methyl 1(S)-carboxy-2(R),3(S)-<(dimethylmethylene)dioxy>-5(R)-hydroxy-4(R)-cyclopentanecarboxylate | 112576-29-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 1(S)-carboxy-2(R),3(S)-<(dimethylmethylene)dioxy>-5(R)-hydroxy-4(R)-cyclopentanecarboxylate
• 英文别名: methyl (+)-β-carboxy-7β-hydroxy-3,3-dimethyl-2,4-dioxabicyclo<3.3.0>octane-8β-carboxylate；(3aS,4R,5R,6S,6aR)-5-hydroxy-4-methoxycarbonyl-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxole-6-carboxylic acid
• CAS: 112576-29-1；112653-35-7
• 化学式: C₁₁H₁₆O₇
• 分子量: 260.244
• InChiKey: MXBLWWSZXKZEJF-WCMLQCRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.63
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  102.29
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 1(S)-carboxy-2(R),3(S)-<(dimethylmethylene)dioxy>-5(R)-hydroxy-4(R)-cyclopentanecarboxylate 在 吡啶 、 二乙胺基三氟化硫 、 [双(三氟乙酰氧基)碘]苯 作用下， 反应 6.67h， 生成 (3aR,4R,5R,6S,6aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-fluoro-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylamine
  参考文献：
  名称：

  Cotterill, Ian C.; Cox, Philip B.; Drake, Alex F., Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 3071 - 3076

  摘要：

  DOI：
• 作为产物：
  描述：

  (+/-)-4β-(methoxycarbonyl)-2α,3α-<(dimethylmethylene)dioxy>-5β-tert-butoxy-1β-cyclopentanecarboxylic acid 在 copper(II) sulfate 、 三氟乙酸 作用下， 以 丙酮 为溶剂， 反应 19.0h， 生成 methyl 1(S)-carboxy-2(R),3(S)-<(dimethylmethylene)dioxy>-5(R)-hydroxy-4(R)-cyclopentanecarboxylate
  参考文献：
  名称：

  Enantioselective hydrolysis of dimethyl 2.alpha.,3.alpha.-[(dimethylmethylene)dioxy]-5.beta.-hydroxy-1.beta.,4.beta.-cyclopentanedicarboxylate with pig liver esterase. Stereoselective synthesis of methyl 2(R),3(S)-[(dimethylmethylene)dioxy]-5(R)-hydroxy-1(S)-carboxy-4(R)-cyclopentanecarboxylate. A cyclopentane synthone with all ring atoms chiral

  摘要：

  DOI：

  10.1021/jo00240a002

文献信息

• ZEMLICKA, JIRI;CRAINE, LESLIE E.;HEEG, MARY-JANE;OLIVER, JOHN P., J. ORG. CHEM., 53,(1988) N 5, 937-942
  作者：ZEMLICKA, JIRI、CRAINE, LESLIE E.、HEEG, MARY-JANE、OLIVER, JOHN P.

  DOI：——

  日期：——
• Cotterill, Ian C.; Cox, Philip B.; Drake, Alex F., Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 3071 - 3076
  作者：Cotterill, Ian C.、Cox, Philip B.、Drake, Alex F.、Grand, Darren M. Le、Hutchinson, Edward J.、et al.

  DOI：——

  日期：——
• Enantioselective hydrolysis of dimethyl 2.alpha.,3.alpha.-[(dimethylmethylene)dioxy]-5.beta.-hydroxy-1.beta.,4.beta.-cyclopentanedicarboxylate with pig liver esterase. Stereoselective synthesis of methyl 2(R),3(S)-[(dimethylmethylene)dioxy]-5(R)-hydroxy-1(S)-carboxy-4(R)-cyclopentanecarboxylate. A cyclopentane synthone with all ring atoms chiral
  作者：Jiri Zemlicka、Leslie E. Craine、Mary Jane Heeg、John P. Oliver

  DOI：10.1021/jo00240a002

  日期：1988.3