Use of cyclic sulfamidates derived from D-allosamine in nucleophilic displacements: Scope and limitations

被引：45

作者：

Aguilera, B ^{[1
]}

FernandezMayoralas, A ^{[1
]}

Jaramillo, C ^{[1
]}

机构：

[1] CSIC,INST QUIM ORGAN,DEPT QUIM ORGAN BIOL,E-28006 MADRID,SPAIN

来源：

TETRAHEDRON | 1997年 / 53卷 / 16期

关键词：

D O I：

10.1016/S0040-4020(97)00246-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cyclic 2,3-sulfamidate derived from N-acetyl-D-allosamine has been treated with a variety of S-, N-, O-, and C-nucleophiles, leading to nucleophilic displacement at C-3, elimination, or deacetylation reactions depending on the type of nucleophile used. Nucleophilic displacement is achieved with thio-nucleophiles and NaN3, allowing the preparation of 3-thio- or 3-azido glucosamine derivatives difficult to obtain by use of sulfonates. (C) 1997 Elsevier Science Ltd.

引用

页码：5863 / 5876

页数：14

共 26 条

[1] Nucleophilic displacements on a cyclic sulfamidate derived from allosamine: Application to the synthesis of thiooligosaccharides
Aguilera, B
FernandezMayoralas, A
[J]. CHEMICAL COMMUNICATIONS, 1996, (02) : 127 - 128
[2] THE DIRECT SYNTHESIS OF THE CYCLIC SULPHAMIDATE OF (S)-PROLINOL - SIMULTANEOUS N-PROTECTION AND ACTIVATION TOWARDS NUCLEOPHILIC DISPLACEMENT OF OXYGEN
ALKER, D
DOYLE, KJ
HARWOOD, LM
MCGREGOR, A
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (12) : 877 - 880
[3] CYCLIC SULPHAMIDATES - NEW SYNTHETIC PRECURSORS FOR BETA-FUNCTIONALIZED ALPHA-AMINO-ACIDS
BALDWIN, JE
SPIVEY, AC
SCHOFIELD, CJ
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (12) : 881 - 884
[4] Syntheses with glucosamine.
Bergmann, M
Zervas, L
[J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1931, 64 : 975 - 980
[5] SYNTHESIS AND REACTIONS OF CARBOHYDRATE TRIFLUOROMETHANESULFONATES (CARBOHYDRATE TRIFLATES)
BINKLEY, RW
AMBROSE, MG
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1984, 3 (01) : 1 - 49
[6] A CONVENIENT METHOD FOR S-GLYCOSIDIC BOND FORMATION - SYNTHESIS OF PARA-IODOPHENYL 4'-THIOMALTOTRIOSIDE AND ITS 2'',3''-UNSATURATED ANALOG
BLANCMUESSER, M
DRIGUEZ, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (12): : 3345 - 3351
[7] SYNTHESES OF THE FUNGICIDE/INSECTICIDE ALLOSAMIDIN AND A STRUCTURAL ISOMER
BLATTNER, R
FURNEAUX, RH
KEMMITT, T
TYLER, PC
FERRIER, RJ
TIDEN, AK
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (23): : 3411 - 3421
[8] CONVERSION OF 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSE (N-ACETYLGLUCOSAMINE) INTO 2-ACETAMIDO-2-DEOXY-BETA-D-GALACTOPYRANOSE (N-ACETYLGALACTOSAMINE) USING A BIOTRANSFORMATION TO GENERATE A SELECTIVELY DEPROTECTED SUBSTRATE FOR SN2 INVERSION
CHAPLIN, D
CROUT, DHG
BORNEMANN, S
HUTCHINSON, DW
KHAN, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (02): : 235 - 237
[9] OLIGOSACCHARIDES STRUCTURALLY RELATED TO E-SELECTIN LIGANDS ARE INHIBITORS OF NEURAL CELL-DIVISION - SYNTHESIS, CONFORMATIONAL-ANALYSIS, AND BIOLOGICAL-ACTIVITY
COTERON, JM
SINGH, K
ASENSIO, JL
DOMINGUEZDALDA, M
FERNANDEZMAYORALAS, A
JIMENEZBARBERO, J
MARTINLOMAS, M
ABADRODRIGUEZ, J
NIETOSAMPEDRO, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) : 1502 - 1519
[10] Defaye J., 1991, STUDIES NATURAL PROD, V8, P315

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