3-O-allyl-2-O-tert-butyldimethylsilyl-5-O-tert-butyldiphenylsilyl-D-ribono-1,4-lactone | 848893-31-2

• 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: 3-O-allyl-2-O-tert-butyldimethylsilyl-5-O-tert-butyldiphenylsilyl-D-ribono-1,4-lactone
• 英文别名: (3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-prop-2-enoxyoxolan-2-one
• CAS: 848893-31-2
• 化学式: C₃₀H₄₄O₅Si₂
• 分子量: 540.847
• InChiKey: RMPHIELCIUSGQN-ZONZVBGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-O-allyl-2-O-tert-butyldimethylsilyl-5-O-tert-butyldiphenylsilyl-D-ribono-1,4-lactone 在 吡啶 、 甲醇 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 Acetic acid (1R,2R,3S)-4-acetoxy-2-allyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-butyl 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
• 作为产物：
  描述：

  3,4-O-benzylidene-2-O-tert-butyldimethylsilyl-D-ribono-1,5-lactone 在 palladium on activated charcoal 、 四(三苯基膦)钯 吡啶 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 26.08h， 生成 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

文献信息

• Synthesis of differentially protected ribitol derivatives from 3,4-O-benzylidene-d-ribono-1,5-lactone
  作者：Dirk J. Lefeber、Peter Steunenberg、Johannes F.G. Vliegenthart、Johannis P. Kamerling

  DOI：10.1016/j.tetasy.2004.12.008

  日期：2005.1

  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.