2,2-Dimethyl-propionic acid (2S,3S,4R,5R)-2-((R)-1,2-dihydroxy-ethyl)-4-(2,2-dimethyl-propionyloxy)-5-methoxy-tetrahydro-furan-3-yl ester | 213475-90-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2-Dimethyl-propionic acid (2S,3S,4R,5R)-2-((R)-1,2-dihydroxy-ethyl)-4-(2,2-dimethyl-propionyloxy)-5-methoxy-tetrahydro-furan-3-yl ester
• CAS: 213475-90-2
• 化学式: C₁₇H₃₀O₈
• 分子量: 362.42
• InChiKey: YQKNJQKIOVWFSQ-KSSYENDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  111.52
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (2S,3S,4R,5R)-2-((R)-1,2-dihydroxy-ethyl)-4-(2,2-dimethyl-propionyloxy)-5-methoxy-tetrahydro-furan-3-yl ester 在 1,1-二氯甲醚 、 sodium methylate 、 四氯化锡 、 四丁基碘化铵 、 sodium hydride 、 硫脲 作用下， 以 吡啶 、 甲醇 、 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 (1S,3R,5R,7R,8S,9R)-8-Benzyloxy-9-benzyloxymethyl-5-tert-butyl-2,4,6,10-tetraoxa-tricyclo[3.3.2.0^3,7]decane
  参考文献：
  名称：

  A novel synthetic method for α-d-galactofuranose 1,2,5-orthopivalate

  摘要：

  In order to synthesize (1-->5)-beta-D-galactofuranan by rig-opening polymerization, 3,6-di-O-benzyl-alpha-D-galactofuranose 1,2,5-orthopivalate (9) the most appropriate monomer was synthesized from D-galactose via 10 reaction steps. Novel intramolecular orthoesterification, which is a key reaction for sythesizing compound 9, was accomplished by treatment of 5-O-monocholoacetyl-2,3,6-tri-O-pivaloyl-D-galactofuranosyl chloride (6) with thiourea in pyridine at 80 degrees C to give the expected orthoester (7) in good yield without any side reactions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00120-7
• 作为产物：
  描述：

  2,2-Dimethyl-propionic acid (2S,3S,4R,5R)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-(2,2-dimethyl-propionyloxy)-5-methoxy-tetrahydro-furan-3-yl ester 以 水 、 溶剂黄146 为溶剂， 反应 0.75h， 以96.5%的产率得到2,2-Dimethyl-propionic acid (2S,3S,4R,5R)-2-((R)-1,2-dihydroxy-ethyl)-4-(2,2-dimethyl-propionyloxy)-5-methoxy-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  A novel synthetic method for α-d-galactofuranose 1,2,5-orthopivalate

  摘要：

  In order to synthesize (1-->5)-beta-D-galactofuranan by rig-opening polymerization, 3,6-di-O-benzyl-alpha-D-galactofuranose 1,2,5-orthopivalate (9) the most appropriate monomer was synthesized from D-galactose via 10 reaction steps. Novel intramolecular orthoesterification, which is a key reaction for sythesizing compound 9, was accomplished by treatment of 5-O-monocholoacetyl-2,3,6-tri-O-pivaloyl-D-galactofuranosyl chloride (6) with thiourea in pyridine at 80 degrees C to give the expected orthoester (7) in good yield without any side reactions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00120-7