methyl 3,6-dideoxy-β-D-ribo-hexopyranoside | 31505-15-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,6-dideoxy-β-D-ribo-hexopyranoside
• 英文别名: methyl 3,6-dideoxy-β-D-xylo-hexopyranoside；3,6-dideoxy-β-D-ribo-hexopyranoside；Methyl-3,6-didesoxy-β-D-ribo-hexopyranosid；(2R,3R,5S,6R)-2-methoxy-6-methyloxane-3,5-diol
• CAS: 31505-15-4
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: DRIBCYZSKHETPK-XZBKPIIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3,6-dideoxy-β-D-ribo-hexopyranoside 在 silver trifluoromethanesulfonate 、 sodium hydride 、 1,1,3,3-四甲基脲 、 zinc(II) chloride 作用下， 以 乙腈 为溶剂， 反应 19.5h， 生成 8-methoxycarbonyloctyl 4,6-O-cyclohexylidene-3-O-(2,4-di-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-2-O-(tetra-O-benzyl-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：

  甲基 Β-D-吡喃葡萄糖苷 在 palladium on activated charcoal 吡啶 、 六甲基磷酰三胺 、 N-溴代丁二酰亚胺(NBS) 、 水 、 氢气 、 sodium methylate 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 68.58h， 生成 methyl 3,6-dideoxy-β-D-ribo-hexopyranoside
  参考文献：
  名称：

  Synthesis of methyl 2,6-dideoxy-β-D-arabino-, 3,6-dideoxy-β-D-ribo-, and 4,6-dideoxy-β-D-xylo-hexopyranosides

  摘要：

  DOI：

  10.1007/bf00629918

文献信息

• 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.
• Synthesis of methyl 2,6-dideoxy-β-D-arabino-, 3,6-dideoxy-β-D-ribo-, and 4,6-dideoxy-β-D-xylo-hexopyranosides
  作者：E. V. Evtushenko

  DOI：10.1007/bf00629918

  日期：1991.11