1,2,3,5-tetra-O-benzyl-D-ribitol | 953079-76-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2,3,5-tetra-O-benzyl-D-ribitol
• 英文别名: (2R,3R,4S)-1,3,4,5-tetrakis(phenylmethoxy)pentan-2-ol
• CAS: 953079-76-0
• 化学式: C₃₃H₃₆O₅
• 分子量: 512.646
• InChiKey: LOOIEFVXBXAXKR-XKKJXBDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2,3,5-tetra-O-benzyl-D-ribitol 在 palladium on activated charcoal N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 30.17h， 生成 O-(α-L-rhamnopyranosyl)-(1->4)-D-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：

  2,3,5-三-O-(苯基甲基)-D-呋喃核糖 在 sodium hydroxide 、 sodium tetrahydroborate 、 四丁基溴化铵 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 16.25h， 生成 1,2,3,5-tetra-O-benzyl-D-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

文献信息

• Efficient stereoselective synthesis of oligosaccharides of Streptococcus pneumoniae serotypes 6A and 6B containing multiple 1,2-cis glycosidic linkages
  作者：Archana R. Parameswar、Papapida Pornsuriyasak、Nicole A. Lubanowski、Alexei V. Demchenko

  DOI：10.1016/j.tet.2007.07.036

  日期：2007.10

  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.