Carbonic acid allyl ester (2R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-tetrahydro-furan-3-yl ester | 848893-30-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: Carbonic acid allyl ester (2R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-oxooxolan-3-yl] prop-2-enyl carbonate
• CAS: 848893-30-1
• 化学式: C₃₁H₄₄O₇Si₂
• 分子量: 584.857
• InChiKey: POLJGKLWCKWCCB-ZONZVBGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Carbonic acid allyl ester (2R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-tetrahydro-furan-3-yl ester 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以75%的产率得到3-O-allyl-2-O-tert-butyldimethylsilyl-5-O-tert-butyldiphenylsilyl-D-ribono-1,4-lactone
  参考文献：
  名称：

  Synthesis of differentially protected ribitol derivatives from 3,4-O-benzylidene-d-ribono-1,5-lactone

  摘要：

  Several differentially protected ribitol derivatives were synthesised using 3,4-O-benzylidene-D-ribono-1,5-lactone as versatile starting compounds for oligosaccharide synthesis. The obtained ribitol derivatives allow the regiospecific coupling of glycosyl donors to either of the hydroxyl groups of ribitol and can be applied for the preparation of polyhydroxylated compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.12.008
• 作为产物：
  描述：

  3,4-O-benzylidene-2-O-tert-butyldimethylsilyl-D-ribono-1,5-lactone 在 palladium on activated charcoal 吡啶 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 25.75h， 生成 Carbonic acid allyl ester (2R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis of differentially protected ribitol derivatives from 3,4-O-benzylidene-d-ribono-1,5-lactone

  摘要：

  Several differentially protected ribitol derivatives were synthesised using 3,4-O-benzylidene-D-ribono-1,5-lactone as versatile starting compounds for oligosaccharide synthesis. The obtained ribitol derivatives allow the regiospecific coupling of glycosyl donors to either of the hydroxyl groups of ribitol and can be applied for the preparation of polyhydroxylated compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.12.008