tert-butyl (1S,2R)-1-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-hydroxy-2-phenylethylcarbamate | 350503-44-5

• 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: tert-butyl (1S,2R)-1-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-hydroxy-2-phenylethylcarbamate
• 英文别名: tert-butyl N-[(1R,2S)-3-[tert-butyl(diphenyl)silyl]oxy-1-hydroxy-1-phenylpropan-2-yl]carbamate
• CAS: 350503-44-5
• 化学式: C₃₀H₃₉NO₄Si
• 分子量: 505.729
• InChiKey: MTZULFARRVIPAT-RRPNLBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,2R)-1-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-hydroxy-2-phenylethylcarbamate 在 盐酸 、 4-二甲氨基吡啶 、 正丁基锂 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 甲苯 、 苯 为溶剂， 反应 19.75h， 生成 diethyl (3S,4R)-1,1-difluoro-4-hydroxy-3-(palmitoylamino)-4-phenylbutylphosphonate
  参考文献：
  名称：

  Synthesis of non-competitive inhibitors of Sphingomyelinases with significant activity

  摘要：

  A series of short-chain analogues of N-palmitoylsphingosine-1-phosphate, modified by replacement of the phosphate and the long alkenyl side chain with hydrolytically stable difluoromethylene phosphonate and phenyl, respectively, were prepared to study the structure-activity relationship for inhibition of sphingomyelinase. The study revealed that inhibition is highly dependent upon the stereochemistry of the asymmetric centers of the acylamino, moiety, and resulted in identification of a non-competitive inhibitor with the same level of inhibitory activity of schyphostatin, the most potent of the few known small molecular inhibitors of sphingomyelinase. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00888-0
• 作为产物：
  描述：

  (1S,2S)-(+)-2-氨基-1-苯基-1,3-丙二醇 在 咪唑 、 偶氮二甲酸二异丙酯 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成 tert-butyl (1S,2R)-1-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-hydroxy-2-phenylethylcarbamate
  参考文献：
  名称：

  Synthesis of non-competitive inhibitors of Sphingomyelinases with significant activity

  摘要：

  A series of short-chain analogues of N-palmitoylsphingosine-1-phosphate, modified by replacement of the phosphate and the long alkenyl side chain with hydrolytically stable difluoromethylene phosphonate and phenyl, respectively, were prepared to study the structure-activity relationship for inhibition of sphingomyelinase. The study revealed that inhibition is highly dependent upon the stereochemistry of the asymmetric centers of the acylamino, moiety, and resulted in identification of a non-competitive inhibitor with the same level of inhibitory activity of schyphostatin, the most potent of the few known small molecular inhibitors of sphingomyelinase. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00888-0

文献信息

• Practical Synthesis of <i>threo</i>-(<i>S</i>,2<i>S</i>)- and <i>erythro</i>-(1<i>R</i>,2<i>S</i>)-1-Phenyl-2-palmitoylamino-3-morpholino-1-propanol (PPMP) from l-Serine
  作者：Atsushi Nishida、Hiroshi Sorimachi、Mie Iwaida、Miyako Matsumizu、Tomohiko Kawate、Masako Nakagawa

  DOI：10.1055/s-1998-3132

  日期：1998.4

  Both l-threo- and d-erythro-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol (PPMP) were synthesized stereoselectively from l-serine.

  L-苏型和 d-赤型-1-苯基-2-棕榈酰氨基-3-吗啉代-1-丙醇 (PPMP) 都是由 L-丝氨酸立体选择性合成的。
• Synthesis and evaluation of a difluoromethylene analogue of sphingomyelin as an inhibitor of sphingomyelinase
  作者：Tsutomu Yokomatsu、Hiroaki Takechi、Takeshi Akiyama、Shiroishi Shibuya、Takaaki Kominato、Shinji Soeda、Hiroshi Shimeno

  DOI：10.1016/s0960-894x(01)00179-2

  日期：2001.5

  A sphingomyelin analogue 2, in which the long alkenyl chain and the phosphodiester moiety of sphingomyelin were replaced by a phenyl and an isosteric difluoromethylenephosphonic acid, was prepared to evaluate its inhibitory potency to sphingomyelinase. The analogue non-competitively inhibited the neutral sphingomyelinase in bovine brain microsomes with an IC50 Of 400 muM. The compound had the ability to suppress tumor necrosis factor alpha -induced apoptosis of PC-12 neurons at a low concentration of 0.1 muM. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of non-competitive inhibitors of Sphingomyelinases with significant activity
  作者：Tsutomu Yokomatsu、Tetsuo Murano、Takeshi Akiyama、Junichi Koizumi、Shiroshi Shibuya、Yoshiaki Tsuji、Shinji Soeda、Hiroshi Shimeno

  DOI：10.1016/s0960-894x(02)00888-0

  日期：2003.1

  A series of short-chain analogues of N-palmitoylsphingosine-1-phosphate, modified by replacement of the phosphate and the long alkenyl side chain with hydrolytically stable difluoromethylene phosphonate and phenyl, respectively, were prepared to study the structure-activity relationship for inhibition of sphingomyelinase. The study revealed that inhibition is highly dependent upon the stereochemistry of the asymmetric centers of the acylamino, moiety, and resulted in identification of a non-competitive inhibitor with the same level of inhibitory activity of schyphostatin, the most potent of the few known small molecular inhibitors of sphingomyelinase. (C) 2002 Elsevier Science Ltd. All rights reserved.