O-tert-butyldiphenylsilyl-L-threonine methyl ester | 148205-40-7

• 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: O-tert-butyldiphenylsilyl-L-threonine methyl ester
• 英文别名: methyl (2S,3R)-2-amino-3-[tert-butyl(diphenyl)silyl]oxybutanoate
• CAS: 148205-40-7
• 化学式: C₂₁H₂₉NO₃Si
• 分子量: 371.552
• InChiKey: FXKJJLARAQPLMG-APWZRJJASA-N

物化性质

• 沸点：
  427.7±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-tert-butyldiphenylsilyl-L-threonine methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 40.0h， 生成 methyl (2S,3R)-2-[[(2S)-2-amino-2-[(4S,5S)-5-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]acetyl]amino]-3-[tert-butyl(diphenyl)silyl]oxybutanoate
  参考文献：
  名称：

  A Strategy for the Asymmetric Aminohomologation of α,β-Dihydroxy Aldehydes:  Application to the Synthesis of the Southwest Tripeptide Segment of Echinocandin B

  摘要：

  The synthesis of the (2S,3S,4S)-3,4-dihydroxyhomotyrosine amino acid segment, present in echinocandin B, in its activated form ready for peptide coupling is described. The key steps of the approach are the enantioselective AD reaction of 4-methoxycinnamic acid methyl ester, a completely diastereoselective [2 + 2] hydroxyketene-imine cycloaddition, and the TEMPO-assisted cyclo-expansion of the resulting 3-hydroxy beta-lactam to the corresponding alpha-amino acid N-carboxy anhydride (NCA). The smooth opening of the latter upon treatment with L-Thr((OSiBuPh2)-Bu-t)OMe and further acylation with the N-Cbz protected L-4-tert-butyldiphenylsilyloxy proline rendered the southwest portion of echinocandin B.

  DOI：

  10.1021/jo990964c
• 作为产物：
  描述：

  O-(tert-butyldiphenylsilyl)-L-threonine 在 palladium on activated charcoal 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 19.0h， 生成 O-tert-butyldiphenylsilyl-L-threonine methyl ester
  参考文献：
  名称：

  A Strategy for the Asymmetric Aminohomologation of α,β-Dihydroxy Aldehydes:  Application to the Synthesis of the Southwest Tripeptide Segment of Echinocandin B

  摘要：

  The synthesis of the (2S,3S,4S)-3,4-dihydroxyhomotyrosine amino acid segment, present in echinocandin B, in its activated form ready for peptide coupling is described. The key steps of the approach are the enantioselective AD reaction of 4-methoxycinnamic acid methyl ester, a completely diastereoselective [2 + 2] hydroxyketene-imine cycloaddition, and the TEMPO-assisted cyclo-expansion of the resulting 3-hydroxy beta-lactam to the corresponding alpha-amino acid N-carboxy anhydride (NCA). The smooth opening of the latter upon treatment with L-Thr((OSiBuPh2)-Bu-t)OMe and further acylation with the N-Cbz protected L-4-tert-butyldiphenylsilyloxy proline rendered the southwest portion of echinocandin B.

  DOI：

  10.1021/jo990964c

文献信息

• Asymmetric α-Allylation of α-Substituted β-Ketoesters with Allyl Alcohols
  作者：Masanori Yoshida

  DOI：10.1021/acs.joc.7b02188

  日期：2017.12.1

  Enantioselective α-allylation of α-substituted β-ketoesters with simple allyl alcohols was successfully performed by synergistic catalysis with the catalyst combination of a chiral primary amino acid and an achiral palladium complex without additional promotors like acids or bases. The allylation reaction and generation of a chiral quaternary carbon stereocenter proceeded smoothly to produce α,α-disubstituted

  α-取代的β-酮酸酯与简单的烯丙醇的对映选择性α-烯丙基化是通过手性伯氨基酸和非手性钯配合物的催化剂组合的协同催化成功进行的，而没有其他促进剂，例如酸或碱。烯丙基化反应和手性季碳立体中心的生成顺利进行，以高收率（91-99％）和高对映选择性（90-99％ee）生产出α，α-二取代的β-酮酸酯。
• New highly active taxoids from 9β-Dihydrobaccatin-9,10-acetals. Part 4
  作者：Yasuyuki Takeda、Kouichi Uoto、Jun Chiba、Takao Horiuchi、Michio Iwahana、Ryo Atsumi、Chiho Ono、Hirofumi Terasawa、Tsunehiko Soga

  DOI：10.1016/s0968-0896(03)00454-1

  日期：2003.10

  It was shown that a new taxane analogue 3, which exhibited both in vitro antitumor activity and in vivo efficacy by both iv and po administration, was prone to be metabolized by human liver microsomes. We identified a major metabolite, M-1. generated by human liver microsomes as 20a, a hydroxylated compound at the pyridine ring of 3. To improve the metabolic stability of 3, we designed and synthesized new taxane analogues based on the structure of M-1. and obtained some compounds that maintained excellent antitumor activity and were scarcely metabolized by human liver microsomes. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of (2R,3S) 3-amino-4-mercapto-2-butanol, a threonine analogue for covalent inhibition of sortases
  作者：Michael E. Jung、Jeremy J. Clemens、Nuttee Suree、Chu Kong Liew、Rosemarie Pilpa、Dean O. Campbell、Robert T. Clubb

  DOI：10.1016/j.bmcl.2005.07.073

  日期：2005.11

  L-Threonine 2 was converted in seven steps into the protected aminomercaptoalcohol 8, a threonine mimic. This compound 8 was coupled to various oligopeptides to produce two different tetrapeptide analogues, for example, 11 and 17, which were shown to inhibit the Sortase enzymes (SrtA and SrtB) via covalent attachment of the thiol groups of 11 and 17 to the catalytically active cysteine residue of the Sortase enzymes. (c) 2005 Elsevier Ltd. All rights reserved.