Carbohydrate research p. 77 - 85 (1988)
Update date:2022-08-02
Topics:
Thomas
Abbas
Matta
Benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside was converted into its 4-O-(methylsulfonyl) derivative (2) by treatment with methanesulfonyl chloride in pyridine. Displacement of the methylsulfonyloxy group of 2 with fluoride ion afforded benzyl 2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-4-fluoro-alpha-D-galactopyranosi de, which on hydrogenolysis, followed by acetylation, furnished 2-acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-galactopyranose. Treatment of this and of 2-acetamido-1,3,4-tri-O-acetyl-2,6-dideoxy-6-fluoro-D-glucopyranose with trimethylsilyl trifluoromethanesulfonate in 1,2-dichloroethane at approximately 50 degrees afforded the 4-deoxy-4-fluoro- or the 6-deoxy-6-fluoro-oxazolines (5) and (11), respectively. Reaction of 5 and 11 with dibenzyl phosphate in 1,2-dichloroethane produced the alpha-linked dibenzyl phosphate derivatives 6 and 12, respectively. Catalytic hydrogenation of 6 provided 2-acetamido-3,6-di-O-acetyl-2,4-dideoxy-4-fluoro-alpha-D-galactopyranosy l phosphate (7), and that of 12 gave 2-acetamido-3,4-di-O-acetyl-2,6-dideoxy-6-fluoro-alpha-D-glucopyranosyl phosphate (13). Coupling of 7 and 13 with uridine 5'-monophosphomorpholidate in dry pyridine at approximately 37 degrees, followed by O-deacetylation, furnished the title compounds, respectively, isolated and characterized as their respective dilithium salts.
View MoreFUJIAN SHANSHUI CHEMICAL CORP.LTD.
Contact:+86-151-59920036
Address:Jinqiao Gareden, jo@fj-xinyi.com
Contact:86 513 85512619
Address:Rm.1306, Building A, Wenfeng Mansion,168 Gongnong Road, Nantong Jiangsu China
Contact:--
Address:80G, No.1 Building, Guodu Development Mansion, No. 182 Zhaohui Road, Hangzhou City, Zhejiang Province,China.
Lanzhou huibang biological chemical technology Co., LTD
Contact:0931-7843964
Address:NO.2011,Yannan Road,Chengguan,
Hunan Shineway Enterprise Co., Ltd.
Contact:+86-731-86303875
Address:118, Huanghua International Airport Road, Huanghua Town, Changsha, Hunan 410137, China
Doi:10.1246/cl.1988.1837
(1988)Doi:10.1021/ic9020542
(2010)Doi:10.1021/ol902545q
(2010)Doi:10.1016/j.tetlet.2009.11.002
(2010)Doi:10.1080/15421400903065705
(2009)Doi:10.1021/tx900402x
(2010)