methyl (3S,4S)-3-butylamino-4,5-(isopropylidenedioxy)pentanoate | 87408-15-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (3S,4S)-3-butylamino-4,5-(isopropylidenedioxy)pentanoate
• 英文别名: methyl (3S)-3-(benzylamino)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate
• CAS: 87408-15-9
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: YPTKIFTZYUJJEX-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (3S,4S)-3-butylamino-4,5-(isopropylidenedioxy)pentanoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 methyl (3R)-3-[(tert-butoxycarbonyl)amino]-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate
  参考文献：
  名称：

  Stereoselective synthesis and preliminary evaluation of new d-3-heteroarylcarbonylalanines as ligands of the NMDA receptor

  摘要：

  New N-heteroarylcarbonylalanines of the D-series were stereoselectively prepared from enoates derived from D-mannitol. These compounds were active in binding and functional assays of the NMDA sub-type of glutamate receptors. A pyridine derivative inhibited MK801 binding, protected neurons from excitotoxic damage and blocked NMDA-induced currents in neurons. A thiophene derivative positively modulated the NMDA receptor, possibly through the allosteric glycine site. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.062
• 作为产物：
  描述：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 以 甲醇 为溶剂， 生成 methyl (3S,4S)-3-butylamino-4,5-(isopropylidenedioxy)pentanoate
  参考文献：
  名称：

  从D-甘油醛丙酮化物对映体选择性合成（R）-和（S）-4-[（甲氧羰基）-甲基] -2-氮杂环丁酮

  摘要：

  由苄基氨基酯对映选择性地合成（R）-N-苄基-4-[（甲氧基羰基）甲基] -2-氮杂环丁酮（10）和（S）-4-[（甲基羰基甲基）]-2-氮杂环丁酮（17）。如图3所示，其是通过将苄胺高度立体选择性地1，4-加成到衍生自D-甘油醛丙酮化物（1）的α，β-不饱和酯2上而制备的。

  DOI：

  10.1016/s0040-4039(00)88082-x

文献信息

• Enantioselective synthesis of (R)- and (S)-4-[(methoxycarbonyl)-methyl]-2-azetidinones from D-glyceraldehyde acetonide
  作者：Hiroshi Matsunaga、Tomoko Sakamaki、Hiroto Nagaoka、Yasuji Yamada

  DOI：10.1016/s0040-4039(00)88082-x

  日期：1983.1

  (R)-N-Benzyl-4-[(methoxycarbonyl)methyl]-2-azetidinone (10) and (S)-4-[(methylcarbonyl)methyl]-2-azetidinone (17) were enantioselectively synthesized from the benzylamino ester 3, which was prepared by the highly stereoselective 1,4-addition of benzylamine to the α,β-unsaturated ester 2 derived from D-glyceraldehyde acetonide (1).

  由苄基氨基酯对映选择性地合成（R）-N-苄基-4-[（甲氧基羰基）甲基] -2-氮杂环丁酮（10）和（S）-4-[（甲基羰基甲基）]-2-氮杂环丁酮（17）。如图3所示，其是通过将苄胺高度立体选择性地1，4-加成到衍生自D-甘油醛丙酮化物（1）的α，β-不饱和酯2上而制备的。
• Ketene silyl acetal chemistry; diastereofacial selectivity of 1,3-addition of chiral nitrones
  作者：Yasuyuki Kita、Osamu Tamura、Fumio Itoh、Hiroko Kishino、Takashi Miki、Masako Kohno、Yasumitsu Tamura

  DOI：10.1039/c39880000761

  日期：——

  The reaction of dimethyl-t-butylsiloxy-1-methoxyethene (1a) with the N-benzylnitrone (3a) produced the syn-1,3-adduct (4a) predominantly, while the reaction of dimethyl-t-butylsiloxy-1-t-butoxyethene (1b) with the N-diphenylmethylnitrone (3d) gave the anti-1,3-adduct (4h) predominantly; both adducts were readily transformed into the corresponding 3-benzoylamino-2,3-dideoxypentoses (8a,b) in fair yields

  二甲基叔丁基甲硅烷氧基-1-甲氧基乙烯（1a）与N-苄基硝基（3a）的反应主要产生合成-1,3-加合物（4a），而二甲基叔丁基甲硅烷氧基-1-t的反应-丁氧基乙烯（1b）与N-二苯基甲基硝基（3d）主要产生抗-1,3-加合物（4h）；两种加合物都容易以合理的产率转化为相应的3-苯甲酰基氨基-2，3-二脱氧戊糖（8a，b）。
• Synthesis of β-amino arylketones through the addition of ArLi derivatives to β-aminoesters
  作者：Paulo G Lima、Lucia C Sequeira、Paulo R.R Costa

  DOI：10.1016/s0040-4039(01)00358-6

  日期：2001.5

  2-Lithiumthiophene and 2-lithiumpyridine were allowed to react with iv-substituted beta -aminoesters. Only beta -amino arylketones were obtained from N-BOC, IV-H derivatives, while arylenoates were formed (retro-conjugate addition) from those substrates bearing N-Bn, N-H substituents, despite the aryllithium used. When the nitrogen is disubstituted (BOC and Bn), the product distribution depended on the nucleophile, leading to tertiary alcohols for 2-lithiumthiophene or ketones for 2-lithiumpyridine. Tertiary alcohols were also formed when PhLi was used as a nucleophile. (C) 2001 Elsevier Science Ltd. All rights reserved.
• KITA, YASUYUKI;TAMURA, OSAMU;ITOH, FUMIO;KISHINO, HIROKO;MIKI, TAKASHI;KO+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 2002-2007
  作者：KITA, YASUYUKI、TAMURA, OSAMU、ITOH, FUMIO、KISHINO, HIROKO、MIKI, TAKASHI、KO+

  DOI：——

  日期：——
• YAMADA, YASUJI
  作者：YAMADA, YASUJI

  DOI：——

  日期：——