1,2-O-diacetyl-3,4-O-isopropylidene-D-threitol | 125284-42-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2-O-diacetyl-3,4-O-isopropylidene-D-threitol
• 英文别名: [(2R)-2-acetyloxy-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl] acetate
• CAS: 125284-42-6
• 化学式: C₁₁H₁₈O₆
• 分子量: 246.26
• InChiKey: MHLXBUGVHWKNBD-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1,2-O-diacetyl-3,4-O-isopropylidene-D-threitol 在 4-二甲氨基吡啶 、 溶剂黄146 作用下， 生成 (D)-threitol tetraacetate
  参考文献：
  名称：

  Enantiomerically pure 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives (naked sugars) as synthetic intermediates. XII. Highly stereoselective total syntheses of octoses and derivatives

  摘要：

  Mukaiyama cross aldolizations of (R)-2,3-O-isopropylideneglyceraldehyde (10) with (1R,4S,5R,6R)-5-exo, 6-exo-(isopropylidenedioxy)-7-oxabicyclo[2.2.1]heptan-2-one ((+)-8) were highly diastereoselective and led to the corresponding u,u,l or SYNCAT ((+)-11) and u,u,u or ANCAT ((-)-21) aldols, respectively. The results were interpreted in terms of extended open transition state models with (ul,lk) and (ul,ul) topicities, respectively, which minimize steric repulsions. Aldols (+)-11 and (-)-21 were converted into (tert-butyl)dimethylsilyl 6-O-acetyl-2,3:7, 8-di-O-isopropylidene-D-glycero-L-talo-alpha-octofuranosid-5-ulose ((-)-18) and its D-talo diastereomer ((+)-28), respectively. Reduction of (-)-18 with LiEt3BH in THF gave, after deprotection, the known D-threo-L-talo-octose ((-)-4). Reduction of (-)-18 with (i-Bu)2AlH/THF gave, after deprotection, the unknown D-threo-D-allo-octose ((+)-5) with high stereoselectivity. Similarly, the unknown D-erythro-D-talo-octose ((+)-6) and D-erythro-L-allo-octose ((-)-7) were derived from (+)-28 through reduction with LiB(s-Bu)3H and (i-Bu)2AlH, respectively.

  DOI：

  10.1021/jo00003a041
• 作为产物：
  描述：

  [(3aR,4S,6R,6aS)-4-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl] (2S)-2-acetyloxy-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]acetate 、 锂硼氢 以68%的产率得到
  参考文献：
  名称：

  JEGANATHAN, SURULIAPPA;VOGEL, PIERRE, J. CHEM. SOC. CHEM. COMMUN.,(1989) N5, C. 993-995

  摘要：

  DOI：

文献信息

• Synthesis of higher-carbon sugars via cross-aldolization of 7-oxanorbornan-2-one and carbohydrate aldehyde derivatives
  作者：Suruliappa Jeganathan、Pierre Vogel

  DOI：10.1039/c39890000993

  日期：——

  The TiCl4-induced condensation of (+)-(1S,4S,5S,6S)-5,6-isopropylidenedioxy-2-t-butyldimethylsilyloxy-7-oxabicyclo[2.2.1]hept-2-ene with 2,3-O-isopropylidene-D-glyceraldehyde was highly stereoselective, giving a product that was converted with high stereoselectivity into protected D-erythro-D-talo-octose and D-erthro-L-allo-octose.

  TiCl 4诱导的（+）-（1 S，4 S，5 S，6 S）-5,6-异丙基二烯二氧基-2-叔丁基二甲基甲硅烷氧基-7-氧杂双环[2.2.1]庚-2-烯的缩合与2,3- ö异亚丙基d甘油醛是高度立体选择性，从而，将其转变高立体选择性成保护的产品d -赤- d -距骨-octose和d - erthro -大号-异体-octose。
• JEGANATHAN, SURULIAPPA;VOGEL, PIERRE, J. ORG. CHEM., 56,(1991) N, C. 1139-1142
  作者：JEGANATHAN, SURULIAPPA、VOGEL, PIERRE

  DOI：——

  日期：——