Cbz-N-MeThr(TBS)-OH | 868151-77-3

• 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: Cbz-N-MeThr(TBS)-OH
• 英文别名: (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[methyl(phenylmethoxycarbonyl)amino]butanoic acid
• CAS: 868151-77-3
• 化学式: C₁₉H₃₁NO₅Si
• 分子量: 381.544
• InChiKey: DXZYATAWXLQBIM-ZBFHGGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Cbz-N-MeThr(TBS)-OH 在 palladium on activated charcoal 氢氟酸 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 (S)-1-[(2R,3R)-2-((2S,3R)-3-Hydroxy-2-methylamino-butyrylamino)-3-(4-hydroxy-phenyl)-3-methoxy-propionyl]-piperidine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of tripeptide hydrolysate from papuamide A: determination of absolute stereostructure of β-methoxytyrosine

  摘要：

  Four diastereomers, (2R 3R), (2S 3S), (2S,3R) and (2R,3S) at beta-methoxytyrosine (beta-OMeTyr), of the tripeptide hydrolysate, H-(S)-N-MeThr-beta-OMeTyr-(S)-Hpr-OH, from papuamide A have been synthesized. Comparison of the H-1 NMR data of the natural hydrolysate with the four synthetic diastereomers unambiguously establishes the relative and absolute stereochemistry of the methoxytyrosine as 2R,3R. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.023
• 作为产物：
  描述：

  benzyl (4S)-4-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-5-oxo-1,3-oxazolidine-3-carboxylate 在 三乙基硅烷 作用下， 以 氯仿 、 三氟乙酸 为溶剂， 以92%的产率得到Cbz-N-MeThr(TBS)-OH
  参考文献：
  名称：

  Synthesis of N-protected N-methyl serine and threonine

  摘要：

  Two efficient and convenient synthesis of N-Cbz and N-Fmoc N-methyl serine and threonine an described. The amino acid side-chain alcohol can be protected as a TBDMS ether in very good yield or left free, followed by the formation and subsequent reduction of the corresponding oxazolidinone. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)00606-2

文献信息

• Total Synthesis and Structural Determination of Cyclodepsipeptide Decatransin
  作者：Kosuke Ohsawa、Sakiko Fukaya、Takayuki Doi

  DOI：10.1021/acs.orglett.2c02085

  日期：2022.8.5

  determination of the 30-membered cyclodepsipeptide decatransin was demonstrated on the basis of total synthesis. Both (R)- and (S)-2-hydroxy-5-methylhexanoic acid derivatives were prepared via the Evans asymmetric alkylation. N-Alkyl-enriched peptide fragments were synthesized by the Cbz strategy in the solution phase without formation of diketopiperazine and epimerization. The synthesis of putative candidates

  在全合成的基础上，证明了 30 元环肽十肽的结构测定。( R )-和( S )-2-羟基-5-甲基己酸衍生物均通过Evans不对称烷基化制备。在溶液相中通过 Cbz 策略合成了富含N-烷基的肽片段，没有形成二酮哌嗪和差向异构化。推定候选物的合成是通过三个肽片段的会聚肽偶联，然后在光信条件下进行大环化来实现的。
• Synthesis of N-protected N-methyl serine and threonine
  作者：Yue Luo、Ghotas Evindar、Dan Fishlock、Gilles A Lajoie

  DOI：10.1016/s0040-4039(01)00606-2

  日期：2001.6

  Two efficient and convenient synthesis of N-Cbz and N-Fmoc N-methyl serine and threonine an described. The amino acid side-chain alcohol can be protected as a TBDMS ether in very good yield or left free, followed by the formation and subsequent reduction of the corresponding oxazolidinone. (C) 2001 Published by Elsevier Science Ltd.
• Synthesis of tripeptide hydrolysate from papuamide A: determination of absolute stereostructure of β-methoxytyrosine
  作者：Kazuishi Makino、Eri Nagata、Yasumasa Hamada

  DOI：10.1016/j.tetlet.2005.08.023

  日期：2005.10

  Four diastereomers, (2R 3R), (2S 3S), (2S,3R) and (2R,3S) at beta-methoxytyrosine (beta-OMeTyr), of the tripeptide hydrolysate, H-(S)-N-MeThr-beta-OMeTyr-(S)-Hpr-OH, from papuamide A have been synthesized. Comparison of the H-1 NMR data of the natural hydrolysate with the four synthetic diastereomers unambiguously establishes the relative and absolute stereochemistry of the methoxytyrosine as 2R,3R. (c) 2005 Elsevier Ltd. All rights reserved.