5-deoxy-6-O-t-butyldimethylsilyl-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hexofuranose | 178686-43-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-deoxy-6-O-t-butyldimethylsilyl-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hexofuranose
• CAS: 178686-43-6
• 化学式: C₁₆H₃₂O₅Si
• 分子量: 332.513
• InChiKey: NVAIQKLGYPPCRT-OQMKEHIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-deoxy-6-O-t-butyldimethylsilyl-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hexofuranose 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 14.5h， 生成 2-((3aR,5R,6R,6aR)-6-Allyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethanol
  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 、 溶剂黄146 、 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 18.0h， 生成 5-deoxy-6-O-t-butyldimethylsilyl-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.