ENZYMATIC ESTERIFICATION AND DE-ESTERIFICATION OF CARBOHYDRATES - SYNTHESIS OF A NATURALLY-OCCURRING RHAMNOPYRANOSIDE OF P-HYDROXYBENZALDEHYDE AND A SYSTEMATIC INVESTIGATION OF LIPASE-CATALYZED ACYLATION OF SELECTED ARYLPYRANOSIDES

被引：51
作者：
BASHIR, NB [1 ]
PHYTHIAN, SJ [1 ]
REASON, AJ [1 ]
ROBERTS, SM [1 ]
机构：
[1] WELLCOME FDN LTD,DARTFORD DA1 5AH,KENT,ENGLAND
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 18期
关键词：
D O I：
10.1039/p19950002203
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The regiocontrolled esterification and de-esterification of mono- and di-saccharides is reviewed. New results involving the enzyme-catalysed regioselective acylation of ribo-110, arabino-112, 119, xylo-111, and rhamnopyranosides 116, 118 (as well as two arylpyranosides 125 and 136), are reported. This methodology is then applied to the total synthesis of the naturally occurring rhamnopyranoside 4-(4-O-acetyl-alpha-L-rhamnosyloxy)benzaldehyde 122.
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页码：2203 / 2222
页数：20
相关论文
共 51 条
  • [1] ENZYME CATALYZED PREPARATION OF 6-O-ACYLGLUCOPYRANOSIDES
    ADELHORST, K
    BJORKLING, F
    GODTFREDSEN, SE
    KIRK, O
    [J]. SYNTHESIS-STUTTGART, 1990, (02): : 112 - 115
  • [2] REGIOSELECTIVE DEACYLATION OF 1,6-ANHYDRO-BETA-D-GALACTOPYRANOSE DERIVATIVES CATALYZED BY SOLUBLE AND IMMOBILIZED LIPASES
    BALLESTEROS, A
    BERNABE, M
    CRUZADO, C
    MARTINLOMAS, M
    OTERO, C
    [J]. TETRAHEDRON, 1989, 45 (22) : 7077 - 7082
  • [3] SYNTHESIS OF 4-OBETA-D-GLUCOPYRANOSYL-L-RHAMNOPYRANOSE
    BEBAULT, GM
    DUTTON, GGS
    [J]. CANADIAN JOURNAL OF CHEMISTRY, 1972, 50 (20): : 3373 - &
  • [4] A HIGHLY SELECTIVE ENZYME-CATALYZED ESTERIFICATION OF SIMPLE GLUCOSIDES
    BJORKLING, F
    GODTFREDSEN, SE
    KIRK, O
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (14) : 934 - 935
  • [5] BOLAND W, 1991, SYNTHESIS-STUTTGART, P1049
  • [6] APPLICATION OF PROTEASE-CATALYZED REGIOSELECTIVE ESTERIFICATION IN SYNTHESIS OF 6'-DEOXY-6'-FLUOROLACTOSIDE AND 6-DEOXY-6-FLUOROLACTOSIDE
    CAI, SP
    HAKOMORI, S
    TOYOKUNI, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) : 3431 - 3437
  • [7] ENZYMATIC-SYNTHESIS OF VARIOUS 1'-O-SUCROSE AND 1-O-FRUCTOSE ESTERS
    CARREA, G
    RIVA, S
    SECUNDO, F
    DANIELI, B
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (05): : 1057 - 1061
  • [8] REGIOSELECTIVE ENZYMATIC DEACETYLATION OF OCTA-O-ACETYLSUCROSE - PREPARATION OF HEPTA-O-ACETYLSUCROSES
    CHANG, KY
    WU, SH
    WANG, KT
    [J]. CARBOHYDRATE RESEARCH, 1991, 222 : 121 - 129
  • [9] REGIOSELECTIVE ENZYMATIC ACETYLATION OF METHYL 4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE AND 4,6-O-BENZYLIDENE-BETA-D-GLUCOPYRANOSIDE
    CHINN, MJ
    LACAZIO, G
    SPACKMAN, DG
    TURNER, NJ
    ROBERTS, SM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (06): : 661 - 662
  • [10] REGIOSELECTIVE ACYLATION OF 1,6-ANHYDRO-BETA-D-GLUCOPYRANOSE CATALYZED BY LIPASES
    CHON, C
    HEISLER, A
    JUNOT, N
    LEVAYER, F
    RABILLER, C
    [J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (12) : 2441 - 2444
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