2,3:6,7-Di-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone | 132047-06-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3:6,7-Di-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone
• 英文别名: (3aS,6S,6aS)-6-[(R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 132047-06-4
• 化学式: C₁₃H₂₀O₇
• 分子量: 288.298
• InChiKey: ZAVQWRAEZCFXGE-ZJDVBMNYSA-N

物化性质

• 沸点：
  425.0±45.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  2
• 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：

  2,3:6,7-Di-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone 在 吡啶 、 甲醇 、 二环己烷并-18-冠醚-6 、 potassium permanganate 、 sodium-potassium tartrate 、 三氟化硼乙醚 、 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 5-O-(Trimethylsilyl)-6,7:8,9:10,11-tri-O-isopropylidene-D-glycero-D-talo-L-talo-undecono-1,4-lactone
  参考文献：
  名称：

  Ascent of the aldose series by four carbon atoms: total synthesis of D-glycero-D-talo-L-talo-undecose pentaacetonide

  摘要：

  Enantiomerically pure undecose acetonide 9 was synthesized, through heptose intermediate 5, starting with D-glyceraldehyde acetonide (1). The key steps were two consecutive four-carbon homologations, each consisting of four reactions: (i) stereoselective elongation of the aldehyde precursor with 2-(trimethylsiloxy)furan, giving C(n+4) butenolide templates 2 and 6, (ii) anti-selective cis-dihydroxylation of the butenolide double bond, giving fully functionalized lactones 3 and 7, (iii) lactone ring opening and protection, giving open-chain methyl esters 4 and 8, and (iv) DIBAL reduction to aldoses 5 and 9. At the end of the eight-step sequence, undecose 9 was prepared in a 5.1% overall yield, which corresponded to a 69.5% average yield per step.

  DOI：

  10.1021/jo00006a032
• 作为产物：
  描述：

  D-mannose 在 硫酸 、 camphor-10-sulfonic acid 、 三氟乙酸 作用下， 以 水 、 丙酮 为溶剂， 反应 41.0h， 生成 2,3:6,7-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

文献信息

• CASIRAGHI, GIOVANNI;COLOMBO, LINO;RASSU, GLORIA;SPANU, PIETRO, J. ORG. CHEM., 56,(1991) N, C. 2135-2139
  作者：CASIRAGHI, GIOVANNI、COLOMBO, LINO、RASSU, GLORIA、SPANU, PIETRO

  DOI：——

  日期：——
• Ascent of the aldose series by four carbon atoms: total synthesis of D-glycero-D-talo-L-talo-undecose pentaacetonide
  作者：Giovanni Casiraghi、Lino Colombo、Gloria Rassu、Pietro Spanu

  DOI：10.1021/jo00006a032

  日期：1991.3

  Enantiomerically pure undecose acetonide 9 was synthesized, through heptose intermediate 5, starting with D-glyceraldehyde acetonide (1). The key steps were two consecutive four-carbon homologations, each consisting of four reactions: (i) stereoselective elongation of the aldehyde precursor with 2-(trimethylsiloxy)furan, giving C(n+4) butenolide templates 2 and 6, (ii) anti-selective cis-dihydroxylation of the butenolide double bond, giving fully functionalized lactones 3 and 7, (iii) lactone ring opening and protection, giving open-chain methyl esters 4 and 8, and (iv) DIBAL reduction to aldoses 5 and 9. At the end of the eight-step sequence, undecose 9 was prepared in a 5.1% overall yield, which corresponded to a 69.5% average yield per step.
• 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.