2,3-O-isopropylidene-3-C-methyl-D-erythrono-1,4-lactone | 274257-77-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-isopropylidene-3-C-methyl-D-erythrono-1,4-lactone
• 英文别名: (3aR,6aR)-2,2,3a-trimethyl-4,6a-dihydrofuro[3,4-d][1,3]dioxol-6-one
• CAS: 274257-77-1
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: PWIMWAFHIYTCCN-YLWLKBPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-O-isopropylidene-3-C-methyl-D-erythrono-1,4-lactone 、 甲基溴化镁 以 四氢呋喃 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  Doubly carbon-branched pentoses: synthesis of both enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection

  摘要：

  An acetonide is the only protecting group used in the synthesis of both the enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose via the enantiomeric 3-C-methyl-L-erythronolactone [from 2-C-methyl-D-ribono-lactone or D-ribose] and 3-C-methyl-D-erythronolactone [from D-tagatose Or L-ribose]. NMR studies on unprotected C-methyl arabinoses show that methyl branching significantly affects the ratios of pyranose and furanose forms present in aqueous Solution. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.098
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 生成 2,3-O-isopropylidene-3-C-methyl-D-erythrono-1,4-lactone
  参考文献：
  名称：

  Doubly carbon-branched pentoses: synthesis of both enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection

  摘要：

  An acetonide is the only protecting group used in the synthesis of both the enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose via the enantiomeric 3-C-methyl-L-erythronolactone [from 2-C-methyl-D-ribono-lactone or D-ribose] and 3-C-methyl-D-erythronolactone [from D-tagatose Or L-ribose]. NMR studies on unprotected C-methyl arabinoses show that methyl branching significantly affects the ratios of pyranose and furanose forms present in aqueous Solution. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.098

文献信息

• BARRETT, ANTHONY G. M.;BEZUIDENHOUDT, BAREND C. B.;DHANAK, DASHYANT;GASIE+, J. ORG. CHEM., 54,(1989) N4, C. 3321-3324
  作者：BARRETT, ANTHONY G. M.、BEZUIDENHOUDT, BAREND C. B.、DHANAK, DASHYANT、GASIE+

  DOI：——

  日期：——
• BARRETT, ANTHONY G. M.;DHANAK, DASHYANT, TETRAHEDRON LETT., 28,(1987) N 29, 3327-3330
  作者：BARRETT, ANTHONY G. M.、DHANAK, DASHYANT

  DOI：——

  日期：——