SYNTHESIS OF TRIDEUTERIOMETHYL 5-DEUTERIUM-BETA-D-MANNOPYRANOSIDE

被引:2
作者
GODDAT, J
DATTA, P
GREY, AA
CARVER, JP
SHAH, RN
机构
[1] UNIV TORONTO,DEPT MOLEC & MED GENET,TORONTO M5S 1A8,ONTARIO,CANADA
[2] UNIV TORONTO,CARBOHYDRATE RES CTR,TORONTO M5S 1A8,ONTARIO,CANADA
基金
英国医学研究理事会;
关键词
D O I
10.1080/07328309308019008
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The title compound was prepared by first converting trideuteriomethyl 2,3,4-tri-O-benzyl-beta-D-mannopyranoside to a 6-bromo-6-deoxy derivative which on elimination by using DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) or DBN (1,5-diazabicyclo[4.3.0]non-5-ene) gave a hex-5-enopyranoside derivative. The deuteroboration of the hex-5-enopyranoside followed by oxidation and subsequent deblocking produced trideuteriomethyl 5-deuterium-beta-D-mannopyranoside.
引用
收藏
页码:793 / 800
页数:8
相关论文
共 9 条
[1]   CARBOCYCLIC COMPOUNDS FROM MONOSACCHARIDES .2. TRANSFORMATIONS IN THE MANNOSE SERIES [J].
BERNET, B ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1979, 62 (07) :2400-2410
[2]  
Blair M. G., 1963, METHODS CARBOHYDRATE, V2, P415
[3]  
BROWN HC, 1983, CURRENT TRENDS ORGAN, P247
[4]  
DIME DS, 1987, J LABELL COMP RADIOP, V6, P725
[5]   ALKYLMETAL ASYMMETRIC REDUCTION .20. A REINVESTIGATION ON THE STEREOCHEMISTRY OF KETONE REDUCTIONS BY OPTICALLY-ACTIVE ALKYLMETAL COMPOUNDS [J].
FALORNI, M ;
LARDICCI, L ;
GIACOMELLI, G .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) :2383-2388
[6]   SELECTIVE HYDROBORATION STUDIES WITH ACETOXYBOROHYDRIDE [J].
GAUTAM, VK ;
SINGH, J ;
DHILLON, RS .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (01) :187-189
[7]   ACCESSIBILITY OF D-MANNOPYRANOSIDE GLYCOSYLATING SYNTHONS BY ACETOLYSIS FOR PREPARATIONS OF OLIGOSACCHARIDE MOIETIES OF N-LINKED GLYCOPROTEINS [J].
SHAH, RN ;
BAPTISTA, J ;
PERDOMO, GR ;
CARVER, JP ;
KREPINSKY, JJ .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1987, 6 (04) :645-660
[8]   SYNTHESES OF MODEL OLIGOSACCHARIDES OF BIOLOGICAL SIGNIFICANCE .5. SYNTHESIS OF A TETRASACCHARIDE OF THE EXTENDED CORE-REGION OF THE SACCHARIDE MOIETY OF N-LINKED GLYCOPROTEINS [J].
SHAH, RN ;
CUMMING, DA ;
GREY, AA ;
CARVER, JP ;
KREPINSKY, JJ .
CARBOHYDRATE RESEARCH, 1986, 153 (01) :155-161
[9]  
SHAH RN, 1990, 15TH INT S CARB CHEM