Facile cleavage of carbohydrate benzyl ethers and benzylidene acetals using the NaBrO3/Na2S2O4 reagent under two-phase conditions

被引:88
作者
Adinolfi, M [1 ]
Barone, G [1 ]
Guariniello, L [1 ]
Iadonisi, A [1 ]
机构
[1] Univ Naples Federico II, Dipartimento Chim Organ & Biol, I-80134 Naples, Italy
关键词
cleavage reactions; carbohydrates;
D O I
10.1016/S0040-4039(99)01756-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Benzyl ether and benzylidene acetal carbohydrate protecting groups can be selectively cleaved by reaction with sodium bromate/sodium dithionite in ethyl acetate/water. Under the mild (room temperature, short reaction time) conditions needed, a variety of other protecting functionalities such as acetyl, chloroacetyl, benzoyl, pivaloyl, tosyl, t-butyldimethylsilyl, trityl, and isopropylidene groups remain unaffected. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8439 / 8441
页数:3
相关论文
共 16 条
[1]  
BIEG T, 1985, SYNTHESIS-STUTTGART, P76
[2]  
BINGLEY RW, 1990, J ORG CHEM, V55, P378
[3]  
BINGLEY RW, 1984, J ORG CHEM, V49, P992
[4]   RAPID REMOVAL OF PROTECTING GROUPS FROM PEPTIDES BY CATALYTIC TRANSFER HYDROGENATION WITH 1,4-CYCLOHEXADIENE [J].
FELIX, AM ;
HEIMER, EP ;
LAMBROS, TJ ;
TZOUGRAKI, C ;
MEIENHOFER, J .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (21) :4194-4196
[5]  
FREIFELDER M, 1978, CATALYTIC HYDROGENAT, P109
[6]   HARD ACID AND SOFT NUCLEOPHILE SYSTEM - NEW EFFICIENT METHOD FOR REMOVAL OF BENZYL PROTECTING GROUP [J].
FUJI, K ;
ICHIKAWA, K ;
NODE, M ;
FUJITA, E .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (10) :1661-1664
[7]  
HANESSIAN S, 1981, SYNTHESIS-STUTTGART, P396
[8]   DEBENZYLATION OF ORTHO-BENZYL-PROTECTED ARALKYL THIOGLUCOSIDES WITH SODIUM LIQUID AMMONIA [J].
HOLICK, SA ;
ANDERSON, L .
CARBOHYDRATE RESEARCH, 1974, 34 (01) :208-213
[9]   USE OF FERRIC-CHLORIDE IN CARBOHYDRATE REACTIONS .4. ACETOLYSIS OF BENZYL ETHERS OF SUGARS [J].
KARTHA, KPR ;
DASGUPTA, F ;
SINGH, PP ;
SRIVASTAVA, HC .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1986, 5 (03) :437-444
[10]   An alternative method for the selective bromination of alkylbenzenes using NaBrO3/NaHSO3 reagent [J].
Kikuchi, D ;
Sakaguchi, S ;
Ishii, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) :6023-6026