Guanidine/guanidinium nitrate; A mild and selective O-deacetylation reagent that leaves the N-Troc group intact.

被引：79

作者：

Ellervik, U ^{[1
]}

Magnusson, G ^{[1
]}

机构：

[1] LUND UNIV,LUND INST TECHNOL,CTR CHEM & CHEM ENGN,S-22100 LUND,SWEDEN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(97)00105-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of O-acetyl-protected sugars with a methanolic solution of guanidine/guanidinium nitrate caused the removal of the acetyl groups (91-99% isolated yield), without affecting other protecting groups. Removal of O-benzoyl groups required a longer reaction time. Of special merit is the stability of the 2,2,2-trichloroethoxycarbonylamino (N-Troc) group under these weakly basic reaction conditions. (C) 1997 Elsevier Science Ltd.

引用

页码：1627 / 1628

页数：2

共 10 条

[1] LIPASE-CATALYZED IRREVERSIBLE TRANSESTERIFICATION USING ENOL ESTERS - RESOLUTION OF PROSTAGLANDIN SYNTHONS 4-HYDROXY-2-ALKYL-2-CYCLOPENTENONES AND INVERSION OF THE 4S ENANTIOMER TO THE 4R ENANTIOMER [J].

BABIAK, KA ;

NG, JS ;

DYGOS, JH ;

WEYKER, CL ;

WANG, YF ;

WONG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3377-3381

[2] Glycosylation with N-Troc-protected glycosyl donors [J].

Ellervik, U ;

Magnusson, G .

CARBOHYDRATE RESEARCH, 1996, 280 (02) :251-260

[3]

ELLERVIK U, UNPUB

[4]

KUNESCH N, 1994, LIEBIGS ANN CHEM, P1059

[5] MILD, RAPID AND SELECTIVE DEPROTECTION OF ACETYLATED CARBOHYDRATES AND PHENOLS WITH GUANIDINE [J].

KUNESCH, N ;

MIET, C ;

POISSON, J .

TETRAHEDRON LETTERS, 1987, 28 (31) :3569-3572

[6] CHEMICAL SYNTHESIS OF 1-DEPHOSPHO DERIVATIVE OF ESCHERICHIA-COLI LIPID-A [J].

KUSUMOTO, S ;

YOSHIMURA, H ;

IMOTO, M ;

SHIMAMOTO, T ;

SHIBA, T .

TETRAHEDRON LETTERS, 1985, 26 (07) :909-912

[7] CATALYTIC STEREOSELECTIVE SYNTHESIS OF 2-AMINO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDES AND GALACTOPYRANOSIDES [J].

MATSUBARA, K ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1993, (12) :2145-2148

[8] STEREOSELECTIVE SYNTHESIS OF 2-AMINO-2-DEOXY-BETA-D-GLUCOPYRANOSIDES AND GALACTOPYRANOSIDES BY USING A CATALYTIC AMOUNT OF TIN(II) TRIFLUOROMETHANESULFONATE [J].

MUKAIYAMA, T ;

MATSUBARA, K .

CHEMISTRY LETTERS, 1992, (09) :1755-1758

[9] ENZYMATIC GLYCOSYLATION OF O-GLYCOPEPTIDES [J].

SCHULTZ, M ;

KUNZ, H .

TETRAHEDRON LETTERS, 1992, 33 (37) :5319-5322

[10]

WINDHOLZ TB, 1967, TETRAHEDRON LETT, V27, P2555

← 1 →