High-Yield Syntheses of Tetra-O-benzyl-α-D-glucopyranosyl bromide and Tetra-O-pivaloyl-α-D-glucopyranosyl bromide and their Advantage in the Koenigs-Knorr Reaction

被引：0

作者：

Armin Presser

Olaf Kunert

Irmgard Pötschger

机构：

[1] Institute of Pharmaceutical Sciences,Department of Pharmaceutical Chemistry

[2] Karl-Franzens-University of Graz,undefined

来源：

Monatshefte für Chemie / Chemical Monthly | 2006年 / 137卷

关键词：

Keywords. ; -; reaction; Glycosidation; Orthoester; Cholesteryl glycosides.;

D O I：

暂无

中图分类号：

学科分类号：

摘要：

Several improved approaches for the preparation of tetra-O-benzyl-α-D-glucopyranosyl bromide and tetra-O-pivaloyl-α-D-glucopyranosyl bromide are discussed. The importance of these compounds, which are useful glycosyl donors, was demonstrated by successful preparation of cholesteryl glucopyranosides in an almost neutral medium without the formation of orthoesters. In addition, accurate 1H and 13C NMR resonance assignments of the synthesized cholesteryl glycosides were performed by 2D NMR spectroscopy.

引用

页码：365 / 374

页数：9

共 50 条

[31] N-glycoside neoglycotrimers from 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl azide
Temelkoff, David P.
Zeller, Matthias
Norris, Peter
CARBOHYDRATE RESEARCH, 2006, 341 (09) : 1081 - 1090
[32] N-substituted-N′-(2′,3′,4′,6′-tetra-O-acetyl)-β-D-glucopyranosyl thiocarbamides and thiosemicarbazides
Li, M
Wen, LR
Jing, SX
Zhang, YB
Yang, HZ
Zhang, SS
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2001, 21 (12) : 1137 - 1141
[33] CONVENIENT PREPARATION OF 2,3,4,6-TETRA-O-METHYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE
BATES, HA
SELICK, C
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1985, 4 (02) : 273 - 275
[34] Ultrasound-assisted reaction of 2,3,4,6-tetra-0-acetyl-α-D-glucopyranosyl bromide with potassium salt of curcumin under PTC conditions
Parvathy, Kattera S.
Srinivas, Pullabhatla
ULTRASONICS SONOCHEMISTRY, 2008, 15 (04) : 571 - 577
[35] KOENIGS-KNORR REACTIONS .2. A MECHANISTIC STUDY OF MERCURY(II) CYANIDE-PROMOTED REACTIONS OF 2,3,4,6-TETRA-O-METHYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE WITH CYCLOHEXANOL IN BENZENE-NITROMETHANE
WALLACE, JE
SCHROEDER, LR
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1976, (14): : 1632 - 1636
[36] Synthesis and antibacterial and antifungal activities of N-(tetra-O-acetyl-β-d-glucopyranosyl)thiosemicarbazones of substituted 4-formylsydnones
Nguyen Dinh Thanh
Hoang Thanh Duc
Vu Thi Duyen
Phan Manh Tuong
Nguyen Van Quoc
Chemistry Central Journal, 9
[37] Solid-state structure of methyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-galactopyranoside and methyl 3,4,6-tri-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-galactopyranoside
Gubica, Tomasz
Bukowicki, Jaroslaw
Stepien, Dorota K.
Ostrowski, Andrzej
Pisklak, Dariusz M.
Cyranski, Michal K.
JOURNAL OF MOLECULAR STRUCTURE, 2013, 1037 : 49 - 56
[38] Sc(OTf)3 efflciently catalyzed the glycosidation of 1-C-alkyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl acetates with alcohols
Yamanoi, T
Oda, Y
Yamazaki, I
Shinbara, M
Morimoto, K
Matsuda, S
LETTERS IN ORGANIC CHEMISTRY, 2005, 2 (03) : 242 - 246
[39] SYNTHESIS AND PROPERTIES OF 2,3,4,6-TETRA-O-ACETYL-5-THIO-ALPHA-D-GLUCOPYRANOSYL AND 2,3,4,6-TETRA-O-ACETYL-5-THIO-BETA-D-GLUCOPYRANOSYL BROMIDE
KORYTNYK, W
VALENTEKOVICHORVATH, S
DODSONSIMMONS, O
CARBOHYDRATE RESEARCH, 1982, 108 (02) : 293 - 297
[40] Synthesis, antifungal activities, and potential detoxification of N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamates
Zhou, Yaling
Wang, Li
Han, Lixia
Meng, Fangui
Yang, Chunlong
CARBOHYDRATE RESEARCH, 2009, 344 (11) : 1289 - 1296

← 1 2 3 4 5 →