1-O-trimethylsilyl-2,3,5-tri-O-benzyl-D-ribofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-trimethylsilyl-2,3,5-tri-O-benzyl-D-ribofuranose
• 英文别名: [(3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]oxy-trimethylsilane
• 化学式: C₂₉H₃₆O₅Si
• 分子量: 492.687
• InChiKey: VMHJSBCBBPWGRB-QSVYOFFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-O-trimethylsilyl-2,3,5-tri-O-benzyl-D-ribofuranose 在 碘代三甲硅烷 、 N,N-二异丙基乙胺 、 三苯基氧化膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 isopropyl 2,3,5-tri-O-benzyl-α-D-ribofuranoside
  参考文献：
  名称：

  α-Selective Ribofuranosylation of Alcohols with Ribofuranosyl Iodides and Triphenylphosphine Oxide

  摘要：

  Ribofuranosylation of a variety of alcohols with ribofuranosyl iodides in the presence of a base and triphenylphosphine oxide afforded the corresponding α-ribofuranosides with diastereoselectivities ≥ 99:1. This reaction can be carried out under mildly basic conditions and is thus compatible with acid-sensitive functional groups.

  DOI：

  10.1021/jo500632h

文献信息

• Stereoselective Glycosylation Reaction Starting from 1-O-Trimethylsilyl Sugars by Using Diphenyltin Sulfide and a Catalytic Amount of Active Acidic Species
  作者：Teruaki Mukaiyama、Koki Matsubara

  DOI：10.1246/cl.1992.1041

  日期：1992.6

  1,2-trans-Ribofuranosides are stereoselectively synthesized from 1-O-trimethylsilyl ribofuranose and trimethylsilyl ethers in the presence of a catalytic amount of Me3SiOTf using Ph2Sn=S as an additive, while 1,2-cis-ribofuranosides and 1,2-cis-glucopyranosides are prepared predominantly in the coexistence of LiClO4 in the above reaction.

  在催化量的 Me3SiOTf 存在下，使用 Ph2Sn=S 作为添加剂，从 1-O-三甲基甲硅烷基呋喃核糖和三甲基甲硅烷基醚立体选择性地合成 1,2-反式-呋喃核糖苷，而 1,2-顺式-呋喃核糖苷和 1,2-在上述反应中，顺式吡喃葡萄糖苷主要在 LiClO4 共存下制备。
• α-Selective Ribofuranosylation of Alcohols with Ribofuranosyl Iodides and Triphenylphosphine Oxide
  作者：Natsuhisa Oka、Rin Kajino、Kaoru Takeuchi、Haruna Nagakawa、Kaori Ando

  DOI：10.1021/jo500632h

  日期：2014.8.15

  Ribofuranosylation of a variety of alcohols with ribofuranosyl iodides in the presence of a base and triphenylphosphine oxide afforded the corresponding α-ribofuranosides with diastereoselectivities ≥ 99:1. This reaction can be carried out under mildly basic conditions and is thus compatible with acid-sensitive functional groups.