(2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-2-methyl-3-phenylpropionic acid methyl ester | 168416-37-3

• 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: (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-2-methyl-3-phenylpropionic acid methyl ester
• 英文别名: methyl (2R,3S)-2-hydroxy-2-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate
• CAS: 168416-37-3
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: ROQWEXIAGADABN-BLLLJJGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-2-methyl-3-phenylpropionic acid methyl ester 在 4-二甲氨基吡啶 、 lithium hydroxide 、 碳酸二(2-吡啶)酯 、 camphor-10-sulfonic acid 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 264.75h， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1-hydroxy-15-[(2R,3S)-2-hydroxy-2-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis(2,2,2-trichloroethoxycarbonyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Docetaxel (taxotere) derivatives: novel NbCl₃-based stereoselective approach to 2′-methyldocetaxel

  摘要：

  The C-2 methylated 2S,3R and 2R,3S side chains of docetaxel have been enantioselectively prepared and esterified with protected 10-deacetylbaccatin III to provide novel analogues of docetaxel.

  DOI：

  10.1039/p19950001811
• 作为产物：
  描述：

  benzaldehyde N-boc imine 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 4.42h， 生成 (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-2-methyl-3-phenylpropionic acid methyl ester
  参考文献：
  名称：

  Synthesis of Optically Active Constrained 2-Substituted Norstatines:  A Straightforward Application of Seebach's “SRS” Synthetic Principle

  摘要：

  A straightforward two-step methodology of synthesis of optically active (2,R)-substituted norstatines via addition of N-tert-butoxycarbonyl-substituted aldimines to (2S)-chiral enolates of 1,3-dioxolan-4-ones has been developed. In particular, the use of the natural (2S)-malic acid is examined for the synthesis of potential GABAergic spirocyclic gamma-lactams.

  DOI：

  10.1021/jo0486793

文献信息

• 1′-Azido- and 1′-amino-1,3-dioxolan-4-ones
  作者：Arturo Battaglia、Gaetano Barbaro、Patrizia Giorgianni、Andrea Guerrini、Antonella Pepe

  DOI：10.1016/s0957-4166(01)00173-2

  日期：2001.5

  1,3-Dioxolanone alcohols, prepared via the addition of chiral lithium enolates of 1,3-dioxolan-4-ones to aldehydes, are suitable intermediates for the synthesis of chiral trisubstituted isoserines or trisubstituted 3-hydroxy-β-lactams. In particular, the methyl ester of 2-methyl-3-(2-furyl)isoserinic acid and two 3-methyl-3-hydroxy-β-lactams bearing either a 2-furyl or a phenyl substituent at C-(4)

  通过将1，3-二氧戊环-4-酮的手性烯醇锂加成到醛中而制备的1，3-二氧戊环醇是合适的中间体，用于合成手性三取代的异丝氨酸或三取代的3-羟基-β-内酰胺。特别地，在C-（4）处带有2-呋喃基或苯基取代基的2-甲基-3-（2-呋喃基）异癸二酸甲酯和两个3-甲基-3-羟基-β-内酰胺具有准备好了。（2 - [R，3小号）异丝氨酸的立体化学，和（3 - [R，4小号的是必需的）两个β内酰胺类的立体化学为具有侧链与适当的（2'紫杉烷类似物的合成ř，3 'S）配置。
• Extremely stereoselective alkylation of 3-siloxy-β-lactams and its applications to the asymmetric syntheses of novel 2-alkylisoserines, their dipeptides, and taxoids
  作者：Iwao Ojima、Tao Wang、Francette Delaloge

  DOI：10.1016/s0040-4039(98)00643-1

  日期：1998.5

  New and efficient synthetic routes to 2-alkylisoserines, their dipeptides and 2′-alkyl-taxoids were synthesized from enantiopure 3-alkyl-β-lactams 3 which were obtained through extremely distereoselective alkylation of β-lactams 2.

  从对映体纯的3-烷基-β-内酰胺3合成了2-烷基异丝氨酸，其二肽和2'-烷基-类紫杉醇的新型有效合成路线，所述对映纯的3-烷基-β-内酰胺3是通过对β-内酰胺2的极度立体选择性烷基化而获得的。
• Docetaxel (taxotere) derivatives: novel NbCl₃-based stereoselective approach to 2′-methyldocetaxel
  作者：Jean-Noël Denis、Abdellatif Fkyerat、Yves Gimbert、Claire Coutterez、Pierre Mantellier、Sylvie Jost、Andrew E. Greene

  DOI：10.1039/p19950001811

  日期：——

  The C-2 methylated 2S,3R and 2R,3S side chains of docetaxel have been enantioselectively prepared and esterified with protected 10-deacetylbaccatin III to provide novel analogues of docetaxel.
• Synthesis of Optically Active Constrained 2-Substituted Norstatines:  A Straightforward Application of Seebach's “SRS” Synthetic Principle
  作者：Arturo Battaglia、Andrea Guerrini、Carlo Bertucci

  DOI：10.1021/jo0486793

  日期：2004.12.1

  A straightforward two-step methodology of synthesis of optically active (2,R)-substituted norstatines via addition of N-tert-butoxycarbonyl-substituted aldimines to (2S)-chiral enolates of 1,3-dioxolan-4-ones has been developed. In particular, the use of the natural (2S)-malic acid is examined for the synthesis of potential GABAergic spirocyclic gamma-lactams.