2,2,2-Trichloro-acetimidic acid (R)-1-[(Z)-3-(tert-butyl-diphenyl-silanyloxy)-propenyl]-pentadecyl ester | 1026173-04-5

• 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: 2,2,2-Trichloro-acetimidic acid (R)-1-[(Z)-3-(tert-butyl-diphenyl-silanyloxy)-propenyl]-pentadecyl ester
• 英文别名: [(Z,4R)-1-[tert-butyl(diphenyl)silyl]oxyoctadec-2-en-4-yl] 2,2,2-trichloroethanimidate
• CAS: 1026173-04-5
• 化学式: C₃₆H₅₄Cl₃NO₂Si
• 分子量: 667.275
• InChiKey: GZVALXQYACSRPA-GFSCNUKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.94
• 重原子数：
  43
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  42.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2,2-Trichloro-acetimidic acid (R)-1-[(Z)-3-(tert-butyl-diphenyl-silanyloxy)-propenyl]-pentadecyl ester 在 potassium dioxotetrahydroxoosmate(VI) 、 甲基磺酰胺 、 AD-mix-β 作用下， 以 水 、 xylene 、 叔丁醇 为溶剂， 反应 11.0h， 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
• 作为产物：
  描述：

  tetradecylmagnesium bromide 在 咪唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 2,2,2-Trichloro-acetimidic acid (R)-1-[(Z)-3-(tert-butyl-diphenyl-silanyloxy)-propenyl]-pentadecyl ester
  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.