tert-butyl (4S,5R)-4-hydroxymethyl-2,2-dimethyl-5-phenyl-1,3-oxazolidin-3-carboxylate | 350503-45-6

• 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: tert-butyl (4S,5R)-4-hydroxymethyl-2,2-dimethyl-5-phenyl-1,3-oxazolidin-3-carboxylate
• 英文别名: tert-butyl (4S,5R)-4-(hydroxymethyl)-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate
• CAS: 350503-45-6
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: LBTFCAQHUDISGT-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S,5R)-4-hydroxymethyl-2,2-dimethyl-5-phenyl-1,3-oxazolidin-3-carboxylate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 (4R,5R)-4-Formyl-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and evaluation of a difluoromethylene analogue of sphingomyelin as an inhibitor of sphingomyelinase

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(01)00179-2
• 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 、 四丁基氟化铵 、 二异丁基氢化铝 、 对甲苯磺酸 、 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 、 苯 为溶剂， 反应 33.0h， 生成 tert-butyl (4S,5R)-4-hydroxymethyl-2,2-dimethyl-5-phenyl-1,3-oxazolidin-3-carboxylate
  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

• Highly enantioselective synthesis of anti aryl β-hydroxy α-amino esters via DKR transfer hydrogenation
  作者：Zhuqing Liu、C.Scott Shultz、Candice A. Sherwood、Shane Krska、Peter G. Dormer、Richard Desmond、Claire Lee、Edward C. Sherer、Joseph Shpungin、James Cuff、Feng Xu

  DOI：10.1016/j.tetlet.2011.01.146

  日期：2011.4

  aryl β-hydroxy α-amino esters via dynamic kinetic resolution (DKR), asymmetric transfer hydrogenation of α-amino β-keto esters is described. The anti β-hydroxyl α-amino esters were obtained both in high yields and high diasteroselectivity. The observed high anti selectivity is inconsistent with the previous results in literature. The absolute stereochemistry of the aryl β-hydroxy α-amino esters was

  描述了通过动态动力学拆分（DKR），α-氨基β-酮酯的不对称转移氢化有效制备高度对映体富集的芳基β-羟基α-氨基酯的方法。的抗β-α羟基氨基酯进行以高产率和高diasteroselectivity获得两者。观察到的高抗选择性与文献中先前的结果不一致。芳基β-羟基α-氨基酯的绝对立体化学通过化学衍生化和振动圆二色性（VCD）技术得到明确证实。
• 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.