(2R,3R,4R)-1-t-butyldiphenylsilyloxy-2-trichloroacetylamino-3,4-octadecanediol | 287381-79-7

• 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: (2R,3R,4R)-1-t-butyldiphenylsilyloxy-2-trichloroacetylamino-3,4-octadecanediol
• 英文别名: N-[(2R,3R,4R)-1-[tert-butyl(diphenyl)silyl]oxy-3,4-dihydroxyoctadecan-2-yl]-2,2,2-trichloroacetamide
• CAS: 287381-79-7
• 化学式: C₃₆H₅₆Cl₃NO₄Si
• 分子量: 701.289
• InChiKey: ZWXQROIBFFWXEL-WRVRXEDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.23
• 重原子数：
  45
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-1-t-butyldiphenylsilyloxy-2-trichloroacetylamino-3,4-octadecanediol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 2,2,2-Trichloro-N-((1R,2R,3R)-2,3-dihydroxy-1-hydroxymethyl-heptadecyl)-acetamide
  参考文献：
  名称：

  Enantioselective synthesis of lyxo -(2 R ,3 R ,4 R )-C 18 -phytosphingosine using double stereodifferentiation 1

  摘要：

  lyxo-C-18-Phytosphingosine can be synthesized by the cis-dihydroxylation of an (E)-allylic trichloroacetamide obtained by an Overman rearrangement. A double stereodifferentiation using AD-mix-beta and an enantiomerically enriched (S)-allylic trichloroacetamide allowed the first synthesis of lyxo-(2R,3R,4R)-C-18-phytosphingosine with high diastereoselectivity (de = 94%) and excellent enantioselectivity (ee = 93%). This sphingosine was fully characterized by the physical and spectral data of the corresponding tetraacetate. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00106-3
• 作为产物：
  描述：

  (4R,2Z)-1-(t-butyldiphenylsilyloxy)-2-octadecen-4-ol 在 potassium dioxotetrahydroxoosmate(VI) 、 甲基磺酰胺 、 AD-mix-β 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 xylene 、 叔丁醇 为溶剂， 反应 12.0h， 生成 (2R,3R,4R)-1-t-butyldiphenylsilyloxy-2-trichloroacetylamino-3,4-octadecanediol
  参考文献：
  名称：

  Enantioselective synthesis of lyxo -(2 R ,3 R ,4 R )-C 18 -phytosphingosine using double stereodifferentiation 1

  摘要：

  lyxo-C-18-Phytosphingosine can be synthesized by the cis-dihydroxylation of an (E)-allylic trichloroacetamide obtained by an Overman rearrangement. A double stereodifferentiation using AD-mix-beta and an enantiomerically enriched (S)-allylic trichloroacetamide allowed the first synthesis of lyxo-(2R,3R,4R)-C-18-phytosphingosine with high diastereoselectivity (de = 94%) and excellent enantioselectivity (ee = 93%). This sphingosine was fully characterized by the physical and spectral data of the corresponding tetraacetate. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00106-3

文献信息

• Enantioselective synthesis of lyxo -(2 R ,3 R ,4 R )-C 18 -phytosphingosine using double stereodifferentiation 1
  作者：Catherine Martin、William Prünck、Michel Bortolussi、Robert Bloch

  DOI：10.1016/s0957-4166(00)00106-3

  日期：2000.4

  lyxo-C-18-Phytosphingosine can be synthesized by the cis-dihydroxylation of an (E)-allylic trichloroacetamide obtained by an Overman rearrangement. A double stereodifferentiation using AD-mix-beta and an enantiomerically enriched (S)-allylic trichloroacetamide allowed the first synthesis of lyxo-(2R,3R,4R)-C-18-phytosphingosine with high diastereoselectivity (de = 94%) and excellent enantioselectivity (ee = 93%). This sphingosine was fully characterized by the physical and spectral data of the corresponding tetraacetate. (C) 2000 Elsevier Science Ltd. All rights reserved.