Selective deprotection of an acetal group in monosaccharide derivatives and related compounds using Me(3)SiCH(2)MgCl

被引：7

作者：

Chen, YH ^{[1
]}

Tseng, YT ^{[1
]}

Luh, TY ^{[1
]}

机构：

[1] NATL TAIWAN UNIV,DEPT CHEM,TAIPEI 106,TAIWAN

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 03期

关键词：

D O I：

10.1039/cc9960000327

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of an acetal of a contiguous diol with Me(3)SiCH(2)MgCl liberates the corresponding diol regioselectively; chelation is used to rationalize the selectivity.

引用

页码：327 / 328

页数：2

共 17 条

[1] Ager D.J., 1990, ORGANIC REACTIONS, V38, P1, DOI DOI 10.1002/0471264180.0R038.01
[2] CONFORMATIONAL-ANALYSIS IN CARBOHYDRATE-CHEMISTRY .4. INTRA-MOLECULAR ACETAL FORMATION BY PRIMARY VERSUS SECONDARY HYDROXYL-GROUPS
ANGYAL, SJ
BEVERIDGE, RJ
[J]. CARBOHYDRATE RESEARCH, 1978, 65 (02) : 229 - 234
[3] NUCLEOPHILIC DISPLACEMENT REACTIONS IN CARBOHYDRATES .V. REACTION OF 2,3-O-ISOPROPYLIDENE-5-O-METHYLSULPHONYL-D-LYXOFURANOSE WITH SODIUM METHOXIDE - ALDEHYDE-GROUP PARTICIPATION
BRIMACOM.JS
HUNEDY, F
TUCKER, LCN
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (12): : 1381 - &
[4] TOTAL SYNTHESIS OF (+/-)-ISOAVENACIOLIDE AND (+/-)-AVENACIOLIDE
BURKE, SD
PACOFSKY, GJ
PISCOPIO, AD
[J]. TETRAHEDRON LETTERS, 1986, 27 (29) : 3345 - 3348
[5] A CONVENIENT SELECTIVE SYNTHESIS OF MONOSACCHARIDE DERIVATIVES HAVING ONLY ONE FREE HYDROXY GROUP
CHEN, YH
LUH, TY
LEE, GH
PENG, SM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (20) : 2369 - 2370
[6] DIFFERENTIATION OF CONTIGUOUS HYDROXYL-GROUPS BY REGIOSELECTIVE CONVERSION OF ACETONIDES INTO TERT-BUTYL HYDROXYALKYL ETHERS
CHENG, WL
YEH, SM
LUH, TY
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) : 5576 - 5577
[7] CARBOHYDRATE CYCLIC ACETAL FORMATION AND MIGRATION
CLODE, DM
[J]. CHEMICAL REVIEWS, 1979, 79 (06) : 491 - 513
[8] THE SYNTHESIS OF METHYL ETHERS OF MANNURONIC AND GLUCURONIC ACID, AND THEIR REACTION WITH PERIODATE
EDINGTON, RA
HIRST, EL
PERCIVAL, EE
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1955, : 2281 - 2288
[9] THE ALLYL GROUP FOR PROTECTION IN CARBOHYDRATE-CHEMISTRY .18. ALLYL AND BENZYL ETHERS OF MYOINOSITOL - INTERMEDIATES FOR THE SYNTHESIS OF MYOINOSITOL TRISPHOSPHATES
GIGG, J
GIGG, R
PAYNE, S
CONANT, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (02): : 423 - 429
[10] DERIVATIVES OF 2,3,4,5,6-PENTA-O-BENZYL-MYO-INOSITOL
GIGG, R
WARREN, CD
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (18): : 2367 - &

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