3,4:6,7-di-O-isopropylidene-D-glycero-D-galacto-heptono-1,5-lactone | 116730-60-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3,4:6,7-di-O-isopropylidene-D-glycero-D-galacto-heptono-1,5-lactone
• 英文别名: (3aR,4R,7R,7aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one
• CAS: 116730-60-0
• 化学式: C₁₃H₂₀O₇
• 分子量: 288.298
• InChiKey: HQVJTKTXELKPID-IGORNWKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4:6,7-di-O-isopropylidene-D-glycero-D-galacto-heptono-1,5-lactone 在 吡啶 、 sodium acetate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.03h， 生成 3,4:6,7-di-O-isopropylidene-2-O-trifluoromethanesulphonyl-D-glycero-D-talo-heptono-1,5-lactone
  参考文献：
  名称：

  Retention and apparent inversion during azide displacement of α-triflates of 15-lactones

  摘要：

  DOI：

  10.1016/s0040-4020(01)97581-7
• 作为产物：
  描述：

  D-mannose 在 硫酸 作用下， 以 水 为溶剂， 反应 9.0h， 生成 3,4:6,7-di-O-isopropylidene-D-glycero-D-galacto-heptono-1,5-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

• A practical synthesis of 2-deoxy aldonolactones via a SmI2-mediated α-deoxygenation reaction
  作者：Stephen Hanessian、Christian Girard、Jose Luis Chiara

  DOI：10.1016/s0040-4039(00)92313-x

  日期：1992.1

  A one-step deoxygenation of 2-hydroxylactones or their acetates is possible using samarium diiodide as an electron-transfer reagent in conjunction with a proton source.
• Inhibition of α-mannosidases by seven carbon sugars: Synthesis of some seven carbon analogues of mannofuranose
  作者：Paul M. Myerscough、Antony J. Fairbanks、Aled H. Jones、Ian Bruce、Sik-man S. Choi、George W.J. Fleet、Samer S. Al-Daher、Isabelle Cenci di Bello、Bryan Winchester

  DOI：10.1016/s0040-4020(01)89046-3

  日期：——

  The effects on human liver glycosidases of some seven carbon analogues of mannopyranose and mannofuranose are compared with those of deoxymannojirimycin and DIM. The syntheses of the seven carbon mannofuranose analogues, alpha-(aminomethyl)-1-deoxy-mannofuranose and of alpha-homoDIM, are described.
• 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.
• Retention and apparent inversion during azide displacement of α-triflates of 15-lactones
  作者：Ian Bruce、George W.J. Fleet、Aarti Girdhar、Martin Haraldsson、Josephine M. Peach、David J. Watkin

  DOI：10.1016/s0040-4020(01)97581-7

  日期：1990.1