1-deoxy-3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-α-D-psicofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-deoxy-3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-α-D-psicofuranose
• 英文别名: (3aR,4S,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2,4-trimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ol
• 化学式: C₂₅H₃₄O₅Si
• 分子量: 442.627
• InChiKey: OEMLCKYXCDMUNX-XAISMOLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-deoxy-3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-α-D-psicofuranose 在 sodium tetrahydroborate 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.25h， 生成 1-deoxy-3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-D-erythro-hexo-2,5-diulose
  参考文献：
  名称：

  Chiral 1,4-dicarbonyl-2,3-O-isopropylidene derivatives. Rapid racemization on standing

  摘要：

  1,4-Dicarbonyl-2,3-chiral derivatives are useful synthetic precursors for the preparation of carbocyclic rings but, in many cases, losses of optical purity have been reported, 1-Deoxy-3,4-O-isopropylidene-6-O-trityl-D-erythro-hexo-2,5-diulose and 1-deoxy-3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-D-erythro-hexo-2,5-diulose were synthesized from D-ribono-1,4-lactone. These compounds were selected to study the epimerizability of 2,3-O-isopropylidene-1,4-dicarbonyl derivatives. It was found that both compounds smoothly epimerize and partially racemize on standing. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00007-1
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 在 咪唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1-deoxy-3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-α-D-psicofuranose
  参考文献：
  名称：

  Chiral 1,4-dicarbonyl-2,3-O-isopropylidene derivatives. Rapid racemization on standing

  摘要：

  1,4-Dicarbonyl-2,3-chiral derivatives are useful synthetic precursors for the preparation of carbocyclic rings but, in many cases, losses of optical purity have been reported, 1-Deoxy-3,4-O-isopropylidene-6-O-trityl-D-erythro-hexo-2,5-diulose and 1-deoxy-3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-D-erythro-hexo-2,5-diulose were synthesized from D-ribono-1,4-lactone. These compounds were selected to study the epimerizability of 2,3-O-isopropylidene-1,4-dicarbonyl derivatives. It was found that both compounds smoothly epimerize and partially racemize on standing. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00007-1

文献信息

• Chiral 1,4-dicarbonyl-2,3-O-isopropylidene derivatives. Rapid racemization on standing
  作者：Juan B. Rodriguez

  DOI：10.1016/s0040-4020(99)00007-1

  日期：1999.2

  1,4-Dicarbonyl-2,3-chiral derivatives are useful synthetic precursors for the preparation of carbocyclic rings but, in many cases, losses of optical purity have been reported, 1-Deoxy-3,4-O-isopropylidene-6-O-trityl-D-erythro-hexo-2,5-diulose and 1-deoxy-3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-D-erythro-hexo-2,5-diulose were synthesized from D-ribono-1,4-lactone. These compounds were selected to study the epimerizability of 2,3-O-isopropylidene-1,4-dicarbonyl derivatives. It was found that both compounds smoothly epimerize and partially racemize on standing. (C) 1999 Elsevier Science Ltd. All rights reserved.