Methyl 2,4-dideoxy-D-erythro-hexopyranoside | 139342-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: Methyl 2,4-dideoxy-D-erythro-hexopyranoside
• 英文别名: Methyl-2,4-dideoxy-D-erythro-hexapyranoside；(2S,4R)-2-(hydroxymethyl)-6-methoxyoxan-4-ol
• CAS: 139342-81-7
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: KXNRAPQYUAQAFX-JEAXJGTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  2
• 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 2,4-dideoxy-D-erythro-hexopyranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 氨 、 溶剂黄146 、 牛血清白蛋白 作用下， 以 甲醇 为溶剂， 反应 87.25h， 生成 1-(2,4-dideoxy-α-D-erythro-hexopyranosyl)thymine
  参考文献：
  名称：

  Synthesis of 2,4-dideoxy-.beta.-D-erythro-hexopyranosyl nucleosides

  摘要：

  The synthesis of 1-(2,4-dideoxy-beta-D-erythro-hexopyranosyl)thymine (12)1 was accomplished using two different synthetic routes. It was obtained starting either from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose or from tri-O-acetyl-D-glucal. The other modified nucleosides, with either a cytosine, guanine, or adenine moiety, were synthesized using the second reaction scheme. Deoxygenation reactions were accomplished with the (2,4-dichlorophenoxy)thiocarbonyl derivatives generated in situ.

  DOI：

  10.1021/jo00063a013
• 作为产物：
  描述：

  (3R,5S)-5-Acetoxy-3-<(tert-butyldimethylsilyl)oxy>-6-hydroxyhexanal 在 Dowex-H⁽¹⁺⁾ 作用下， 以 甲醇 为溶剂， 以75%的产率得到Methyl 2,4-dideoxy-D-erythro-hexopyranoside
  参考文献：
  名称：

  Enantioselective synthesis of all 2,4-dideoxyhexose stereoisomers

  摘要：

  The preparation of all possible methyl 2,4-dideoxyhexopyranosides starting from optically pure enzymatic asymmetrization products 1 and 2 is reported.

  DOI：

  10.1016/0040-4039(91)80592-t

文献信息

• Enantio- and diastereoselective transformations of cycloheptatriene to sugars and related products
  作者：Carl R. Johnson、Adam Golebiowski、Darryl H. Steensma、Mark A. Scialdone

  DOI：10.1021/jo00077a049

  日期：1993.12

  Both meso diastereomers of 6-[(tert-butyldimethylsilyl)oxy]-2-cycloheptene-1,4-diol, prepared from cycloheptatriene, have been enzymatically asymmetrized by conversion to monoacetates using Pseudomonas cepacia lipase in isopropenyl acetate. A study of protecting group manipulations, diastereoselective oxidations, and regioselective ring openings utilizing these enantiopure monacetates which results in the synthesis of all possible methyl 2,4-dideoxyhexopyranosides is described.