3-O-allyl-6-O-t-butyldimethylsilyl-5-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hexofuranose | 159677-42-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-allyl-6-O-t-butyldimethylsilyl-5-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hexofuranose
• 英文别名: 2-[(3aR,5R,6R,6aR)-2,2,6-trimethyl-6-prop-2-enoxy-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]ethoxy-tert-butyl-dimethylsilane
• CAS: 159677-42-6
• 化学式: C₁₉H₃₆O₅Si
• 分子量: 372.577
• InChiKey: XTIQKKDFVXLPQY-YYAJDYIMSA-N

物化性质

• 沸点：
  381.331±42.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.012±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-O-allyl-6-O-t-butyldimethylsilyl-5-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hexofuranose 在 重铬酸吡啶 、 4 A molecular sieve 、 盐酸羟胺 、 四丁基氟化铵 、 sodium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Synthetic studies on zoapatanol: Construction of oxepanes via an intramolecular 1,3-dipolar cycloaddition strategy

  摘要：

  The nitrones derived from beta-allyloxyaldehydes with a beta-quaternary centre cyclized to give six- instead of seven-membered O-heterocycles exclusively whereas a nitrile oxide derived from a gamma-allyloxyaldehyde with a gamma-quaternary centre cyclized to yield an oxepane ring as the sole product. Using the latter intramolecular nitrile oxide cycloaddition as the key step, optically active oxepane 5, which is a suitable intermediate for a synthesis of zoapatanol 1, has been constructed from D-glucose. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00149-8
• 作为产物：
  描述：

  1,2,5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose 在 咪唑 、 4-二甲氨基吡啶 、 sodium hydroxide 、 dimethyl sulfide borane 、 双氧水 、 碘 、 sodium hydride 、 溶剂黄146 、 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 30.5h， 生成 3-O-allyl-6-O-t-butyldimethylsilyl-5-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hexofuranose
  参考文献：
  名称：

  Synthetic studies on zoapatanol: Construction of oxepanes via an intramolecular 1,3-dipolar cycloaddition strategy

  摘要：

  The nitrones derived from beta-allyloxyaldehydes with a beta-quaternary centre cyclized to give six- instead of seven-membered O-heterocycles exclusively whereas a nitrile oxide derived from a gamma-allyloxyaldehyde with a gamma-quaternary centre cyclized to yield an oxepane ring as the sole product. Using the latter intramolecular nitrile oxide cycloaddition as the key step, optically active oxepane 5, which is a suitable intermediate for a synthesis of zoapatanol 1, has been constructed from D-glucose. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00149-8

文献信息

• An enantiospecific approach to an oxepane related to zoapatanol via a 1,3-dipolar cycloaddition
  作者：Tony K.M. Shing、Ching-Hung Wong

  DOI：10.1016/0957-4166(94)80143-6

  日期：1994.7

  The optically active oxepane 2, which is a suitable intermediate for a synthesis of zoapatanol 1, has been constructed from D-glucose invoking an intramolecular nitrile oxide cycloaddtion as the key step.
• Synthetic studies on zoapatanol: Construction of oxepanes via an intramolecular 1,3-dipolar cycloaddition strategy
  作者：Tony K.M. Shing、Ching-Hung Wong、Ting Yip

  DOI：10.1016/0957-4166(96)00149-8

  日期：1996.5

  The nitrones derived from beta-allyloxyaldehydes with a beta-quaternary centre cyclized to give six- instead of seven-membered O-heterocycles exclusively whereas a nitrile oxide derived from a gamma-allyloxyaldehyde with a gamma-quaternary centre cyclized to yield an oxepane ring as the sole product. Using the latter intramolecular nitrile oxide cycloaddition as the key step, optically active oxepane 5, which is a suitable intermediate for a synthesis of zoapatanol 1, has been constructed from D-glucose. Copyright (C) 1996 Elsevier Science Ltd