Journal of the Chemical Society. Perkin transactions I p. 1165 - 1170 (1987)
Update date:2022-08-04
Topics:
Gigg, Jill
Gigg, Roy
Payne, Sheila
Conant, Robert
Epoxidation of allyl 4-O-(2,4-di-O-benzyl-3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranoside and subsequent alkaline hydrolysis of the epoxide and hydrogenolysis of the benzyl groups gave 2',3'-dihydroxypropyl 2,3-di-O-methyl-4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside which was cleaved with sodium metaperiodate to give the corresponding formylmethyl glycoside.Two other routes to the latter compound, via allyl 2,3-di-O-methyl-4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside, were also developed.The formylmethyl glycoside was coupled to bovine serum albumin using 'reductive amination' in the presence of sodium cyanoborohydride to give a glycoconjugate useful for the serodiagnosis of antibodies to the major glycolipid of Mycobacterium leprae in the sera of leprosy patients. 5',6'-Dihydroxyhexyl and 10',11'-dihydroxyundecyl 3,6-di-O-methyl-β-D-glucopyranosides were also prepared as intermediates for the synthesis of the 4-formylbutyl and 9-formylnonyl glucosides respectively which are also suitable for coupling to bovine serum albumin by the 'reductive amination' technique.
View MoreContact:+86-371-55981030
Address:Room 1571, Macalline Soho, No.1, Shangdu Road, Zhengzhou, Henan
website:http://www.np-chem.com
Contact:0086-25-52346877
Address:199, Jian Ye Road, Nanjing, China
ShangHai Soyoung Biotechnology Inc
website:http://www.soyoungbio.com
Contact:+86-21-69893009
Address:shanghai
wuxi huabin bio-tech Co.,Ltd(expird)
Contact:86-0510-85133006
Address:hubin road NO157
Heliosense Biotechnologies, Inc.
website:https://www.heliosense.com/
Contact:+86-592-5667290
Address:Xiamen Torch Hi-tech Zone Venture Weiye Building S506
Doi:10.1016/j.bmcl.2008.11.007
(2009)Doi:10.1246/bcsj.44.3028
(1971)Doi:10.1002/chem.200802066
(2009)Doi:10.1039/c39940000719
(1994)Doi:10.1039/c39890000754
(1989)Doi:10.1139/v60-160
(1960)
