & pharmaceutical bulletin》2000,48(9):1281-1285
Four new pyrrolidine alkaloids, broussonetines M, O, P, and Q, were isolated from the branches of Broussonetia kazinoki SIEB, (Moraceae). Broussonetines M, O, P, and Q were formulated as (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(10S)-10,13-dihydroxy-tri decyl]pyrrolidine (1), (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(E)9-oxo-13-hydroxy-3- tridecenyl]pyrrolidine (2), (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(E)10-oxo-13-hydroxy-3-++ +tridecenyl]pyrrolidine (3), and (2R,3S,4R,5R)-2-hydroxymethyl-3-hydroxy-4-(beta-D-glucopyranosyloxy++ +)-5-[10-oxo-13-(beta-D-glucopyranosyloxy)tridecyl]pyrrolidine (4) respectively, by spectroscopic and chemical methods. 1-4 inhibited beta-glucosidase, beta-galactosidase and beta-mannosidase. 相似文献
11.
Ma G Li W Dou D Chang X Bai H Satou T Li J Sun D Kang T Nikaido T Koike K 《Chemical & pharmaceutical bulletin》2006,54(8):1229-1233
Five new monoterpene glycosides, rhodiolosides A-E (1-5), were isolated from the roots of Rhodiola rosea (Crassulaceae). Their structures were elucidated as (2E,6E,4R)-4,8-dihydroxy-3,7-dimethyl-2,6-octadienyl beta-D-glucopyranoside (1), (2E,4R)-4-hydroxy-3,7-dimethyl-2,6-octadienyl alpha-D-glucopyranosyl(1-->6)-beta-D-glucopyranoside (2), (2E,4R)-4-hydroxy-3,7-dimethyl-2,6-octadienyl beta-D-glucopyranosyl(1-->3)-beta-D-glucopyranoside (3), (2E,4R)-4,7-dihydroxy-3,7-dimethyl-2-octenyl beta-D-glucopyranoside (4), and (2E)-7-hydroxy-3,7-dimethyl-2-octenyl alpha-L-arabinopyranosyl(1-->6)-beta-D-glucopyranoside (5), on the basis of various spectroscopic analyses and chemical degradation. 相似文献
12.
Yanagi T Kitajima A Anzai K Kodama K Mizoguchi J Fujiwara H Sakiyama H Kamoda O Kamei C 《Chemical & pharmaceutical bulletin》1999,47(11):1650-1654
Of 4-amino-5-chloro-2-methoxy-N-(1-ethyl-2-hydroxymethyl-4- pyrrolidinyl)benzamide, four optical isomers, (2S,4S)-1 (TKS159), (2S,4R)-25, (2R,4S)-26 and (2R,4R)-27, were prepared from optically active 4-amino-1-ethyl-2-hydroxymethylpyrrolidine di-p-toluenesulfonate [(2S,4S)-14, (2S,4R)-17, (2R,4S)-20 and (2R,4R)-23, respectively]. The requisites, (2S,4S)-14, (2S,4R)-17, (2R,4S)-20 and (2R,4R)-23, were prepared from a commercially available trans-4-hydroxy-L-proline. The absolute configurations of (2S,4S)-1 (TKS159), (2S,4R)-25, (2R,4S)-26 and (2R,4R)-27 were spectroscopically determined. Of the benzamide derivatives, four optical isomers, (2S,4S)-1, (2S,4R)-25, (2R,4S)-26 and (2R,4R)-27, showed a relatively potent affinity for 5-hydroxytryptamine 4 (5-HT4) receptors in a radioligand binding assay ([3H]GR113808). The activities of 25-27 were less effective than that of 1 for the gastric emptying of a phenol red semisolid meal in rats. All this suggests that the most potent of the isomers was 4-amino-5-chloro-2-methoxy-N-[(2S,4S)-1-ethyl-2- hydroxymethyl-4-pyrrolidinyl]benzamide (1). 相似文献
13.
M. Madesclaire P. Coudert V. Gaumet V. P. Zaitsev Yu. V. Zaitseva 《Chemistry of Heterocyclic Compounds》2006,42(5):665-670
We have synthesized a series of (1R,2R,4S,5S,8S)-2,8-diaryl-4-(4-nitrophenyl)-1-aza-3,7-dioxabicyclo[3.3.0]octanes as a result
of reaction of (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediol with aromatic aldehydes. The structure of the compounds obtained
was established on the basis of 1H NMR data.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 757–763, May, 2006. 相似文献
14.
M. Vorona I. Potoročina G. Veinberg I. Shestakova I. Kanepe M. Petrova E. Liepinsh E. Lukevics 《Chemistry of Heterocyclic Compounds》2007,43(5):646-652
The reaction of tert-butyl 7α-chloro-and 7-β-chloro-7α-isopropoxy-3-methyl-1,1-dioxoceph-3-em-4-carboxylates with the Vilsmeier
reagent was carried out with introduction of N,N-dimethylaminomethylene group at position 2 in the E-and Z-isomeric forms.
Prolonged treatment of tert-butyl 7α-chloro-3-methyl-2-(N,N-dimethylaminomethylene)-1,1-dioxoceph-3-em-4-carboxylate with
hydroxylamine hydrochloride in acetonitrile at 40–50°C gave tert-butyl 10(S)-chloro-6-methyl-5-oxa-1,1,9-trioxo-1-thia-4,8-diazatricyclo[7,2,0,02,6]undecane-7(R)-carboxylate which isomerized into 1-tertbutoxycarbonylmethyl-3α-chloro-4-(5-methylisoxazole-4-sulfonyl)azetidin-2-one.
In the case of tertbutyl 7β-chloro-7α-isopropoxy-3-methyl-2-(N,N-dimethylaminomethylen)-1,1-dioxoceph-3-em-4-carboxylate the
analogous reaction gave tert-butyl 10β-chloro-(2S,6S,7S,10R,11R)-10α-isopropoxy-6-methyl-5-oxa-1,1,9-trioxo-1-thia-4,8-diazatricyclo[7,2,0,02,6]undecane-7(R)-carboxylate, the struc-ture of which was determined by 2D-NOESY two-dimensional spectroscopy. The compounds
synthesized showed weak or no cytotoxic activity with respect to monolayers of cancer cells in vitro. 相似文献
15.
The BF(3).Et(2)O-promoted Diels-Alder addition of 1-acetylvinyl RADO(Et)-ate (RADO(Et)-ate = 3-ethyl-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-exo-carboxylate) to 1-(dimethoxymethyl)-2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1]heptane led to one major monoadduct that added to 1,2-didehydrobenzene and was converted into (-)-4-demethoxy-7-deoxydaunomycinone and (2R)-12-acetoxy-2-acetyl-5-(bromomethyl)-1,2,3,4-tetrahydronaphthacen-2-yl RADO(Et)-ate. The latter compound was used to construct (8R)-8-acetyl-6,8-dihydroxy-11-[[(3'-[(aminopropyl)oxy]-, -4'-[(aminobutyl)oxy], and -5'-[(aminopentyl)oxy]methyl]-7,8,9,10-tetrahydronaphthacene-5,12-dione hydrochloride (-)-8, (-)-9, (-)-10, respectively, as well as (8R)-8-acetyl-6,8-dihydroxy-11- [[[2'-[(3"-aminopropyl)amino]ethyl]oxy]- ((-)-11) and -[[3'-[(3"-aminopropyl)amino]propyl]oxy]methyl]-7,8,9, 10-tetrahydronaphthacene-5,12-dione hydrochloride ((-)-12). (8R)-8-Acetyl-6,8-dihydroxy-11-[[(alpha-L-daunosaminyl)oxy]methyl]-7,8,9,10-tetrahydronaphthacene-5,12-dione hydrochloride ((-)-13), a mimic of idarubicin, was also prepared. Absorbance and fluorescence titration experiments showed (-)-8, (-)-9, and (-)-10 to intercalate calf thymus DNA whereas (-)-11, (-)-12, and (-)-13 did not. The best intercalator was (-)-9 (K(b) = (1.1 +/- 0.1) x 10(5) M(-)(1)) with the [(4'-aminobutyl)oxy]methyl chain. Inhibition of topoisomerase II-induced DNA strand religation was observed for (-)-8 at a concentration of 50 &mgr;M. 相似文献
16.
Mei Jin Shengbao Diao Changhao Zhang Shuo Cao Jinfeng Sun Ren Li 《Natural product research》2015,29(19):1839-1844
Two new diarylheptanoids, ( ? )-threo-3′,4″-epoxy-1-(4-hydroxyphenyl)-7-(3-methoxyphenyl)heptan-2,3-diol (1) and (1α,3β,5α,6α)-1,5-epoxy-3,6-dihydroxy-1,7-bis(3-methoxy-4-hydroxy-phenyl)-heptane (2), along with one known diarylheptanoid, rhoiptelol B (3), were isolated from the roots of Juglans mandshurica. The structures of compounds 1 and 2 were identified based on HR-ESI-MS, 1D and 2D NMR including 1H–1H COSY, HMQC, HMBC and NOESY spectroscopic methods. 相似文献
17.
报道了含1个溶剂DMF的多齿配体2,5-二羟基-1,4-苯醌缩氨基脲的合成和晶体结构。该化合物(C10N4O5H14)属正交晶系,其空间群为P212121 a=13.221(6),b=17.709(5),c=5.347(4)?, V=1252.0(1)3,Z=4,F(000)=568, Dx=1.434g/cm3,Mr=270.25, m (MoKα)= 1.16 cm-1, 结构由直接法解出,全矩阵最小二乘法修正,最终的偏离因子R=0.0319,wR=0.0748。结构测定表明溶剂DMF分子和2,5-二羟基-1,4苯醌缩氨基脲间形成很强的氢键,后者可看作是两条共轭链的偶合物。 相似文献
18.
A Ashimori T Uchida Y Ohtaki M Tanaka K Ohe C Fukaya M Watanabe M Kagitani K Yokoyama 《Chemical & pharmaceutical bulletin》1991,39(1):108-111
Optically active 2-[4-(4-benzhydryl-1-piperazinyl)phenyl]ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate [(S)-(+)-1 and (R)-(-)-1] hydrochlorides were synthesized with high optical purities from (R)-(-)- and (S)-(+)-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)- 3-pyridinecarboxylic acids [(R)-(-)-6 and (S)-(+)-6], which are available from (+/-)-6 by optical resolution using quinidine and cinchonidine, respectively. From pharmacological investigations of (S)-(+)-1 and (R)-(-)-1 such as the antihypertensive effect on spontaneously hypertensive rats and inhibition of [3H]nimodipine binding to rat cardiac membrane homogenate, the active form of 1 was defined to be the (4S)-(+)-enantiomer of 1. 相似文献
19.
Isaka K Nagatsu A Ondognii P Zevgeegiin O Gombosurengyin P Davgiin K Kojima K Ogihara Y 《Chemical & pharmaceutical bulletin》2001,49(9):1072-1076
Nine novel prenyl-dihydrofurocoumarin-type sesquiterpenoid derivatives, 2,3-dihydro-7-hydroxy-2R*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]-furo[3,2-c]coumarin, 2,3-dihydro-7-hydroxy-2S*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]-furo[3,2-c]coumarin, 2,3-dihydro-7-hydroxy-2S*,3R*-dimethyl-2-[4-methyl-5-(4-methyl-2-furyl)-3(E)-pentenyl]-furo[3,2-c]coumarin, 2,3-dihydro-7-hydroxy-2R*,3R*-dimethyl-2-[4-methyl-5- (4-methyl-2-furyl)-3(E)-pentenyl]-furo[3,2-c]coumarin, 2,3-dihydro-7-methoxy-2S*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]-furo[3,2-c]coumarin, 2,3-dihydro-7-methoxy-2R*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]-furo[3,2-c]coumarin, 2,3-dihydro-7-methoxy-2S*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]-furo-[3,2-c]coumarin, and 2,3-dihydro-7-methoxy-2S*,3R*-dimethyl-2-[4-methyl-5-(4-methyl-2-furyl)-3(E)-pentenyl]-furo[3,2-c]coumarin, were isolated from the roots of Ferula ferulaeoides [corrected]. The structures were established by comprehensive spectral analysis. The biosynthetic pathway leading to these prenyl-furocoumarin-type sesquiterpenoids is proposed based on their structures. 相似文献
20.
M. Madesclaire P. Coudert V. Goumet V. P. Zaitsev J. V. Zaitseva 《Chemistry of Heterocyclic Compounds》2006,42(6):813-817
The configuration of the asymmetric atoms in the molecule of (1R,2R,4S,5S,8S)-2,8-bis(4-chlorophenyl)-4-(4-nitrophenyl)-1-aza-3,7-dioxabicyclo[3,3,0]octane
has been determined using X-ray analysis.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 930-934, June, 2006. 相似文献