Methyl 2,3:4,5:6,7:8,9:10,11-Penta-O-isopropylidene-D-glycero-D-talo-L-talo-undeconate | 132047-03-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2,3:4,5:6,7:8,9:10,11-Penta-O-isopropylidene-D-glycero-D-talo-L-talo-undeconate
• 英文别名: methyl (4R,5R)-5-[(4R,5S)-5-[(4S,5S)-5-[(4S,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• CAS: 132047-03-1
• 化学式: C₂₇H₄₄O₁₂
• 分子量: 560.639
• InChiKey: GHROCCLOKNMEKQ-BCUPLPLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Methyl 2,3:4,5:6,7:8,9:10,11-Penta-O-isopropylidene-D-glycero-D-talo-L-talo-undeconate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到2,3:4,5:6,7:8,9:10,11-Penta-O-isopropylidene-D-glycero-D-talo-L-talo-undecose
  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：

  5-O-(Trimethylsilyl)-6,7:8,9:10,11-tri-O-isopropylidene-D-glycero-D-talo-L-talo-undecono-1,4-lactone 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以57%的产率得到Methyl 2,3:4,5:6,7:8,9:10,11-Penta-O-isopropylidene-D-glycero-D-talo-L-talo-undeconate
  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

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：——