CYCLOGLYCOSIDATION OF 1,2-UNSATURATED MALTOHEXAOSE AND MALTOHEPTAOSE DERIVATIVES WITH IODONIUM ADDITION - CONVERSION OF ALPHA-CYCLODEXTRINS AND BETA-CYCLODEXTRINS INTO MONO(2-DEOXY) DERIVATIVES VIA ACYCLIC INTERMEDIATES

被引：15

作者：

SAKAIRI, N ^{[1
]}

KUZUHARA, H ^{[1
]}

机构：

[1] INST PHYS & CHEM RES,WAKO,SAITAMA 35101,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1992年 / 06期

关键词：

D O I：

10.1039/c39920000510

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Iodonium ion treatment of 1,2-unsaturated heptadeca-O-benzylmaltohexaose and icosa-O-benzylmaltoheptaose derivatives derived from alpha- and beta-cyclodextrins brought about their recyclization by intramolecular glycosidation, giving mono(2-deoxy-2-iodo)-alpha- and -beta-cyclodextrin derivatives, which were converted into mono(2-deoxy)-alpha- and -beta-cyclodextrins by radical reduction.

引用

页码：510 / 512

页数：3

共 10 条

[1] A NEW CYCLOGLUCOHEXAOSE DERIVATIVE - THE CHEMICAL SYNTHESIS OF CYCLO(-]3-[BETA-D-GLCP-(1-]3)-]5-D-GLCP-(1-])
COLLINS, PM
ALI, MH
[J]. TETRAHEDRON LETTERS, 1990, 31 (31) : 4517 - 4520
[2] PREPARATION OF PYRANOID GLYCAL DERIVATIVES FROM PHENYL THIOGLYCOSIDES AND GLYCOSYL PHENYL SULFONES
FERNANDEZMAYORALAS, A
MARRA, A
TRUMTEL, M
VEYRIERES, A
SINAY, P
[J]. CARBOHYDRATE RESEARCH, 1989, 188 : 81 - 95
[3] SYNTHESIS OF BETA-D-GLUCOPYRANOSYL 2-DEOXY-ALPHA-D-ARABINO-HEXOPYRANOSIDE
LEMIEUX, RU
MORGAN, AR
[J]. CANADIAN JOURNAL OF CHEMISTRY, 1965, 43 (08): : 2190 - &
[4] STEREOSELECTIVITY OF CYCLOGLYCOSYLATION IN MANNOOLIGOSE SERIES DEPENDS ON CARBOHYDRATE CHAIN-LENGTH - SYNTHESES OF MANNO ISOMERS OF BETA-CYCLODEXTRINS AND GAMMA-CYCLODEXTRINS
MORI, M
ITO, Y
UZAWA, J
OGAWA, T
[J]. TETRAHEDRON LETTERS, 1990, 31 (22) : 3191 - 3194
[5] A HIGHLY EFFICIENT AND STEREOSELECTIVE CYCLOGLYCOSYLATION - SYNTHESIS OF CYCLO(-]4)-[ALPHA-MAN-(1-]4)]5-ALPHA-MAN-(1-]), A MANNO ISOMER OF ALPHA-CYCLODEXTRIN
MORI, M
ITO, Y
OGAWA, T
[J]. TETRAHEDRON LETTERS, 1989, 30 (10) : 1273 - 1276
[6] TOTAL SYNTHESIS OF CYCLO-L-RHAMNOHEXAOSE BY A STEREOSELECTIVE THERMAL GLYCOSYLATION
NISHIZAWA, M
IMAGAWA, H
KAN, Y
YAMADA, H
[J]. TETRAHEDRON LETTERS, 1991, 32 (40) : 5551 - 5554
[7] INSERTION OF A D-GLUCOSAMINE RESIDUE INTO THE ALPHA-CYCLODEXTRIN SKELETON - A MODEL SYNTHESIS OF CHIMERA CYCLODEXTRINS
SAKAIRI, N
WANG, LX
KUZUHARA, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (05) : 289 - 290
[8] APPLICATION OF SUBSTITUENT-CONTROLLED OXIDATIVE COUPLING OF GLYCALS IN A SYNTHESIS AND STRUCTURAL CORROBORATION OF CICLAMYCIN-0 - NEW POSSIBILITIES FOR THE CONSTRUCTION OF HYBRID ANTHRACYCLINES
SUZUKI, K
SULIKOWSKI, GA
FRIESEN, RW
DANISHEFSKY, SJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (24) : 8895 - 8902
[9] GLUCAN SYNTHESIS .6. TOTAL SYNTHESIS OF CYCLOMALTOHEXAOSE
TAKAHASHI, Y
OGAWA, T
[J]. CARBOHYDRATE RESEARCH, 1987, 164 : 277 - 296
[10] THIEM J, 1989, ACS S SERIES, V386

← 1 →