Stereoselective 2-deoxy-β-O-glycoside synthesis based on remote activation of novel oxathiine donors

被引：0

作者：

Bartolozzi, A

Capozzi, G

Menichetti, S

Nativi, C

机构：

[1] Univ Florence, Dipartimento Chim Organ, CNR, Ctr Chim Composti Eterociclici, I-50121 Florence, Italy

[2] Univ Messina, Dipartimento Chim Organ & Biol, I-98166 Messina, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 2001卷 / 11期

关键词：

cycloadditions; deoxysugars; desulfurizations; glycosidations;

D O I：

10.1002/1099-0690(200106)2001:11<2083::AID-EJOC2083>3.0.CO;2-T

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stable glyco-fused 1,4-oxathiine derivatives, prepared by inverse electron-demand Diels-Alder reactions between suitable 1-glycals and 3-thioxopentane-2,4-dione, have been transformed into unusual glycosyl donors which, after "remote activation", react efficiently with glycosyl acceptors to afford 2-thio-beta -O-glycosides with total stereoselectivity. Several O-nucleophiles were successfully glycosylated. Reductive removal of sulfur transformed the 2-thio-beta -O-glycosides into the corresponding 2-deoxy-beta -O-glycosides without affecting the stereochemistry of the anomeric carbon atom.

引用

页码：2083 / 2090

页数：8

共 50 条

[21] Ligand-Controlled Stereoselective Synthesis of 2-Deoxy-β-C-glycosides by Cobalt Catalysis
Liu, Bingxue
Liu, Deguang
Rong, Xianle
Lu, Xi
Fu, Yao
Liu, Qiang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (22)
[22] Efficient synthesis of the hexasaccharide fragment of landomycin A:: Using phenyl 2,3-O-thionocarbonyl-1-thioglycosides as 2-deoxy-β-glycoside precursors
Yu, B
Wang, P
ORGANIC LETTERS, 2002, 4 (11) : 1919 - 1922
[23] Fe(III)-catalyzed stereoselective synthesis of deoxyglycosides using stable bifunctional deoxy-phenylpropiolate glycoside donors
Aghi, Anjali
Sau, Sankar
Kumar, Amit
CARBOHYDRATE RESEARCH, 2024, 536
[24] A novel immobilization enzymatic system of nanocellulose-based β-glucosidase in O-glycoside bioconversion of phytochemicals
Cui, Jihong
Fu, Lina
Zhou, Quan
Zhang, Jiaqi
Zhang, Xinlin
Yang, Jie
Fu, Yujie
CELLULOSE, 2025, 32 (05) : 3043 - 3054
[25] Glycals in the stereoselective synthesis of triterpene 2-deoxy-α-L-glycosides under conditions of acidic catalysis
Flekhter, OB
Baltina, LA
Tolstikov, GA
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (07): : 992 - 994
[26] Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides
Meng, Shuai
Zhong, Wenhe
Yao, Wang
Li, Zhongjun
ORGANIC LETTERS, 2020, 22 (08) : 2981 - 2986
[27] First stereoselective synthesis of 2-deoxy-α-D-ribosyl-1-phosphate:: Novel application of crystallization-induced asymmetric transformation
Komatsu, H
Awano, H
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15): : 5419 - 5421
[28] A Metal-Free β-Stereoselective Synthesis of 2-Deoxy- C -arylglycosides: Synthesis of 5-Aza Analogues of Aquayamycin
Mei, Yuling
Jiang, Nan
Yang, Yu
Zhang, Wan
Qiu, Saifeng
Guo, Hong
Zhang, Jianbo
SYNLETT, 2021, 32 (20) : 2075 - 2079
[29] 2-Deoxyglycosyl 3-benzoylpropionates as novel donors for the direct and stereoselective synthesis of 2-deoxy-glycosides
Bandi, Ramakrishna
Chalapala, Sudharani
Chandrasekaran, Srinivasan
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (13) : 2248 - 2257
[30] 4-O-acetyl-3-O-tert-butyldimethylsilyl-L-rhamnal:: a building block in the stereoselective synthesis of 2-deoxy-α-L-rhamnopyranosides
Wandzik, Ilona
Bieg, Tadeusz
CARBOHYDRATE RESEARCH, 2006, 341 (16) : 2702 - 2707

← 1 2 3 4 5 →