2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranosyl isothiocyanate | 1268627-59-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranosyl isothiocyanate
• 英文别名: [(2S,3S,4R,5R)-2-[(1R)-1,2-bis[[tert-butyl(dimethyl)silyl]oxy]ethyl]-4-[tert-butyl(dimethyl)silyl]oxy-5-isothiocyanatooxolan-3-yl]oxy-tert-butyl-dimethylsilane
• CAS: 1268627-59-3
• 化学式: C₃₁H₆₇NO₅SSi₄
• 分子量: 678.285
• InChiKey: XJYLMVUWSNJGPM-LXSUACKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.01
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  per-O-TBS-D-Galf 、 potassium thioacyanate 在 碘代三甲硅烷 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 48.5h， 以54%的产率得到2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranosyl isothiocyanate
  参考文献：
  名称：

  Synthesis and conformational analysis of 1,2-cis fused bicyclic α-d-galactofuranosyl thiocarbamate from per-O-tert-butyldimethylsilyl-β-d-galactofuranosyl isothiocyanate

  摘要：

  Per-O-tert-butyldimethylsilyl-alpha,beta-D-galactofuranosyl isothiocyanate (4) was synthesized by the reaction of per-O-TBS-beta-D-galactofuranose (1) with KSCN, promoted by TMSI. Upon O-desilylation (1,2-dideoxy-alpha-D-galactofuranoso)[1,2d]-1,3-oxazolidine-2-thione (6), the cis-fused bicyclic thiocarbamate was obtained as the only product. Conformational analysis, aided by molecular modelling, showed two stable twist forms (T-3(4) and T-4(o)) for the five-membered sugar ring in 6. In aqueous solution, the equilibrium favours the first conformation (3:1 ratio). On the other hand, this ratio decreases for less polar solvents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.11.013