AN EFFICIENT METHOD FOR THE DEPROTECTION OF ALLYL GLYCOSIDES WITH ADJACENT AZIDES - THE CIRCUMVENTION OF UNWANTED DIPOLAR CYCLOADDITION PRODUCTS

被引：25

作者：

LAMBERTH, C

BEDNARSKI, MD

机构：

[1] UNIV CALIF BERKELEY,LAWRENCE BERKELEY LAB,CTR ADV MAT,BERKELEY,CA 94720

[2] UNIV CALIF BERKELEY,DEPT CHEM,BERKELEY,CA 94720

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 50期

关键词：

ALLYL GLYCOSIDE; DEPROTECTION; DIPOLAR CYCLOADDITION;

D O I：

10.1016/0040-4039(91)80109-J

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A two step deallylation scheme using (bis(methyldiphenylphosphine)) (1,5-cyclooctadiene) iridium (I) hexafluorophosphate and catalytic amounts of osmium tetroxide with trimethylamine N-oxide is used to deprotect allyl glycosides in the presence of an azide group at C-2. This method avoids the formation of intramolecular 1,3-dipolar cycloaddition products which are isolated during the deprotection using other procedures.

引用

页码：7369 / 7372

页数：4

共 37 条

[1] BOMMER R, 1991, LIEBIGS ANN CHEM, P425
[2] CLEAVAGE OF ALLYL ETHERS WITH PD-C
BOSS, R
SCHEFFOLD, R
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (09): : 558 - 559
[3] SYNTHESIS AND CHARACTERIZATION OF PROPYL O-BETA-D-GALACTOPYRANOSYL-(1-]4)-O-BETA-D-GALACTOPYRANOSYL-(1-]4)-ALPHA-D-GALACTOPYRANOSIDE
ELSHENAWY, HA
SCHUERCH, C
[J]. CARBOHYDRATE RESEARCH, 1984, 131 (02) : 239 - 246
[4] INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITIONS OF ARYL AZIDES BEARING ALKENYL, ALKYNYL, AND NITRILE GROUPS
FUSCO, R
GARANTI, L
ZECCHI, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (13) : 1906 - 1909
[5] ALLYL ETHER AS A PROTECTING GROUP IN CARBOHYDRATE-CHEMISTRY .8. SYNTHESIS OF BENZYL AND ALLYL ETHERS OF D-GLUCOPYRANOSE
GENT, PA
GIGG, R
[J]. CARBOHYDRATE RESEARCH, 1976, 49 (JUL) : 325 - 333
[6] GIGG R, 1978, ACS SYM SER, V77, P44
[7] GIGG R, 1977, ACS SYM SER, V39, P253
[8] GRUNDLER G, 1984, LIEBIGS ANN CHEM, P1826
[9] SYNTHESIS OF COMPOUNDS DESIGNED TO INHIBIT BACTERIAL-CELL WALL TRANSGLYCOSYLATION
HECKER, SJ
MINICH, ML
LACKEY, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (16) : 4904 - 4911
[10] HORITO S, 1986, LIEBIGS ANN CHEM, P1880

← 1 2 3 4 →