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

[21] Synthesis of Nucleosides and Deoxynucleosides via Gold(I)- Catalyzed N-Glycosylation of Glycosyl (Z)-Ynenoates
Liu, Rongkun
Chen, Yan
Zheng, Jibin
Zhang, Lvfeng
Xu, Tong
Xu, Peng
Yang, You
ORGANIC LETTERS, 2022, 24 (51) : 9479 - 9484
[22] 2-Deoxy-2-iodo-β-glucopyranosyl fluorides:: Mild and highly stereoselective glycosyl donors for the synthesis of 2-deoxy-β-glycosides from β-hydroxy ketones
Blanchard, N
Roush, WR
ORGANIC LETTERS, 2003, 5 (01) : 81 - 84
[23] RADICAL REARRANGEMENT OF 2-O-(DIPHENYLPHOSPHORYL)GLYCOSYL BROMIDES - A NEW SYNTHESIS FOR 2-DEOXY DISACCHARIDES AND 2-DEOXY RIBONUCLEOSIDES
KOCH, A
LAMBERTH, C
WETTERICH, F
GIESE, B
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05): : 1083 - 1089
[24] AN ATTEMPT AT THE DIRECT CONSTRUCTION OF 2-DEOXY-BETA-GLYCOSIDIC LINKAGES CAPITALIZING ON 2-DEOXYGLYCOPYRANOSYL DIETHYL PHOSPHITES AS GLYCOSYL DONORS
HASHIMOTO, S
SANO, A
SAKAMOTO, H
NAKAJIMA, M
YANAGIYA, Y
IKEGAMI, S
SYNLETT, 1995, (12) : 1271 - +
[25] Synthesis of a 2-N,N-dibenzylamino glucopyranosyl trichloroacetimidate glycosyl donor and evaluation of its utility in stereoselective glycosylation
Ali, Stacy P.
Jalsa, Nigel Kevin
CARBOHYDRATE RESEARCH, 2016, 420 : 13 - 22
[26] SYNTHESIS OF 6-SUBSTITUTED PURINE N-7-(2-DEOXY-BETA-D-RIBONUCLEOSIDES) VIA ANION GLYCOSYLATION AND ANOMERIZATION DURING THE N-7/N-9-GLYCOSYL TRANSFER
SEELA, F
WINTER, H
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1995, 14 (1-2): : 129 - 142
[27] Efficient stereoselective synthesis of N-linked glycopeptides by N-glycosylation of primary amide groups.
Tanaka, H
Iwata, Y
Takahashi, D
Adachi, M
Takahashi, T
GLYCOBIOLOGY, 2004, 14 (11) : 1088 - 1088
[28] Enzymatic Synthesis of 2′-Deoxy-β-D-ribonucleosides of 8-Azapurines and 8-Aza-7-deazapurines
Stepchenko, Vladimir A.
Seela, Frank
Esipov, Roman S.
Miroshnikov, Anatoly I.
Sokolov, Yuri A.
Mikhailopulo, Igor A.
SYNLETT, 2012, (10) : 1541 - 1545
[29] Highly stereoselective synthesis of 2-deoxy-α-glycosides and α-disaccharides
Bielawska, H
Michalska, M
TETRAHEDRON LETTERS, 1998, 39 (52) : 9761 - 9764
[30] Phenyl 2-azido-2-deoxy-1-selenogalactosides: a single type of glycosyl donor for the highly stereoselective synthesis of α- and β-2-azido-2-deoxy-D-galactopyranosides
Khatuntseva, Elena A.
Sherman, Andrey A.
Tsvetkov, Yury E.
Nifantiev, Nikolay E.
TETRAHEDRON LETTERS, 2016, 57 (06) : 708 - 711

← 1 2 3 4 5 →