5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-D-mannofuranose | 607738-10-3

• 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: 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-D-mannofuranose
• 英文别名: (3aS,5R,6S,6aS)-2,2-dimethyl-5-[(2R)-oxiran-2-yl]-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 607738-10-3
• 化学式: C₁₆H₂₀O₅
• 分子量: 292.332
• InChiKey: DLIZGFMSHQWPGV-MRLBHPIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-D-mannofuranose 在 4 A molecular sieve 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 3,6-di-O-benzyl-1,2-O-isopropylidene-β-D-lyxo-hexofuranos-5-ulose
  参考文献：
  名称：

  Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)

  摘要：

  The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00235-0
• 作为产物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-β-D-mannofuranose 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以89%的产率得到5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-D-mannofuranose
  参考文献：
  名称：

  Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)

  摘要：

  The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00235-0

文献信息

• Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)
  作者：Tadashi Hanaya、Ken-ichi Sugiyama、Heizan Kawamoto、Hiroshi Yamamoto

  DOI：10.1016/s0008-6215(03)00235-0

  日期：2003.7

  The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed. (C) 2003 Elsevier Ltd. All rights reserved.