isopropyl 2,3,5-tri-O-acetyl-β-D-ribofuranoside | 1198762-41-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 2,3,5-tri-O-acetyl-β-D-ribofuranoside
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-propan-2-yloxyoxolan-2-yl]methyl acetate
• CAS: 1198762-41-2
• 化学式: C₁₄H₂₂O₈
• 分子量: 318.324
• InChiKey: DFNZAORHSSXEMA-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  isopropyl 2,3,5-tri-O-acetyl-β-D-ribofuranoside 在 Candida antarctica B lipase 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以24%的产率得到isopropyl 2,3-di-O-acetyl-β -D-ribofuranoside
  参考文献：
  名称：

  Candida antarcticaB lipase-catalysed alcoholysis of peracetylated alkyl D-ribofuranosides

  摘要：

  Candida antarctica B lipase (CAL-B) catalysed alcoholysis of a series of peracetylated alkyl alpha, beta-D-ribofuranosides was assayed. Methyl and ethyl 2,3-di-O-acetyl-alpha, beta-D-ribofuranosides enriched in the alpha-anomer were regioselectively prepared through this enzymatic deacetylation in 33% and 43% yield, respectively, the latter being a new compound. Isopropyl 2,3,5-tri-O-acetyl-beta-D-ribofuranoside gave the new isopropyl 2,3-di-O-acetyl-beta-D-ribofuranoside in 24% yield. The anomeric substituent affects the regioselectivity of the reaction, since n-propyl and n-butyl alpha, beta-D-ribofuranosides reacted without selectivity.

  DOI：

  10.3109/10242422.2010.501105
• 作为产物：
  描述：

  异丙醇 、 四乙酰核糖 在 碘 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以80%的产率得到isopropyl 2,3,5-tri-O-acetyl-β-D-ribofuranoside
  参考文献：
  名称：

  Iodine-promoted ribosylation leads to a facile acetonide-forming reaction

  摘要：

  Iodine not only promotes smooth beta-selective glycosylation of ribose tetra-acetate under exceptionally mild conditions, it also catalyzes an expedient acetonide-forming reaction in this system when dry acetone is used as a solvent. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.08.026