Carbohydrate Research p. 101 - 117 (1992)
Update date:2022-08-04
Topics:
Hronowski
Szarek
Hay
Krebs
Depew
1,2,3,2',3',4',6'-Hepta-O-acetyl-β-lactose (4) was coupled with 2,3,6,2',3',4',6'-hepta-O-acetyl-α-lactosyl bromide (7) in the presence of Hg(CN)2 to afford 1,2,3,2',3',4',6'-hepta-O-acetyl-6-O-(2,3,6,2',3',4',6'-hepta-O- acetyl-β-lactosyl)-β-lactose (11) which, upon O-deacetylation, gave 6-O-β-lactosyl-α,β-lactoses (64% from 4). In contrast, the reaction of 7 with benzyl 2,3,2',3',4',6'-hexa-O-acetyl-β-lactoside in the presence of Hg(CN)2 produced 3,6,2',3',4',6'-hexa-O-acetyl-1,2-O-(2,3,2',3',4',6'-hexa-O-acetyl-1- O-benzyl-β-lactos-6-yl orthoacetyl)-α-lactose (63%) and 3,6,2',3',4',6'-hexa-O-acetyl-1,2-O-(1-cyanoethylidene)-α-lactose (27%). The glycosidation of 4 using 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide in the presence of Hg(CN)2 afforded, after deprotection, 4,6-di-O-β-D-galactopyranosyl-α,β-D-glucoses (66%). The reaction of 11 with 1,2-di-O-benzyl-(R,S)-glycerols and trimethylsilyl trifluoromethanesulfonate yielded, after deprotection, 1-O-(6-O-β-lactosyl-β-lactosyl)-(R,S)-glycerols (18%). Under the same coupling conditions 11 reacted with 2-O-benzylglycerol to form 3-O-acetyl-2-O-benzyl-1-O-{2',3',4',6'-hexa-O-acetyl-6-O-(2,3,6,2',3' ,4',6'-hepta-O-acetyl-β-lactosyl)-β-lactosyl}-(R,S)-glycerols (16%). 1,2,3,2′,3′,4′,6′-Hepta-O-acetyl-β-lactose (4) was coupled with 2,3,6,2′,3′,4′,6′-hepta-O-Acetyl-α- lactosyl bromide (7) in the presence of Hg(CN)2 to afford 1,2,3,2′,3′,4′,6′-hepta-O-acetyl-6-O-(2,3,6,2′,3$ PRM, 4′,6′-hepta-O-acetyl-6-O-(2,3,6,2′,3′, 4′,-hepta-O-acetyl-β-lactosyl)-β-lactose (11) which, upon O-deacetylation, gave 6-O-β-lactosyl-α,β-lactoses (64% from 4). In contrast, the reaction of 7 with benzyl 2,3,2′,3′,4′,6′-hexa-O-acetyl-β-lactoside in the presence of Hg(CN)2 produced 3,6,2′,3′,4′,6′-hexa-O- acetyl-1,2-O-(2,3,2′,3′,4′,6′-hexa-O-acetyl-1-O-benzy l- β-lactos-6-yl orthoacctyl)-α-lactose (63%) and 3,6,2′,3′,4′,6′-hexa- O-acetyl-1,2-O-(1-cyanoethylidene)-α-lactose (27%). The glycosidation of 4 using 2,3,4,6-tetra-O-acetyl-α-D- galactoyranosyl bromide in the presence of Hg(CN)2 afforded, after deprotection, 4,6-di-O-β-D- galactopyranosyl-α,β-D-glucoses (66%). The reaction of 11 with 1,2-di-O-benzyl-(R,S)-glycerols and trimethylsilyl trifluoromethanesulfonate yielded, after deprotection, 1-O-(6-O-β-lactosyl-β-lactosyl)-(R,S)-glycerols (18%). Under the same coupling conditions II reacted with 2-O-benzylglycerol to form 3-O-acetyl-2-O-benzyl- O-{2′,3′,4′,6′-hexa-O-acetyl-6-O-(2,3,6,2′,3 ′, 4′,6′-hepta-O-acetyl-β-lactosyl)-β-lactosyl}-( R,S)- glycerols (16%).
View MorePengchen New Material Technology Co., Ltd.
Contact:+86-512-63680537
Address:99.6 km of national road 318, Meiyan Community,Pingwang Town, Wujiang District, Suzhou 215225
Suzhou BEC Fine Chemicals Co., Ltd.
website:http://www.bek.com.cn
Contact:0512-68095917 18913193865
Address:6, Jin Shan Road, Suzhou New District, 215011 China Suzhou Nations Pharmaceutical Innovation Center Inside
Wuhan Chemchemical Co., Ltd.(expird)
Contact:15973022782
Address:7-5-6218,Incubation Centre,Guandong Industry Park, East Lake High-Tech Development Zone,Wuhan City.
Contact:+86-021-6989-5597
Address:No.80 Yichuan Rd., Putuo District,Shanghai,P.R.China
Wuxi Innopal International Trade CO.,LTD
Contact:+86-510-80711901-8003
Address:Room 402,Building 5,Longze Garden,No.17,South huanjiu Road,Yixing City, Jiangsu,China
Doi:10.1021/acs.joc.9b02717
(2019)Doi:10.1021/ic50021a025
(1964)Doi:10.1016/j.tet.2010.07.007
(2010)Doi:10.1002/ejic.200600586
(2006)Doi:10.1021/jo00015a049
(1991)Doi:10.1021/ja806814c
(2009)