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1.
Stephen Hanessian Stéphane Marcotte Guobin Huang Olivier Loiseleur 《Tetrahedron》2006,62(22):5201-5214
The total synthesis of the bicyclic C-nucleoside malayamycin A is described starting with d-ribonolactone. A new method was developed to obtain preparatively important quantities of β-pseudouridine, which was used as an intermediate. The synthesis of a carba N-nucleoside analogue of malayamycin A is also described. 相似文献
2.
A practical and efficient synthesis of phosphatidylinositol pentam annoside (PIM5) was achieved based on a five-component one-pot sequential glycosylation protocol with exclusive regio- and stereo-selectivity. 相似文献
3.
Tetsuya Kajimoto Yuichi Ishioka Takahiro Katoh 《Journal of carbohydrate chemistry》2013,32(8-9):469-495
p‐Dodecylbenzenethiol (1) and p‐octyloxybenzenethiol (2) were synthesized as new odorless benzenethiols. Moreover, preparation of novel 1‐thioglycosides using 1 and 2 as well as their application for glycosylation reactions was performed. As a result, it was found that these 1‐thio‐glycosides were excellent glycosyl donors, and especially 2‐thio‐sialoside prepared from 1 and 2 afforded the best result to date in terms of α‐ and β‐selectivity in the sialylation where only the single C‐3 hydroxyl group of acceptor D‐galactopyranoside was free. All procedures from the preparation of thioglycosides to glycosylation reaction were attainable under completely odorless conditions. 相似文献
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5.
《Journal of carbohydrate chemistry》2013,32(4-6):415-424
An improved protocol for the large‐scale production of 1‐benzenesulfinyl piperidine and other sulfinamides is described. It is demonstrated that 1‐benzenesulfinyl pyrrolidine and N,N‐diethyl benzenesulfinamide function analogously to 1‐benzenesulfinyl piperidine in the trifluoromethanesulfonic anhydride‐mediated activation of thioglycosides, and that their less crystalline nature enables them to be used at ?78°C as opposed to the ?60°C required to keep 1‐benzenesulfinyl piperidine in solution. N,N-Dicyclohexyl benzenesulfinamide does not activate thioglycosides in combination with trifluoromethanesulfonic anhydride, which is attributed to its greater steric bulk. 相似文献
6.
The first synthesis of β‐L ‐glycoside 17 of the tetrasaccharide β‐Ant‐(1 → 3)‐α‐L ‐Rhap‐(1 → 3)‐α‐L ‐Rhap‐(1 → 2)‐L ‐Rhap is described (Schemes 1–3). Its spacer can be functionalized to make it amenable to conjugation to proteins by different conjugation methods. The synthesis was performed in a stepwise manner starting from the aglycon‐bearing terminal saccharide with thioglycosides as glycosyl donors. To attach the upstream terminal anthrose residue, the assembled linker‐equipped trisaccharide was glycosylated with ethyl 4‐azido‐3‐O‐benzyl‐2‐O‐(bromoacetyl)‐4,6‐dideoxy‐1‐thio‐β‐D ‐glucopyranoside ( 11 ). Further functionalization of the tetrasaccharide thus obtained, followed by deprotection gave the target substance 17 . Synthesis of substructures of 17 equipped with the same spacer, namely β‐L ‐Rhap‐1‐O‐(CH2)5COOMe ( 21 ), α‐L ‐Rhap‐(1 → 2)‐β‐L ‐Rhap‐1‐O‐(CH2)5COOMe ( 22 ), and α‐L ‐Rhap‐(1 → 3)‐α‐L ‐Rhap‐(1 → 2)‐β‐L ‐Rhap‐1‐O‐(CH2)5COOMe ( 23 ), is also described (Scheme 4). 相似文献
7.
Stereoselective synthesis of benzyl-protected β-galactosides by propionitrile-mediated glycosylation
Akiharu Ueki Masafumi Hirota Keiko Komatsu Yutaka Takano Michio Iwaoka Hironobu Hojo Yoshiaki Nakahara 《Tetrahedron》2008,64(11):2611-2618
β-Selective galactosylation was studied using a series of 2-O-benzylated phenyl 1-thio-galactosides and glycosyl acceptors in propionitrile with BSP-TTBP-Tf2O. The glycosylation enabled us to synthesize useful precursors of N-acetyllactosamine and core 1 O-glycoserine derivatives in a highly convergent manner. 相似文献
8.
Changning Wang 《Tetrahedron》2006,62(50):11657-11662
Gb3 and isoGb3 are both biologically important oligosaccharides. A new efficient synthesis of Gb3 and isoGb3 trisaccharide analogues has been achieved by one-pot sequential glycosylation strategy starting from simple monosaccharide building blocks promoted by N-(phenylthio)-?-caprolactam at room temperature. 相似文献
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Michel Weïwer Trevor Sherwood Robert J. Linhardt 《Journal of carbohydrate chemistry》2013,32(7):420-427
Floridoside (2-O-glycerol-α-D-galactopyranoside) is a natural glycerol glycoside found in red algae and is believed to play important roles in carbon storage, transport, and assimilation and in the regulation of osmotic balance. We describe here a rapid, high-yield, and high-stereoselectivity synthesis of floridoside in which the key step involves the 1,2-cis O-glycosylation of 1,3-dibenzylglycerol with ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside using iodonium dicollidine perchlorate (IDCP) or N-iodosuccinimide/trimethylsilyl triflate (NIS/TMSOTf) as promoters. 相似文献