2-<2(S)-(tert-Butoxyformamido)-1-hydroxy-3-phenylpropyl>thiazole | 219586-42-2

• 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: 2-<2(S)-(tert-Butoxyformamido)-1-hydroxy-3-phenylpropyl>thiazole
• 英文别名: (1RS,2S)-2-(tert-Butoxycarbonyl)amino-3-phenyl-1-(2-thiazolyl)-1-propanol；tert-butyl N-[(2S)-1-hydroxy-3-phenyl-1-(1,3-thiazol-2-yl)propan-2-yl]carbamate
• CAS: 219586-42-2
• 化学式: C₁₇H₂₂N₂O₃S
• 分子量: 334.439
• InChiKey: PDWROLFKWUGJEV-LSLKUGRBSA-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：

  2-<2(S)-(tert-Butoxyformamido)-1-hydroxy-3-phenylpropyl>thiazole 在 palladium on activated charcoal N-乙基吗啉 、 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 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 246.5h， 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：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-<2(S)-(tert-Butoxyformamido)-1-hydroxy-3-phenylpropyl>thiazole
  参考文献：
  名称：

  Stereochemistry associated with the addition of 2-(trimethylsilyl)thiazole to differentially protected .alpha.-amino aldehydes. Applications toward the synthesis of amino sugars and sphingosines

  摘要：

  DOI：

  10.1021/jo00292a013

文献信息

• A new method for the solid phase synthesis of hydroxyethylamine peptide bond isosteres : Synthesis of an HIV-1 protease inhibitor and of a β-casomorphin-5 analogue.
  作者：D. Tourwé、J. Piron、P. Defreyn、G. Van Binst

  DOI：10.1016/s0040-4039(00)73945-1

  日期：1993.1

  A solid phase synthesis procedure for the preparation of hydroxyethylamine peptide isosteres is describe. Reductive amination of the resin-bound peptide with an α-hydroxyaldehyde, prepared via 2-(trimethylsilyl) thiazole addition to Boc-phenylalaninal or Boc-prolinal, produces the peptides in good yield.

  描述了用于制备羟乙胺肽等排物的固相合成方法。通过将2-（三甲基甲硅烷基）噻唑加到Boc-苯丙氨酸或Boc-脯氨酸中制备的α-羟醛对树脂结合的肽进行还原性胺化反应，可以很好地产生肽。
• Grignard Addition to Aldonitrones. Stereochemical Aspects and Application to the Synthesis of C₂-Symmetric Diamino Alcohols and Diamino Diols
  作者：Alessandro Dondoni、Daniela Perrone、Marilisa Rinaldi

  DOI：10.1021/jo980980u

  日期：1998.12.1

  A new example of the stereoselective installation of the amino group at a saturated carbon center via organometallic addition of chiral aldehydes to nitrones is illustrated by the synthesis of 1,3-diamino propanol 1 and 1,4-diamino butandiol 2 units. Three diamino alcohol 1 stereotriads were obtained by stereoselective addition of alkylmagnesium halides (benzyl, cyclohexylmethyl, and metallyl) to the N-benzyl nitrones derived from beta-amino-alpha-hydroxy aldehydes followed by reduction of the resulting N-benzylhydroxylamines. Three 1,4-dibenzyl substituted stereoisomers of type 2 with fixed S configuration at C2 and C3 were prepared by sequential and simultaneous amination in two directions starting from L-threose nitrone and L-tartraldehyde bis-nitrone, respectively. The R,S,S,R isomer obtained by the former route was converted into a seven-membered ring cyclic urea (1,3-diazapin-2-one), i.e., a compound that belongs to a class of nonpeptide HIV-1 protease inhibitors.
• US6410576B1
  申请人：——

  公开号：US6410576B1

  公开（公告）日：2002-06-25
• US6713472B1
  申请人：——

  公开号：US6713472B1

  公开（公告）日：2004-03-30
• US6960575B2
  申请人：——

  公开号：US6960575B2

  公开（公告）日：2005-11-01