N-glycosylation with glycosyl diethyl phosphites:: A highly stereoselective synthesis of 2′-deoxy-β-ribonucleosides

被引：13

作者：

Hashimoto, S ^{[1
]}

Inagaki, J ^{[1
]}

Sakamoto, H ^{[1
]}

Sano, A ^{[1
]}

Nakajima, M ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 060, Japan

来源：

HETEROCYCLES | 1997年 / 46卷

关键词：

D O I：

10.3987/COM-97-S80

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and direct method for the construction of 2'-deoxy-beta-N-glycosidic linkages in 2'-deoxyribonucleoside synthesis has been developed by using 3-(3,4,5-trimethoxybenzoyl)-protected 2-deoxyribofuranosyl diethyl phosphites as a glycosyl donor in the presence of trimethylsilyl triflate, wherein coupling reactions with silylated pyrimidine bases have been found to exhibit beta-selectivities up to 96%.

引用

页码：215 / 220

页数：6

共 50 条

[1] A dramatic concentration effect on the stereoselectivity of N-glycosylation for the synthesis of 2′-deoxy-β-ribonucleosides
Yang, Fei
Zhu, Yugen
Yu, Biao
CHEMICAL COMMUNICATIONS, 2012, 48 (56) : 7097 - 7099
[2] Highly stereoselective synthesis of 2′-deoxy-β-ribonucleosides via a 3′-(N-acetyl)-glycyl-directing group
Liu, Zhaogui
Li, Deyao
Yin, Biaolin
Zhang, Jiancun
TETRAHEDRON LETTERS, 2010, 51 (02) : 240 - 243
[3] Highly Stereoselective Synthesis of 2'-Deoxy-a-ribonucleosides and 2-Deoxy-a-C-ribofuranosides by Remote Stereocontrolled Glycosylation
Chem Lett, 4 (389):
[4] Highly stereoselective synthesis of 2'-deoxy-alpha-ribonucleosides and 2-deoxy-alpha-C-ribofuranosides by remote stereocontrolled glycosylation
Mukaiyama, T
Ishikawa, T
Uchiro, H
CHEMISTRY LETTERS, 1997, (04) : 389 - 390
[5] Efficient stereoselective synthesis of γ-N-glycosyl asparagines by N-glycosylation of primary amide groups
Tanaka, H
Iwata, Y
Takahashi, D
Adachi, M
Takahashi, T
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (06) : 1630 - 1631
[6] Efficient stereoselective synthesis of γ-N-glycosyl asparagines by N-glycosylation of primary amide groups
Tanaka, Hiroshi
Iwata, Yuki
Takahashi, Daisuke
Adachi, Masaatsu
Takahashi, Takashi
Journal of the American Chemical Society, 2005, 127 (06): : 1630 - 1631
[7] STEREOSELECTIVE SYNTHESIS OF INDAZOLE 2'-DEOXY-BETA-D-RIBONUCLEOSIDES - GLYCOSYLATION OF THE NUCLEOBASE ANION
SEELA, F
BOURGEOIS, W
HELVETICA CHIMICA ACTA, 1991, 74 (02) : 315 - 322
[8] SYNTHESIS OF β-GLYCOSYL FORMAMIDES THROUGH N-GLYCOSYLATION OF UNPROTECTED CARBOHYDRATES
Ichikawa, Yoshiyasu
Matsukawa, Akihito
Maeda, Mitsutoshi
Tomita, Yumiko
Mimura, Rika
Kitamori, Ayumi
Kotsuki, Hiyoshizo
Nakano, Keiji
Masuda, Toshiya
HETEROCYCLES, 2016, 92 (12) : 2201 - 2212
[9] Stereoselective N-Glycosylation of 2-Deoxythioribosides for Fluorescent Nucleoside Synthesis
Mata, Guillaume
Luedtke, Nathan W.
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (20): : 9006 - 9017
[10] A novel approach to synthesis of 2′-deoxy-β-D-ribonucleosides via transglycosylation of 6-oxopurine ribonucleosides
Boryski, J
NUCLEOSIDES & NUCLEOTIDES, 1998, 17 (9-11): : 1547 - 1556

← 1 2 3 4 5 →