(S,S)-2-<2--1-hydroxy-3-phenylpropyl>-1,3-thiazole | 124127-20-4

• 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: (S,S)-2-<2--1-hydroxy-3-phenylpropyl>-1,3-thiazole
• 英文别名: (1S)-2-Amino-2-N-(tert-butoxycarbonyl)-2,3-dideoxy-3-phenyl-1-(2-thiazolyl)-L-glycitol；2-<2(S)-(tert-Butoxyformamido)-1(S)-hydroxy-3-phenylpropyl>thiazole；tert-butyl N-[(1S,2S)-1-hydroxy-3-phenyl-1-(1,3-thiazol-2-yl)propan-2-yl]carbamate
• CAS: 124127-20-4
• 化学式: C₁₇H₂₂N₂O₃S
• 分子量: 334.439
• InChiKey: PDWROLFKWUGJEV-KBPBESRZSA-N

物化性质

• 沸点：
  509.2±50.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  99.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S,S)-2-<2--1-hydroxy-3-phenylpropyl>-1,3-thiazole 在 palladium on activated charcoal N-乙基吗啉 、 盐酸 、 sodium tetrahydroborate 、 3 A molecular sieve 、 氢气 、 sodium cyanoborohydride 、 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 乙腈 为溶剂， 反应 230.25h， 生成 沙喹那韦
  参考文献：
  名称：

  Studies toward the Large-Scale Synthesis of the HIV Proteinase Inhibitor Ro 31-8959

  摘要：

  Ro 31-8959 (1), a potent and selective inhibitor of HIV proteinase, is currently in phase III clinical trials. Six approaches for the large-scale synthesis of this compound have been studied. All routes employ an initial disconnection to an electrophilic L-phenylalanine homologue equivalent 13 and the decahydroisoquinoline derivative 5. They differ in adopting either an epoxide, a cyclic sulfate, or an aldehyde as the electrophilic entity and develop chirality from L-phenylalanine, dimethyl D-tartrate, or a Sharpless epoxidation. The preferred route starts from N-phthaloyl-L-phenylalaninyl chloride and uses tris((trimethylsilyl)oxy)ethene to effect homologation to hydroxy ketone 30, which is elaborated in a five-step two-pot procedure to N-phthaloyl epoxide 33 and hence 1. Kilogram quantities of Ro 31-8959 have been prepared using this route.

  DOI：

  10.1021/jo00092a026
• 作为产物：
  描述：

  2-<2(S)-(tert-Butoxyformamido)-1-hydroxy-3-phenylpropyl>thiazole 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 16.25h， 生成 (S,S)-2-<2--1-hydroxy-3-phenylpropyl>-1,3-thiazole
  参考文献：
  名称：

  Studies toward the Large-Scale Synthesis of the HIV Proteinase Inhibitor Ro 31-8959

  摘要：

  Ro 31-8959 (1), a potent and selective inhibitor of HIV proteinase, is currently in phase III clinical trials. Six approaches for the large-scale synthesis of this compound have been studied. All routes employ an initial disconnection to an electrophilic L-phenylalanine homologue equivalent 13 and the decahydroisoquinoline derivative 5. They differ in adopting either an epoxide, a cyclic sulfate, or an aldehyde as the electrophilic entity and develop chirality from L-phenylalanine, dimethyl D-tartrate, or a Sharpless epoxidation. The preferred route starts from N-phthaloyl-L-phenylalaninyl chloride and uses tris((trimethylsilyl)oxy)ethene to effect homologation to hydroxy ketone 30, which is elaborated in a five-step two-pot procedure to N-phthaloyl epoxide 33 and hence 1. Kilogram quantities of Ro 31-8959 have been prepared using this route.

  DOI：

  10.1021/jo00092a026

文献信息

• N-phosphinyl di-and tripeptides as renin inhibitors
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0376040A2

  公开（公告）日：1990-07-04

  The invention is new renin inhibitor dipeptide and tripeptide derivatives of the formula:

  本发明是新的肾素抑制剂二肽和三肽衍生物，其化学式为
• Chelation- and Non-chelation-Controlled Addition of 2-(Trimethylsilyl)thiazole to .alpha.-Amino Aldehydes: Stereoselective Synthesis of the .beta.-Amino-.alpha.-hydroxy Aldehyde Intermediate for the Preparation of the Human Immunodeficiency Virus Proteinase Inhibitor Ro 31-8959
  作者：Alessandro Dondoni、Daniela Perrone、Pedro Merino

  DOI：10.1021/jo00129a057

  日期：1995.12
• DONDONI, ALESSANDRO;FANTIN, GLIANCARLO;FOGAGNOLO, MARCO;PEDRINI, PAOLA, J. ORG. CHEM., 55,(1990) N, C. 1439-1446
  作者：DONDONI, ALESSANDRO、FANTIN, GLIANCARLO、FOGAGNOLO, MARCO、PEDRINI, PAOLA

  DOI：——

  日期：——
• Studies toward the Large-Scale Synthesis of the HIV Proteinase Inhibitor Ro 31-8959
  作者：Kevin E. B. Parkes、David J. Bushnell、Peter H. Crackett、Stephen J. Dunsdon、Andrew C. Freeman、Michelle P. Gunn、Richard A. Hopkins、Robert W. Lambert、Joseph A. Martin

  DOI：10.1021/jo00092a026

  日期：1994.7

  Ro 31-8959 (1), a potent and selective inhibitor of HIV proteinase, is currently in phase III clinical trials. Six approaches for the large-scale synthesis of this compound have been studied. All routes employ an initial disconnection to an electrophilic L-phenylalanine homologue equivalent 13 and the decahydroisoquinoline derivative 5. They differ in adopting either an epoxide, a cyclic sulfate, or an aldehyde as the electrophilic entity and develop chirality from L-phenylalanine, dimethyl D-tartrate, or a Sharpless epoxidation. The preferred route starts from N-phthaloyl-L-phenylalaninyl chloride and uses tris((trimethylsilyl)oxy)ethene to effect homologation to hydroxy ketone 30, which is elaborated in a five-step two-pot procedure to N-phthaloyl epoxide 33 and hence 1. Kilogram quantities of Ro 31-8959 have been prepared using this route.