SYNTHESIS OF 6-AZIDO AND 6-AMINO ANALOGS OF 1-DEOXYNOJIRIMYCIN

被引：12

作者：

KILONDA, A ^{[1
]}

COMPERNOLLE, F ^{[1
]}

TOPPET, S ^{[1
]}

HOORNAERT, GJ ^{[1
]}

机构：

[1] KATHOLIEKE UNIV LEUVEN,DEPT SCHEIKUNDE,ORGAN SYNTH LAB,LOUVAIN HEVERLEE,BELGIUM

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1994年 / 18期

关键词：

D O I：

10.1039/c39940002147

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Selective isopropylidenation of the 2,3- and 5,6-hydroxy groups of 1-[(tert-butoxycarbonyl)amino]-1-deoxy-D-glucitol 5b led to the diacetonide 6 which was converted in seven steps to the selectively protected 6-azido compound 3, a valuable precursor of various derivatives of 6-amino-1,6-dideoxynojirimycin 4b.

引用

页码：2147 / 2148

页数：2

共 17 条

[1] MILD AND SIMPLE BIOMIMETIC CONVERSION OF AMINES TO CARBONYL-COMPOUNDS
BUCKLEY, TF
RAPOPORT, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (16) : 4446 - 4450
[2] A NEW METHOD FOR THE SYNTHESIS OF ORGANIC NITRO-COMPOUNDS
COREY, EJ
SAMUELSSON, B
LUZZIO, FA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (12) : 3682 - 3683
[3] DE CGA, 1992, Patent No. 4819560
[4] ENZYME-CATALYZED ACYLATION OF CASTANOSPERMINE AND 1-DEOXYNOJIRIMYCIN
DELINCK, DL
MARGOLIN, AL
[J]. TETRAHEDRON LETTERS, 1990, 31 (22) : 3093 - 3096
[5] ENZYMATIC-SYNTHESIS OF 4-O-ALPHA-D-GLUCOPYRANOSYL-MORANOLINE
EZURE, Y
[J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1985, 49 (07): : 2159 - 2165
[6] INHIBITION OF HIV REPLICATION BY AMINO-SUGAR DERIVATIVES
FLEET, GWJ
KARPAS, A
DWEK, RA
FELLOWS, LE
TYMS, AS
PETURSSON, S
NAMGOONG, SK
RAMSDEN, NG
SMITH, PW
SON, JC
WILSON, F
WITTY, DR
JACOB, GS
RADEMACHER, TW
[J]. FEBS LETTERS, 1988, 237 (1-2) : 128 - 132
[7] CASTANOSPERMINE, A 1,6,7,8-TETRAHYDROXYOCTAHYDROINDOLIZINE ALKALOID, FROM SEEDS OF CASTANOSPERMUM-AUSTRALE
HOHENSCHUTZ, LD
BELL, EA
JEWESS, PJ
LEWORTHY, DP
PRYCE, RJ
ARNOLD, E
CLARDY, J
[J]. PHYTOCHEMISTRY, 1981, 20 (04) : 811 - 814
[8] STRUCTURE AND SYNTHESIS OF NOJIRIMYCIN
INOUYE, S
TSURUOKA, T
ITO, T
NIIDA, T
[J]. TETRAHEDRON, 1968, 24 (05) : 2125 - &
[9] KHANNA I, 1993, Patent No. 5216168
[10] KINAST G, 1982, Patent No. 49858

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