SYNTHESIS AND CHEMICAL TRANSFORMATION OF 2-ACETOXYIMINO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-ARABINO-HEXOPYRANOSYL AZIDE

被引：6

作者：

WALCZYNA, R ^{[1
]}

SMIATACZ, Z ^{[1
]}

CIUNIK, Z ^{[1
]}

机构：

[1] WROCLAW UNIV,INST CHEM,PL-50383 WROCLAW,POLAND

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1993年 / 12卷 / 08期

关键词：

D O I：

10.1080/07328309308020125

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：

The title compound 3 has been synthesized from 3,4, 6-tri-O-acetyl-2-deoxy-2-nitroso-alpha-D-glucopyranosyl chloride (1) via compound 2. Azide reduction of 3 is accompanied by O-->N-acetyl migration to afford N-acetyl-N- (3, 4, 6-tri-O-acetyl-2-deoxy-2-hydroxyimino-beta-D-arabino-hexopyranosyl)amine (4) , also characterized as its Z and E peracetates. on the basis of IR, H-1 NMR and X-ray structural data from compound 4, its beta-NHAc configuration, (Z) 2-hydroxyimino, and degrees-S2 conformation, were established.

引用

页码：1161 / 1171

页数：11

共 50 条

[1] SYNTHESIS OF 3,4,6-TRI-O-ACETYL AND 3,4,6-TRI-O-BENZOYL DERIVATIVES OF 2-DEOXY-ALPHA-D-ARABINO-HEXOPYRANOSYL FLUORIDE
HALL, LD
MANVILLE, JF
[J]. CANADIAN JOURNAL OF CHEMISTRY, 1967, 45 (11): : 1299 - &
[2] EFFICIENT SYNTHESES OF 3,4,6-TRI-O-ACETYL-2-DEOXY-2-PHTHALIMIDO-BETA-D-GALACTOPYRANOSYL AND 3,4,6-TRI-O-ACETYL-2-DEOXY-2-PHTHALIMIDO-ALPHA-D-GALACTOPYRANOSYL CHLORIDE
NILSSON, U
RAY, AK
MAGNUSSON, G
[J]. CARBOHYDRATE RESEARCH, 1990, 208 : 260 - 263
[3] SYNTHESIS OF 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSYLAMINE AND DIMER FORMATION
PAUL, B
KORYTNYK, W
[J]. CARBOHYDRATE RESEARCH, 1978, 67 (02) : 457 - 468
[4] The transformation mechanism of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol in water
Madaj, J
Rak, J
Sokolowski, J
Wisniewski, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09): : 2988 - 2994
[5] ENAMINES DERIVED FROM 3,4,6-TRI-O-ACETYL-2-AMINO-2-DEOXY-ALPHA-D-GLUCOPYRANOSE AND BETA-DICARBONYL COMPOUNDS - SYNTHESIS OF 3,4,6-TRI-O-ACETYL-2-AMINO-2-DEOXY-ALPHA-D-GLUCOPYRANOSE
GOMEZSANCHEZ, A
CERTVENT.A
SCHEIDEG.U
[J]. CARBOHYDRATE RESEARCH, 1971, 18 (02) : 173 - +
[6] CRYSTAL-STRUCTURE OF ETHYL 3,4,6-TRI-O-ACETYL-2-DEOXY-2-HYDROXYIMINO-ALPHA-D-ARABINO-HEXOPYRANOSIDE
CIUNIK, Z
SZWEDA, R
SMIATACZ, Z
[J]. CARBOHYDRATE RESEARCH, 1991, 219 : 9 - 13
[7] ALL ABOUT 3,4,6-TRI-O-ACETYL-2-DEOXY-2-PHTHALIMIDO-BETA-D-GLUCOSYL TRICHLOROACETIMIDATE
BEST, WM
DUNLOP, RW
STICK, RV
WHITE, ST
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (03) : 433 - 440
[8] INTERACTION OF 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSYLAMINE WITH SULFHYDRYL COMPOUNDS
PAUL, B
KORYTNYK, W
[J]. CARBOHYDRATE RESEARCH, 1979, 72 (JUL) : 247 - 256
[9] ETHYL 3,4,6-TRI-O-ACETYL-2-AMINO-2-DEOXY-1-THIO-BETA-D-GLUCOPYRANOSIDE
WOLFROM, ML
CRAMP, WA
HORTON, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (09): : 3056 - &
[10] INTERACTION OF 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSYLAMINE WITH SULFHYDRYL COMPOUNDS
PAUL, B
KORYTNYK, W
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1976, 172 (SEP3): : 143 - 143

← 1 2 3 4 5 →