2,2-Dimethyl-propionic acid (2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6,6-bis-ethylsulfanyl-2-methanesulfonyloxy-hexyl ester | 946134-24-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-Dimethyl-propionic acid (2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6,6-bis-ethylsulfanyl-2-methanesulfonyloxy-hexyl ester
• 英文别名: [(2R,3R,4S,5R)-6,6-bis(ethylsulfanyl)-2-methylsulfonyloxy-3,4,5-tris(phenylmethoxy)hexyl] 2,2-dimethylpropanoate
• CAS: 946134-24-3
• 化学式: C₃₇H₅₀O₈S₃
• 分子量: 718.997
• InChiKey: VTKIGYKDLHYRIB-ALMGMPQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  48
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  156
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6,6-bis-ethylsulfanyl-2-methanesulfonyloxy-hexyl ester 在 氢氧化钾 、 碘 、 calcium carbonate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 水 为溶剂， 反应 31.25h， 生成 1-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-2-trimethylsilylacetylene
  参考文献：
  名称：

  Selective Synthesis of α-C-(Alkynyl)-galactosides by an Efficient Tandem Reaction

  摘要：

  Several alpha-C-(alkynyl)-galacto sides were synthesized using a tandem reaction involving the addition of a metal alkynylide to a chiral acyclic epoxyaldehyde, followed by an in situ closure of the generated alkoxide on the epoxide function.

  DOI：

  10.1021/jo0519817
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-galactose diethyldithioacetal 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 2,2-Dimethyl-propionic acid (2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6,6-bis-ethylsulfanyl-2-methanesulfonyloxy-hexyl ester
  参考文献：
  名称：

  Selective Synthesis of α-C-(Alkynyl)-galactosides by an Efficient Tandem Reaction

  摘要：

  Several alpha-C-(alkynyl)-galacto sides were synthesized using a tandem reaction involving the addition of a metal alkynylide to a chiral acyclic epoxyaldehyde, followed by an in situ closure of the generated alkoxide on the epoxide function.

  DOI：

  10.1021/jo0519817

文献信息

• Traces of Water as a Key Parameter for the Formation of an Epoxydithio Compound
  作者：Arnaud Haudrechy、Aline Banchet、Stéphane Guillarme

  DOI：10.1055/s-2007-980348

  日期：2007.6

  The presence of a small amount of water has proven to be necessary in order to obtain a reproducible amount of an epoxydithio compound. Conversely, under anhydrous conditions, an interesting thiosugar derivative results from a selective internal attack of sulfur, followed by an ‘ethyl’ transfer.

  实践证明，为了获得可重复的环氧二硫化合物，必须存在少量的水。相反，在无水条件下，硫的选择性内部攻击会产生一种有趣的硫代糖衍生物，随后发生“乙基”转移。
• Selective Synthesis of α-<i>C</i>-(Alkynyl)-galactosides by an Efficient Tandem Reaction
  作者：Stéphane Guillarme、Karen Plé、Arnaud Haudrechy

  DOI：10.1021/jo0519817

  日期：2006.2.1

  Several alpha-C-(alkynyl)-galacto sides were synthesized using a tandem reaction involving the addition of a metal alkynylide to a chiral acyclic epoxyaldehyde, followed by an in situ closure of the generated alkoxide on the epoxide function.