1,2-Dideoxy-4,5,6-tri-O-benzyl-8-O-tert-butyldimethylsilyl-D-gluco-oct-1-eno-3-ulopyranose

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-Dideoxy-4,5,6-tri-O-benzyl-8-O-tert-butyldimethylsilyl-D-gluco-oct-1-eno-3-ulopyranose
• 英文别名: (3R,4S,5R,6R)-6-tert-(butyldimethylsilyloxymethyl)-3,4,5-tris(benzyloxy)-2-vinyl-tetrahydro-4H-pyran-2-ol；(3R,4S,5R,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-ethenyl-3,4,5-tris(phenylmethoxy)oxan-2-ol
• 化学式: C₃₅H₄₆O₆Si
• 分子量: 590.832
• InChiKey: PZIIGWDUFNWDPC-NCSHYKNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.04
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-Dideoxy-4,5,6-tri-O-benzyl-8-O-tert-butyldimethylsilyl-D-gluco-oct-1-eno-3-ulopyranose 在 calcium sulfate 、 三氟甲磺酸 作用下， 以 乙腈 为溶剂， 以89%的产率得到(1R,2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-vinyl-6,8-dioxabicyclo[3.2.1]octane
  参考文献：
  名称：

  Syntheses of a partially benzylated derivative of the anhydro-d-altro-heptulose found in Coriaria japonica A and of its analogs

  摘要：

  A partially benzylated derivative of anhydro-D-altro-heptulose found in Coriaria japonica A, which is a synthetically useful unit, was successfully synthesized from a D-mannose derivative by a novel synthetic approach involving the intramolecular O-ketopyranosylation reaction developed by us. This synthetic approach was also applicable to the preparation of its four analogs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.068
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-6-O-[tert-butyl(dimethyl)silyl]-D-glucono-1,5-lactone 、 乙烯基氯化镁 以 四氢呋喃 为溶剂， 反应 3.0h， 以80%的产率得到1,2-Dideoxy-4,5,6-tri-O-benzyl-8-O-tert-butyldimethylsilyl-D-gluco-oct-1-eno-3-ulopyranose
  参考文献：
  名称：

  Syntheses of a partially benzylated derivative of the anhydro-d-altro-heptulose found in Coriaria japonica A and of its analogs

  摘要：

  A partially benzylated derivative of anhydro-D-altro-heptulose found in Coriaria japonica A, which is a synthetically useful unit, was successfully synthesized from a D-mannose derivative by a novel synthetic approach involving the intramolecular O-ketopyranosylation reaction developed by us. This synthetic approach was also applicable to the preparation of its four analogs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.068

文献信息

• Montmorillonite K-10 Clay Assisted Transformation of Vinylketoses into Spirochromans and Arylketoses
  作者：Peter A. V. van Hooft、Paul F. van Swieten、Gijsbert A. van der Marel、Constant A. A. van Boeckel、Jacques H. van Boom

  DOI：10.1055/s-2001-10761

  日期：——

  Montmorillonite K-10 clay mediated synthesis of spirochromans and arylketoses starting from 1,2-dideoxy-4,5,6-tri-O-benzyl-8-O-tert-butyldimethylsilyl-d-gluco-oct-1-eno-3-ulopyranose (6) is presented. In addition, valuable chiral synthons were obtained by conversion of the spirochromans and arylketoses into the open chain derivatives via Vasella rearrangement.

  蒙脱石K-10黏土介导的螺旋色满和芳基酮糖合成，起始于1,2-二脱氧-4,5,6-三-O-苄基-8-O-叔丁基二甲基硅基-d-葡萄辛-1-烯-3-呋喃糖（6）的研究。此外，通过Vasella重排将螺旋色满和芳基酮糖转化为开链衍生物，获得了有价值的 chiral synthons。