Large scale synthesis and regioselective protection schemes of ethyl 2-azido-2-deoxy-1-thio-α-D-cellobioside for preparation of heparin thiodisaccharide building blocks

被引:5
作者
Sheerin, Kevin [1 ]
Guazzelli, Lorenzo [1 ]
Oscarson, Stefan [1 ]
机构
[1] Univ Coll Dublin, Sch Chem, Dublin 4, Ireland
基金
爱尔兰科学基金会;
关键词
Heparin; Heparan sulfate; Azidonitration; Regioselective benzylation; Phase transfer brnzylation; CAPSULAR POLYSACCHARIDE; CHEMICAL-SYNTHESIS; MODULAR SYNTHESIS; PENTASACCHARIDE; GLUCOSE; BENZYLATION; DERIVATIVES; GLYCOSIDES; CELLOBIOSE; FRAGMENT;
D O I
10.1016/j.carres.2017.01.005
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
Crystalline acetylated ethyl 2-azido-2-deoxy-1-thio- alpha-D-cellobioside has been prepared on a multigram scale from cellobiose in an overall yield of 23% with no chromatography required and converted after deacetylation into the 4',6'-O-benzylidene and 4',6'-O-benzylidene-6-O-TBDMS protected derivatives. Applying a number of regioselective benzylation methods on these gave access to a variety of regioselectively protected derivatives, both mono-ols ( 2'-and 3-OH), diols ( 2',6-, 2',3-, and 3,6-di-OH), and triols ( 2',3,6-and 2',3',3-tri-OH). A number of these derivatives were further processed by benzoylation followed by removal or opening of the benzylidene acetal and selective oxidation of the exposed primary alcohol to give heparin building block intermediates comprising a range of possible sulfation patterns. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:16 / 31
页数:16
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