EXTREMELY MILD AND SELECTIVE METHOD FOR HYDROLYSIS OF TOSYL ESTERS BY PHOTO-SENSITIZED SINGLE ELECTRON-TRANSFER REACTIONS

被引：8

作者：

NISHIDA, A

HAMADA, T

YONEMITSU, O

机构：

[1] Faculty Of Pharmaceutical Sciences, Hokkaido University

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1990年 / 38卷 / 11期

关键词：

electron-rich aromatic compound; hydrolysis; nucleoside; photo-sensitization; single electron; sugar; tosyl ester; transfer; UV irradiation;

D O I：

10.1248/cpb.38.2977

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Tosyl esters were hydrolyzed by irradiation with ultraviolet light (>330nm) under photo-sensitized conditions. 1,5-Dimethoxynaphthalene and (4,8-dimethoxynaphthyl)propionic acid were effective for the transformation in aqueous acetonitrile in the presence of hydrazine. The reaction was successfully applied to the hydrolysis of tosylates of sugars and nucleosides. © 1990, The Pharmaceutical Society of Japan. All rights reserved.

引用

页码：2977 / 2980

页数：4

共 20 条

[11] MASNOVI J, 1987, J AM CHEM SOC, V109, P2951
[12] NAITO T, 1968, CHEM PHARM BULL, V16, P285
[13] HYDROLYSIS OF TOSYL ESTERS INITIATED BY AN ELECTRON-TRANSFER FROM PHOTOEXCITED ELECTRON-RICH AROMATIC-COMPOUNDS
NISHIDA, A
HAMADA, T
YONEMITSU, O
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) : 3386 - 3387
[14] NODA I, 1988, THESIS HOKKAIDO U
[15] SYNTHESIS OF OLIGORIBONUCLEOTIDES .2. USE OF SILYL PROTECTING GROUPS IN NUCLEOSIDE AND NUCLEOTIDE CHEMISTRY .7.
OGILVIE, KK
BEAUCAGE, SL
SCHIFMAN, AL
THERIAULT, NY
SADANA, KL
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1978, 56 (21): : 2768 - 2780
[16] REHM D, 1970, ISRAEL J CHEM, V8, P259
[17] PREPARATION AND SYNTHETIC UTILITY OF SOME ORGANOTIN DERIVATIVES OF NUCLEOSIDES
WAGNER, D
VERHEYDEN, JP
MOFFATT, JG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (01) : 24 - 30
[18] SALT EFFECTS AND ION PAIRS IN SOLVOLYSIS AND RELATED REACTIONS .3. COMMON ION RATE DEPRESSION AND EXCHANGE OF ANIONS DURING ACETOLYSIS
WINSTEIN, S
CLIPPINGER, E
FAINBERG, AH
HECK, R
ROBINSON, GC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (02) : 328 - 335
[19] PHOTOLYSIS OF SUGAR TOSYLATE . A NEW PROCEDURE DE-O-TOSYLATION
ZEN, S
TASHIMA, S
KOTO, S
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1968, 41 (12) : 3025 - +
[20] OXIDATION REDUCTION AND ELECTROCHEMILUMINESCENCE OF DONOR-SUBSTITUTED POLYCYCLIC AROMATIC HYDROCARBONS
ZWEIG, A
MAURER, AH
ROBERTS, BG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (05) : 1322 - &

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