tert-Butyl-((3aS,5S,6aS)-2,2-dimethyl-6-methylene-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-diphenyl-silane | 1013635-88-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl-((3aS,5S,6aS)-2,2-dimethyl-6-methylene-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-diphenyl-silane
• CAS: 1013635-88-5
• 化学式: C₂₅H₃₂O₄Si
• 分子量: 424.612
• InChiKey: RYJSJNSMAQHFCR-VJBWXMMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-Butyl-((3aS,5S,6aS)-2,2-dimethyl-6-methylene-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-diphenyl-silane 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 48.0h， 以33%的产率得到3,6-anhydro-5-O-tert-butyldiphenylsilyl-3-C-hydroxymethyl-1,2-O-isopropylidene-β-D-lyxofuranoside
  参考文献：
  名称：

  Oligofuranosides Containing Conformationally Restricted Residues:  Synthesis and Conformational Analysis

  摘要：

  The synthesis of a panel of arabinofuranosyl oligosaccharide analogues (5-13) in which one ring is locked into either the E-3 or E-O conformation is described. The E-3-locked scaffolds 15 and 16 required for the synthesis of 5-10 were prepared in one step from known 1,5-anhydroalditols. A number of routes were explored for the preparation of the E-O-locked monosaccharide derivative 17 needed for the preparation of 11-13. The successful synthesis of 17 was achieved in 17 steps from D-arabinose. Subsequent analysis of 5-13 by H-1 NMR spectroscopy demonstrated that the locked residue does not exert any detectable influence upon the conformers populated by adjacent conformationally unrestricted furanose rings.

  DOI：

  10.1021/jo011127p
• 作为产物：
  描述：

  甲基三苯基溴化膦 、 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-oxo-β-D-arabinofuranose 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 tert-Butyl-((3aS,5S,6aS)-2,2-dimethyl-6-methylene-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-diphenyl-silane
  参考文献：
  名称：

  基于碳水化合物的对映体纯的3-羟基-2-甲基丁酸2-萘基甲基酯的方法

  摘要：

  使用d-葡萄糖，l-木糖以及d-和l-阿拉伯糖的手性库法获得了具有明确定义构型的四种立体异构体3-羟基-2-甲基丁酸。与2-萘基重氮甲烷反应后，分离出作为荧光的2-萘基甲基酯的酸。

  DOI：

  10.1016/j.tetlet.2007.12.104

文献信息

• Carbohydrate chiral-pool approach to four enantiomerically pure 2-naphthylmethyl 3-hydroxy-2-methylbutanoates
  作者：Bogdan Doboszewski、Piet Herdewijn

  DOI：10.1016/j.tet.2008.03.088

  日期：2008.6

  D-Glucose, L-Xylose, and D- and L-arabinose were sources of chirality to obtain four enantiomerically pure 3-hydroxy-2-methylbutanoic acids, which were reacted with 2-naphthyldiazomethane to furnish their fluorescent 2-naphthylmethyl esters. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and antiviral evaluation of α-d-2′,3′-didehydro-2′,3′-dideoxy-3′-C-hydroxymethyl nucleosides
  作者：Kohei Yamada、Hiroyuki Hayakawa、Shinji Sakata、Noriyuki Ashida、Yuichi Yoshimura

  DOI：10.1016/j.bmcl.2010.08.071

  日期：2010.10

  We have identified a selective S(N)2' reaction triggered by iodide ion that leads to the ring-opening of 2,2'-anhydro-alpha-nucleosides. By applying the method, we have synthesized alpha-D-2',3'-didehydro-2',3'-dideoxy- 3'-C-hydroxymethyl nucleosides, designed as potential antiviral agents. (c) 2010 Elsevier Ltd. All rights reserved.