(2R,4S,5S)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-carboxylic acid methyl ester | 605669-69-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4S,5S)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,4S,5S)-4-hydroxy-5-(hydroxymethyl)oxolane-2-carboxylate
• CAS: 605669-69-0
• 化学式: C₇H₁₂O₅
• 分子量: 176.169
• InChiKey: CISQVXCSUSBQNY-JKUQZMGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4S,5S)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-carboxylic acid methyl ester 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 甲基磺酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,4R,5R)-4-Azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of all diastereomeric methyl 2,5-anhydro-3-deoxy-hexonates: precursors to C-2-deoxynucleosides and THF-templated γ- and δ-amino acids

  摘要：

  Efficient syntheses of all diastereomers of methyl 2,5-anhydro-3-deoxy-hexonate from mannono- or gulono-lactones provide precursors for C-nucleosides of 2-deoxyribose and for THF-templated gamma- and delta-amino acids. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01416-3
• 作为产物：
  描述：

  甲醇 、 3-deoxy-5,6-O-isopropylidene-2-O-mesyl-L-xylo-hexono-1,4-lactone 在 盐酸 作用下， 以66%的产率得到(2R,4S,5S)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of all diastereomeric methyl 2,5-anhydro-3-deoxy-hexonates: precursors to C-2-deoxynucleosides and THF-templated γ- and δ-amino acids

  摘要：

  Efficient syntheses of all diastereomers of methyl 2,5-anhydro-3-deoxy-hexonate from mannono- or gulono-lactones provide precursors for C-nucleosides of 2-deoxyribose and for THF-templated gamma- and delta-amino acids. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01416-3

文献信息

• Synthesis of all diastereomeric methyl 2,5-anhydro-3-deoxy-hexonates: precursors to C-2-deoxynucleosides and THF-templated γ- and δ-amino acids
  作者：Mark P. Watterson、Alison A. Edwards、John A. Leach、Martin D. Smith、Osamu Ichihara、George W.J. Fleet

  DOI：10.1016/s0040-4039(03)01416-3

  日期：2003.7

  Efficient syntheses of all diastereomers of methyl 2,5-anhydro-3-deoxy-hexonate from mannono- or gulono-lactones provide precursors for C-nucleosides of 2-deoxyribose and for THF-templated gamma- and delta-amino acids. (C) 2003 Elsevier Ltd. All rights reserved.