6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-altrono-1,5-lactone | 137126-35-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-altrono-1,5-lactone
• 英文别名: (3aR,4R,7S,7aS)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one
• CAS: 137126-35-3
• 化学式: C₁₅H₂₈O₆Si
• 分子量: 332.469
• InChiKey: HUZWIRLJMBLANG-KXNHARMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-altrono-1,5-lactone 在 吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.34h， 生成 methyl (3aR,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate
  参考文献：
  名称：

  由糖内酯合成四氢吡喃

  摘要：

  γ-和δ-己内酯的脱水，可以通过在C-2处的三氟甲磺酸酯离去基团的分子内亲核置换，或通过OH-6的Mitsunobu型置换来实现，可以得到含有四氢吡喃环的双环内酯。这些双环内酯的还原或亲核开环以良好的产率提供了多官能化的四氢吡喃。

  DOI：

  10.1016/s0040-4020(98)00837-0
• 作为产物：
  描述：

  2,3-异亚丙氧基-D-呋喃核糖苷 在 咪唑 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-altrono-1,5-lactone
  参考文献：
  名称：

  Acetonides of α-hydroxy-δ-altronolactones

  摘要：

  The preparation and characterisation of some derivatives of alpha-hydroxy-delta-lactones, in which the delta-carbon substituent on the lactone ring is trans to an adjacent isopropylidene protected diol, are described; the X-ray crystal structures of 3,4-O-isopropylidene-D-altrono-1,5-lactone and of 3,4:6,7-di-O-isopropylidene-D-glycero-D-altro-heptono-1,5-lactone are reported.

  DOI：

  10.1016/s0957-4166(00)82202-8

文献信息

• Tetrahydropyran derivatives from γ- and δ-hexonolactones
  作者：Juan C. Estevez、Antony J. Fairbanks、Kenneth Y. Hsia、Peter Ward、George W.J. Fleet

  DOI：10.1016/s0040-4039(00)76908-5

  日期：1994.5

  Both delta- and gamma-hexonolactones provide templates for the construction of bicyclic lactones in which a new tetrahydropyran ring has been formed from overall elimination of water from the C-2 and C-6 hydroxyl groups. Such studies may provide a strategy for the synthesis of C-glycosides from elimination of water between C-2 and C-6 of heptonolactones.
• Acetonides of α-hydroxy-δ-altronolactones
  作者：Claire J.F. Bichard、Antony J. Fairbanks、George W.J. Fleet、Nigel G. Ramsden、Klaus Vogt、Orla Doherty、Lisa Pearce、David J. Watkin

  DOI：10.1016/s0957-4166(00)82202-8

  日期：1991.1

  The preparation and characterisation of some derivatives of alpha-hydroxy-delta-lactones, in which the delta-carbon substituent on the lactone ring is trans to an adjacent isopropylidene protected diol, are described; the X-ray crystal structures of 3,4-O-isopropylidene-D-altrono-1,5-lactone and of 3,4:6,7-di-O-isopropylidene-D-glycero-D-altro-heptono-1,5-lactone are reported.
• Synthesis of tetrahydropyrans from sugar lactones
  作者：Juan C. Estevez、Antony J. Fairbanks、George W.J. Fleet

  DOI：10.1016/s0040-4020(98)00837-0

  日期：1998.10

  Dehydration of both γ- and δ- hexonolactones, either by intramolecular nucleophilic displacement of triflate leaving groups at C-2, or by Mitsunobu type displacement of the OH-6, provides access to bicyclic lactones which contain tetrahydropyran rings. Reduction or nucleophilic ring opening of these bicyclic lactones furnishes polyfunctionalised tetrahydropyrans in good yield.

  γ-和δ-己内酯的脱水，可以通过在C-2处的三氟甲磺酸酯离去基团的分子内亲核置换，或通过OH-6的Mitsunobu型置换来实现，可以得到含有四氢吡喃环的双环内酯。这些双环内酯的还原或亲核开环以良好的产率提供了多官能化的四氢吡喃。