(S)-N-tert-butoxycarbonyl-N,O-isopropylidene-α-methylserinal | 219567-00-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-N-tert-butoxycarbonyl-N,O-isopropylidene-α-methylserinal
• 英文别名: (S)-N-(tert-butoxycarbonyl)-4-formyl-2,2,4-trimethyl-3-oxazolidine；(S)-N-(tert-butoxycarbonyl)-4-formyl-2,2,4-trimethyloxazolidine；(S)-N-Boc-N,O-isopropylidene-α-methylserinal；N-Boc-N,O-isopropylidene-α-methylserinal；(S)-N-Boc-α-methylserinal acetonide；3-t-butoxycarbonyl-2,2-dimethyl-(4S)-formyl-4-methyloxazolidine；tert-butyl (4S)-4-formyl-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 219567-00-7
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: IDNHYCYNAKZHIC-GFCCVEGCSA-N

物化性质

• 熔点：
  54-55 °C
• 沸点：
  307.7±42.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-N-tert-butoxycarbonyl-N,O-isopropylidene-α-methylserinal 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 、 二氯乙基铝 、 boron trifluoride diacetate 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.08h， 生成 (4S,5S)-4-(hydroxymethyl)-4-methyl-5-phenyl-3-oxazolidin-2-one
  参考文献：
  名称：

  α-甲基-β-苯基丝氨酸的所有异构体的不对称合成

  摘要：

  该报告描述了对映体纯的（2 R，3 R）-，（2 R，3 S）-，（2 S，3 S）-和（2 S，3 R）-2-氨基-3-羟基的合成-2-甲基-3-苯基丙酸，四个季基α-氨基酸，采用立体发散性合成途径，从（S）-和（R）-N- Boc - N，O-异亚丙基-α-甲基丝氨酸开始。关键步骤涉及上述手性醛的不对称格利雅（Grignard）加成，其中观察到高水平的不对称诱导。

  DOI：

  10.1016/s0957-4166(00)00149-x
• 作为产物：
  描述：

  (1,3-二羟基-2-甲基-2-丙基)(2-甲基-2-丙基)氨基甲酸 在 sodium hydroxide 、 草酰氯 、 immobilized Pseudomonas sp. lipase 、 三氟化硼乙醚 、 四丁基氟化铵 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醚 为溶剂， 反应 3.0h， 生成 (S)-N-tert-butoxycarbonyl-N,O-isopropylidene-α-methylserinal
  参考文献：
  名称：

  Enzymatic desymmetrization of 2-amino-2-methyl-1,3-propanediol: asymmetric synthesis of (S)-N-Boc-N,O-isopropylidene-α-methylserinal and (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one

  摘要：

  We report herein, the novel enzymatic desymmetrization of 2-tert-butoxycarbonylamino-2-methyl-1,3-propanediol 1. This method makes it possible to prepare (S)-N-Boc-N,O-isopropylidene-alpha-methylserinal 3, which is a chiral building block for the synthesis of a variety of a-substituted alanine derivatives. Moreover, optically active (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one 4. one of the key intermediates in the synthesis of a novel immunosuppressant, has been prepared by this methodology. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.037

文献信息

• Amino alcohol derivatives
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20030236297A1

  公开（公告）日：2003-12-25

  Compounds of formula (I) which exhibit excellent immune suppression activity, pharmacologically acceptable salts thereof, esters thereof or other derivatives: 1 wherein R 1 and R 2 are a hydrogen atom, an amino protecting group; R 3 is a hydrogen atom, a hydroxy protecting group; R 4 is a lower alkyl group; n is an integer from 1 to 6; X is an ethylene group; Y is a C 1 -C 10 alkylene group, a C 1 -C 10 alkylene group substituted with 1 to 3 substituents selected from substituent group a and b; R 5 is an aryl group; R 6 and R 7 are a hydrogen atom, a group selected from substituent group a; with the proviso when R 5 is a hydrogen atom, Y is not a single bond or a straight chain C 1 -C 10 alkylene group.

  式（I）的化合物表现出优异的免疫抑制活性，其药理学上可接受的盐，酯或其他衍生物：其中R1和R2是氢原子，氨基保护基；R3是氢原子，羟基保护基；R4是较低的烷基基团；n是1到6之间的整数；X是乙烯基团；Y是C1-C10烷基基团，带有1到3个从取代基a和b中选择的取代基的C1-C10烷基基团；R5是芳基基团；R6和R7是氢原子，从取代基a中选择的基团；但是当R5是氢原子时，Y不是单键或直链的C1-C10烷基基团。
• Preparation and Synthetic Applications of (<i>S</i>)- and (<i>R</i>)-<i>N</i>-Boc-<i>N,O</i>-isopropylidene-α-methylserinals:  Asymmetric Synthesis of (<i>S</i>)- and (<i>R</i>)-2-Amino-2-methylbutanoic Acids (Iva)
  作者：Alberto Avenoza、Carlos Cativiela、Francisco Corzana、Jesús M. Peregrina、María M. Zurbano

  DOI：10.1021/jo990957o

  日期：1999.10.1

  describes an efficient and convenient large-scale synthesis procedure for (S)- and (R)-N-Boc-alpha-methylserinal acetonides (3 and 4) starting from (R)-2-methylglycidol 5. The application of both of these compounds as valuable chiral building blocks in the asymmetric synthesis of alpha-methylamino acids is also demonstrated by the synthesis of (S)- and (R)-isovalines (Iva) (6 and 7).

  该报告描述了从（R）-2-甲基缩水甘油5开始的（S）-和（R）-N-Boc-α-甲基丝氨酸丙酮化物（3和4）的高效便捷合成方法。 （S）-和（R）-异缬氨酸（Iva）的合成也证明了在α-甲基氨基酸的不对称合成中这些化合物作为有价值的手性结构单元（6和7）。
• 2-AMINOOXAZOLINES AS TAAR1 LIGANDS
  申请人：Galley Guido

  公开号：US20090105307A1

  公开（公告）日：2009-04-23

  The invention relates to compounds of formula wherein R 1 , R 2 , and R 3 are as defined herein and to a pharmaceutically suitable acid addition salts thereof for the treatment of CNS disorders.

  本发明涉及以下式子的化合物 其中R1，R2和R3如定义所述，并且其药物适宜的酸盐用于治疗中枢神经系统疾病。
• AMINO ALCOHOL DERIVATIVES
  申请人：Sankyo Company, Limited

  公开号：EP1300405B1

  公开（公告）日：2007-04-18
• Synthesis of (S)-N-tert-butoxycarbonyl-N,O-isopropylidene-α-methylserinal: A potential building block for the asymmetric synthesis of non-natural amino acids
  作者：Myriam Alías、Carlos Cativiela、María D. Díaz-de-Villegas、JoséA. Gálvez、Yolanda Lapeña

  DOI：10.1016/s0040-4020(98)00937-5

  日期：1998.12

  The title compound (S)-alpha-methylserinal acetonide has been efficiently prepared from (S)-alpha-methylserine, which is readily available in enantiomerically pure form by Curtius rearrangement of alpha,alpha-dialkyl 2-cyanoesters obtained by diastereoselective alkylation of (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate using methoxymethyl iodide or paraformaldehyde as electrophiles by an extension of our recently developed methodology for the synthesis of alpha,alpha-dialkylamino acids, (C) 1998 Elsevier Science Ltd. All rights reserved.