ethyl O-(2-O-benzyl-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-(1->3)-O-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside | 953079-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl O-(2-O-benzyl-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-(1->3)-O-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside
• CAS: 953079-83-9
• 化学式: C₆₁H₇₀O₁₇S
• 分子量: 1107.28
• InChiKey: LUAYTKGCCYJBNR-JGYCTHIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.59
• 重原子数：
  79.0
• 可旋转键数：
  23.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  180.43
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  ethyl O-(2-O-benzyl-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-(1->3)-O-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 、 1,2,4,5-tetra-O-benzyl-D/L-ribitol 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.17h， 以70%的产率得到O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->3)-O-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-1,2,4,5-tetra-O-benzyl-D/L-ribitol
  参考文献：
  名称：

  Efficient stereoselective synthesis of oligosaccharides of Streptococcus pneumoniae serotypes 6A and 6B containing multiple 1,2-cis glycosidic linkages

  摘要：

  The synthesis of the repeating units of pneumococcal polysaccharide serotypes 6A and 6B and derivatives thereof is described. Application of S-benzoxazolyl and S-thiazolinyl glycosides allowed rapid oligosaccharide assembly and provided complete stereoselectivity in challenging 1,2-cis glucosylations and galactosylations. The oligosaccharide assembly was accomplished in an efficient manner by selective activation of thioimidoyl leaving groups over thioglycosides. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.036
• 作为产物：
  描述：

  ethyl 2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 在 3 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 15.5h， 生成 ethyl O-(2-O-benzyl-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-(1->3)-O-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  Efficient stereoselective synthesis of oligosaccharides of Streptococcus pneumoniae serotypes 6A and 6B containing multiple 1,2-cis glycosidic linkages

  摘要：

  The synthesis of the repeating units of pneumococcal polysaccharide serotypes 6A and 6B and derivatives thereof is described. Application of S-benzoxazolyl and S-thiazolinyl glycosides allowed rapid oligosaccharide assembly and provided complete stereoselectivity in challenging 1,2-cis glucosylations and galactosylations. The oligosaccharide assembly was accomplished in an efficient manner by selective activation of thioimidoyl leaving groups over thioglycosides. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.036