2-allyl-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-β-D-psicofuranose | 145121-59-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-allyl-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-β-D-psicofuranose
• 英文别名: [(3aR,4R,6R,6aR)-2,2-dimethyl-6-(phenylmethoxymethyl)-4-prop-2-enyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]methanol
• CAS: 145121-59-1
• 化学式: C₁₉H₂₆O₅
• 分子量: 334.412
• InChiKey: NEYBUMBFODXCJG-YWTNHNAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  2-allyl-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-β-D-psicofuranose 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以97%的产率得到2-allyl-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-β-D-ribo-hexos-2-ulo-2,5-furanose
  参考文献：
  名称：

  Stereocontrolled synthesis of spirosuccinimide derivative of (+)-hydantocidin

  摘要：

  Synthesis of the spirosuccinimide derivative of (+)-hydantocidin 2 is reported. The key step is a SnCl4-promoted C-glycosidation of the protected D-psicose 3 with allyltrimethlsilane in dichloromethane, which proceeded in good yield and high selectivity; however, C-glycosidation of 3 in acetonitrile afforded the spirooxazoline 6. Synthesis of 2 was achieved in 13% overall yield from 3.

  DOI：

  10.1016/0040-4020(94)01027-w
• 作为产物：
  描述：

  ((3aR,4R,6R,6aR)-4-Allyl-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-trimethyl-silane 在 甲醇 作用下， 生成 2-allyl-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-β-D-psicofuranose
  参考文献：
  名称：

  The Regioselective Opening of 5-O-Benzyl-1,2:3,4-O-isopropylidene-D-psicofuranose With Organostannanes

  摘要：

  DOI：

  10.1016/00404-0399(50)1057o-

文献信息

• The Regioselective Opening of 5-O-Benzyl-1,2:3,4-O-isopropylidene-D-psicofuranose With Organostannanes
  作者：M Dillon

  DOI：10.1016/00404-0399(50)1057o-

  日期：1995.7.31
• Stereocontrolled synthesis of spirosuccinimide derivative of (+)-hydantocidin
  作者：Hiromi Sano、Shigeru Mio、Naoto Tsukaguchi、Soji Sugai

  DOI：10.1016/0040-4020(94)01027-w

  日期：1995.1

  Synthesis of the spirosuccinimide derivative of (+)-hydantocidin 2 is reported. The key step is a SnCl4-promoted C-glycosidation of the protected D-psicose 3 with allyltrimethlsilane in dichloromethane, which proceeded in good yield and high selectivity; however, C-glycosidation of 3 in acetonitrile afforded the spirooxazoline 6. Synthesis of 2 was achieved in 13% overall yield from 3.