2,4-di-O-benzyl-3,6-dideoxy-α-D-ribo-hexopyranosyl chloride | 82086-31-5

• 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: 2,4-di-O-benzyl-3,6-dideoxy-α-D-ribo-hexopyranosyl chloride
• 英文别名: (2R,3R,5S,6R)-2-chloro-6-methyl-3,5-bis(phenylmethoxy)oxane
• CAS: 82086-31-5
• 化学式: C₂₀H₂₃ClO₃
• 分子量: 346.854
• InChiKey: FRDGAGFAROGXCC-NMLACTOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,4-di-O-benzyl-3,6-dideoxy-α-D-ribo-hexopyranosyl chloride 在 palladium on activated charcoal 氢气 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 生成 8-methoxycarbonyloctyl 3-O-(3,6-dideoxy-α-D-ribo-hexopyranosyl)-2-O-α-D-galactopyranosyl-α-D-mannopyranoside
  参考文献：
  名称：

  Antigenic determinants of Salmonella serogroups A and D1.Synthesis of trisaccharide glycosides for use as artificial antigens

  摘要：

  The disaccharide glycoside 8-methoxycarbonyloctyl 4,6-O-cyclohexylidine-2-O-(tetra-O-benzyl-alpha-D-galactopyranosyl)-alpha-D-manno pyranoside (7) was used as a common intermediate to the trisaccharide determinants of both Salmonella serogroups A and D1. Acetalation of 8-methoxycarbonyloctyl alpha-D-mannopyranoside provided the 4,6-acetal derivative, which was selectively benzoylated to give the partially protected mannoside 4. Reaction of 4 with tetra-O-benzyl-alpha-D-galacto-pyranosyl chloride afforded the fully protected disaccharide, which, after transesterification, gave the selectively blocked, disaccharide glycoside (7). Addition of tyvelose by way of its 2,4-di-O-benzoyl-3,6-dideoxy-alpha-D-arabino-hexopyranosyl chloride derivative gave the blocked trisacchride determinant of Salmonella serogroup D1. 2,4,-Di-O-benzyl-3,6-dideoxy-alpha-D-ribo-hexopyranosyl chloride reacted with 7 to provide, after removal of blocking groups, the paratose-containing determinant of serogroup A.

  DOI：

  10.1016/s0008-6215(82)80005-0
• 作为产物：
  描述：

  methyl 3,6-dideoxy-β-D-ribo-hexopyranoside 在 sodium hydride 、 zinc(II) chloride 作用下， 以 not given 为溶剂， 反应 19.5h， 生成 2,4-di-O-benzyl-3,6-dideoxy-α-D-ribo-hexopyranosyl chloride
  参考文献：
  名称：

  Antigenic determinants of Salmonella serogroups A and D1.Synthesis of trisaccharide glycosides for use as artificial antigens

  摘要：

  The disaccharide glycoside 8-methoxycarbonyloctyl 4,6-O-cyclohexylidine-2-O-(tetra-O-benzyl-alpha-D-galactopyranosyl)-alpha-D-manno pyranoside (7) was used as a common intermediate to the trisaccharide determinants of both Salmonella serogroups A and D1. Acetalation of 8-methoxycarbonyloctyl alpha-D-mannopyranoside provided the 4,6-acetal derivative, which was selectively benzoylated to give the partially protected mannoside 4. Reaction of 4 with tetra-O-benzyl-alpha-D-galacto-pyranosyl chloride afforded the fully protected disaccharide, which, after transesterification, gave the selectively blocked, disaccharide glycoside (7). Addition of tyvelose by way of its 2,4-di-O-benzoyl-3,6-dideoxy-alpha-D-arabino-hexopyranosyl chloride derivative gave the blocked trisacchride determinant of Salmonella serogroup D1. 2,4,-Di-O-benzyl-3,6-dideoxy-alpha-D-ribo-hexopyranosyl chloride reacted with 7 to provide, after removal of blocking groups, the paratose-containing determinant of serogroup A.

  DOI：

  10.1016/s0008-6215(82)80005-0

文献信息

• Bock, Klaus; Meldal, Morten, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1984, vol. 38, # 3, p. 255 - 266
  作者：Bock, Klaus、Meldal, Morten

  DOI：——

  日期：——
• Antigenic determinants of Salmonella serogroups A and D1.Synthesis of trisaccharide glycosides for use as artificial antigens
  作者：Tommy Iversen、David R. Bundle

  DOI：10.1016/s0008-6215(82)80005-0

  日期：1982.5

  The disaccharide glycoside 8-methoxycarbonyloctyl 4,6-O-cyclohexylidine-2-O-(tetra-O-benzyl-alpha-D-galactopyranosyl)-alpha-D-manno pyranoside (7) was used as a common intermediate to the trisaccharide determinants of both Salmonella serogroups A and D1. Acetalation of 8-methoxycarbonyloctyl alpha-D-mannopyranoside provided the 4,6-acetal derivative, which was selectively benzoylated to give the partially protected mannoside 4. Reaction of 4 with tetra-O-benzyl-alpha-D-galacto-pyranosyl chloride afforded the fully protected disaccharide, which, after transesterification, gave the selectively blocked, disaccharide glycoside (7). Addition of tyvelose by way of its 2,4-di-O-benzoyl-3,6-dideoxy-alpha-D-arabino-hexopyranosyl chloride derivative gave the blocked trisacchride determinant of Salmonella serogroup D1. 2,4,-Di-O-benzyl-3,6-dideoxy-alpha-D-ribo-hexopyranosyl chloride reacted with 7 to provide, after removal of blocking groups, the paratose-containing determinant of serogroup A.