S-benzoxazolyl (SBox) glycosides in oligosaccharide synthesis:: Novel glycosylation approach to the synthesis of β-D-glucosides, β-D-galactosides, and α-D-mannosides
S-benzoxazolyl (SBox) glycosides in oligosaccharide synthesis:: Novel glycosylation approach to the synthesis of β-D-glucosides, β-D-galactosides, and α-D-mannosides
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DOI：
10.1055/s-2003-40345
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发表时间：
2003-01-01
期刊：
影响因子：
2
通讯作者：
De Meo, C
中科院分区：
文献类型：
--
作者：
Demchenko, AV;Kamat, MN;De Meo, C
合成了乙酰化和苯甲酰化的s -苯并恶唑（SBox）糖苷，并将其应用于高效的1,2-反式糖基化。合成β - d -糖苷、β - d -半乳糖苷和α - d -甘露糖苷具有完全的立体选择性和显著的高收率。研究还表明，苯甲酰化的“解除武装”SBox糖苷在解除武装和解除武装的乙基硫甙存在下都可以选择性地活化。四糖β - d - glc -(1-6)- β - d - gal -(1-6)- β - d - glcnac -(1-6)- α - d - glcome通过三个连续的选择性糖基化步骤聚合合成。
Per-acetylated and per-benzoylated S-benzoxazolyl (SBox) glycosides have been synthesized and applied to highly efficient 1,2-trans glycosylation. Complete stereoselectivities and remarkably high yields were achieved for the synthesis of beta-D-glucosides, beta-D-galactosides, and alpha-D-mannosides. It was also demonstrated that benzoylated 'disarmed' SBox glycosides could be selectively activated in the presence of both armed and disarmed ethyl thioglycosides. Convergent synthesis of the tetrasaccharide beta-D-Glc-(1-6)-beta-D-Gal-(1-6)-beta-D-GlcNAc-(1-6)-alpha-D-GlcOMe was achieved in three sequential selective glycosylation steps.