Synthesis of S-glycosyl thiophosphates, thiophosphonates and thiophosphinates by the Michaelis-Arbuzov rearrangement of anomeric thiocyanates

被引：21

作者：

Piekutowska, Marta ^{[1
]}

Pakulski, Zbigniew ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

来源：

CARBOHYDRATE RESEARCH | 2008年 / 343卷 / 04期

关键词：

thiocyanates; thiophosphates; thiophosphonates; thiophosphinates; glycosyl donors;

D O I：

10.1016/j.carres.2007.12.009

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Reaction of anomeric thiocyanates with a series of O-alkyl or O-trimethylsilyl phosphite, phenylphosphonite and diphenyl-phosphinite derivatives afforded the corresponding S-glycosyl thiophosphates, thiophosphonates and thiophosphinates in good yields. These derivatives had been previously applied as glycosyl donors in the synthesis of benzyl glycosides and disaccharides with excellent stereo selectivity. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：785 / 792

页数：8

共 58 条

[31]

Kudelska W, 1997, POL J CHEM, V71, P1548

[32]

Kudelska W, 1998, Z NATURFORSCH B, V53, P1277

[33] The cyanation reaction of O-acetylated S-glycosyl phosphorothioates [J].

Kudelska, W .

CARBOHYDRATE RESEARCH, 2000, 329 (03) :687-691

[34] Synthesis of stable dolichylphosphomannose analogues [J].

Kulesza, A ;

Frank, CG ;

Aebi, M ;

Vasella, A .

HELVETICA CHIMICA ACTA, 2004, 87 (12) :3106-3118

[35] EFFICIENT SYNTHESIS OF S-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOSYL) AND SE-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOSYL) THIOPHOSPHATES AND SELENOPHOSPHATES [J].

LIPKA, P ;

MICHALSKA, M .

CARBOHYDRATE RESEARCH, 1983, 113 (02) :317-320

[36]

MICHALSKA M, 1974, B ACAD POL SCI-CHIM, V22, P1053

[37] GLYCOSYLATION OF ORGANIC THIOACIDS AND SELENOACIDS OF PHOSPHORUS - REACTION OF ORGANIC MONOTHIO ACIDS OF PHOSPHORUS WITH GLYCOSYL BROMIDES - THIONO-THIOLO REARRANGEMENT OF GLYCOSYL PHOSPHOROTHIOATES [J].

MICHALSKA, M ;

MICHALSKI, J ;

ORLICH, I .

TETRAHEDRON, 1978, 34 (05) :617-622

[38]

MICHALSKI J, 1956, B ACAD POL SCI, V4, P279

[39] THE SYNTHESIS AND CHARACTERIZATION OF 2-O-(6-O-L-GLYCERO-ALPHA,BETA-D-MANNO-HEPTOPYRANOSYL-ALPHA-D-GLUCOPYRANOSYL)-ALPHA,BETA-D-GLUCOPYRANOSE [J].

NEPOGODEV, SA ;

PAKULSKI, Z ;

ZAMOJSKI, A ;

HOLST, O ;

BRADE, H .

CARBOHYDRATE RESEARCH, 1992, 232 (01) :33-45

[40]

NURETDINOVA ON, 1992, IZV AKAD K, P2673

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