N-FMOC-L-苏氨酸OBO酯 | 148150-71-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N-FMOC-L-苏氨酸OBO酯
• 英文名称: 1-[N-(9-fluorenylmethyloxycarbonyl)-(1S,2R)-1-amino-2-hydroxypropyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane
• 英文别名: N-Fmoc-L-threonine obo ester；9H-fluoren-9-ylmethyl N-[(1S,2R)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propyl]carbamate
• CAS: 148150-71-4
• 化学式: C₂₄H₂₇NO₆
• 分子量: 425.481
• InChiKey: BMIDOYRXNADNKK-RTQYLIPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-FMOC-L-苏氨酸OBO酯 在 Lindlar's catalyst 三(2-氯乙基)胺 、 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 1.0h， 生成 (2S,3S)-3-Amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 3-hydroxy-2-hydroxymethyl-2-methyl-propyl ester; hydrochloride
  参考文献：
  名称：

  Stereoselective Synthesis of β-Substituted α,β-Diamino Acids from β-Hydroxy Amino Acids

  摘要：

  DOI：

  10.1021/jo9904718
• 作为产物：
  描述：

  3-甲基-3-羟甲基氧杂环丁烷 在 4-二甲氨基吡啶 、 草酰氯 、 三氟化硼乙醚 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 11.29h， 生成 N-FMOC-L-苏氨酸OBO酯
  参考文献：
  名称：

  Blaskovich, Mark A.; Lajoie, Gilles A., Journal of the American Chemical Society, 1993, vol. 115, # 12, p. 5021 - 5030

  摘要：

  DOI：

文献信息

• Stereoselective synthesis of allo-threonine and β-2H-allo-threonine from threonine
  作者：Mark A. Blaskovich、Gilles A. Lajoie

  DOI：10.1016/s0040-4039(00)79241-0

  日期：1993.6

  Both D- and L-allo-threonine can be synthesized in good yield from D- and L-threonine respectively, by protection of the amine with Fmoc and the carboxyl with a cyclic ortho ester, followed by oxidation of the side chain to a ketone, and diastereoselective reduction to the allo isomer. Deprotection gives the amino acids in 40% overall yield. The beta-hydrogen can be labelled during reduction.
• Blaskovich, Mark A.; Lajoie, Gilles A., Journal of the American Chemical Society, 1993, vol. 115, # 12, p. 5021 - 5030
  作者：Blaskovich, Mark A.、Lajoie, Gilles A.

  DOI：——

  日期：——
• Stereoselective Synthesis of <i>Threo</i> and <i>Erythro</i> β-Hydroxy and β-Disubstituted-β-Hydroxy α-Amino Acids
  作者：Mark A. Blaskovich、Ghotas Evindar、Nicholas G. W. Rose、Scott Wilkinson、Yue Luo、Gilles A. Lajoie

  DOI：10.1021/jo972294l

  日期：1998.5.1

  Optically pure N-protected serine aldehyde equivalents can be prepared by the protection of the carboxylic group of serine by a cyclic ortho ester. Alkylation of N-Cbz-, N-Fmoc- or N-Boc-protected serine with oxetane tosylate 1 or bromide 2 gives the corresponding oxetane esters 4a-c which can easily be converted to the cyclic ortho esters 5a-c. A variety of unusual threo beta-hydroxy amino acids have been synthesized by Grignard addition to these optically pure serine aldehyde equivalents. The erythro diastereomers can be obtained by oxidation of the initial three adduct followed by reduction with LiBH4. Also described is a general approach for the diastereoselective synthesis of optically pure beta,beta-dialkyl-beta-hydroxy alpha-amino acids. These highly substituted amino acids are prepared by a sequence of Grignard addition to the optically active serine aldehyde equivalent, followed by oxidation of the initial adduct, and a second Grignard addition to the resulting ketone. The hydroxy adduct is obtained with very high diastereoselectivity (84-96% de). All four diastereomers can be selectively synthesized by varying the order of the Grignard additions and the chirality of the initial synthon. Removal of the protecting groups can be effected in very mild conditions, giving excellent yields of highly substituted amino acids in high diastereomeric purity.
• Stereoselective Synthesis of β-Substituted α,β-Diamino Acids from β-Hydroxy Amino Acids
  作者：Yue Luo、Mark A. Blaskovich、Gilles A. Lajoie

  DOI：10.1021/jo9904718

  日期：1999.8.1