2-O-tert-butyldimethylsilyl-D-ribono-1,4-lactone | 157453-72-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-tert-butyldimethylsilyl-D-ribono-1,4-lactone
• 英文别名: (3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-one
• CAS: 157453-72-0
• 化学式: C₁₁H₂₂O₅Si
• 分子量: 262.378
• InChiKey: GAGHFSKSXJQFNR-IWSPIJDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-O-tert-butyldimethylsilyl-D-ribono-1,4-lactone 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 17.75h， 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
• 作为产物：
  描述：

  3,4-O-benzylidene-2-O-tert-butyldimethylsilyl-D-ribono-1,5-lactone 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 8.0h， 以97%的产率得到2-O-tert-butyldimethylsilyl-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

• A synthetic route to 3-C-alkyl (or 3-C-phenyl-) 2,3-dideoxy-d-erythro-pentono-1,4-lactones: intermediates in the synthesis of 2(3H)-furanones
  作者：Panolil C. Raveendranath、Vincent J. Blazis、Kwasi Agyei-Aye、Anna K. Hebbler、Lisa N. Gentile、Elma S. Hawkins、Stephen C. Johnson、David C. Baker

  DOI：10.1016/0008-6215(94)80066-9

  日期：1994.2

  A series of 3-C-alkyl- (and 3-C-phenyl-) 2,3-dideoxy-D-erythro-pentono-1,4-lactones, compounds which are important in the synthesis of modified nucleosides and antibiotic sugars, were synthesized from D-ribonolactone. By a route that proceeded via 5-O-protected D-ribonolactone, 5-O-protected 2,3-dideoxy-D-glycero-pent-2-enono-1,4-lactones were synthesized and reacted with R2CuLi or a complex PhSCu(RMgBr)n

  一系列3-C-烷基-（和3-C-苯基-）2，3-二脱氧-D-赤-戊基-1，4-内酯，这些化合物在合成修饰的核苷和抗生素糖中很重要，由D-核糖内酯合成。通过经由5-O-保护的D-核糖内酯进行的途径，合成了5-O-保护的2,3-二脱氧-D-甘油-戊-2-enono-1,4-内酯，并与R2CuLi或络合物反应用PhSCu（RMgBr）n分别得到3-C-烷基或3-C-苯基化合物。提供了O-保护的中间体的制备以及有机金属试剂的选择的细节。