2,3-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone | 134472-76-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone
• 英文别名: (3aS,6S,6aS)-2,2-dimethyl-6-[(1R,2R)-1,2,3-trihydroxypropyl]-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 134472-76-7
• 化学式: C₁₀H₁₆O₇
• 分子量: 248.233
• InChiKey: NHEGYTHCQWFLNI-HEIBUPTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone 在 咪唑 、 camphor-10-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 2.33h， 生成 7-O-tert-butyldiphenylsilyl-2,3:5,6-di-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone
  参考文献：
  名称：

  Acetonides of heptonolactones: Powerful chirons

  摘要：

  Heptonolactones, in which all the functional groups except one can be protected with a single ketal protecting group, have great potential as starting materials within the chiral pool. The practical synthesis and characterisation of acetonides of glycero-talo- and glycero-galacto-heptono-lactone are described. X-ray crystal structures of D-glycero-D-talo-heptono-1,4-lactone and 2,3:5,6-di-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone are reported.

  DOI：

  10.1016/s0957-4166(00)82201-6
• 作为产物：
  描述：

  D-mannose 在 硫酸 、 camphor-10-sulfonic acid 、 溶剂黄146 、 三氟乙酸 作用下， 以 水 、 丙酮 为溶剂， 反应 59.0h， 生成 2,3-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone
  参考文献：
  名称：

  Acetonides of heptonolactones: Powerful chirons

  摘要：

  Heptonolactones, in which all the functional groups except one can be protected with a single ketal protecting group, have great potential as starting materials within the chiral pool. The practical synthesis and characterisation of acetonides of glycero-talo- and glycero-galacto-heptono-lactone are described. X-ray crystal structures of D-glycero-D-talo-heptono-1,4-lactone and 2,3:5,6-di-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone are reported.

  DOI：

  10.1016/s0957-4166(00)82201-6

文献信息

• Acetonides of heptonolactones: Powerful chirons
  作者：Annabel R. Beacham、Ian Bruce、Samuel Choi、Orla Doherty、Antony J. Fairbanks、George W.J. Fleet、Ben M. Skead、Josephine M. Peach、John Saunders、David J. Walking

  DOI：10.1016/s0957-4166(00)82201-6

  日期：1991.1

  Heptonolactones, in which all the functional groups except one can be protected with a single ketal protecting group, have great potential as starting materials within the chiral pool. The practical synthesis and characterisation of acetonides of glycero-talo- and glycero-galacto-heptono-lactone are described. X-ray crystal structures of D-glycero-D-talo-heptono-1,4-lactone and 2,3:5,6-di-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone are reported.