TBSO-Hpp-OTBS | 89682-03-1

• 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: TBSO-Hpp-OTBS
• 英文别名: (1,1-dimethylethyl)dimethylsilyl (2S)-2-((1,1-dimethylethyl)dimethylsilyloxy)-3-phenylpropanoate；[tert-butyl(dimethyl)silyl] (2S)-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoate
• CAS: 89682-03-1
• 化学式: C₂₁H₃₈O₃Si₂
• 分子量: 394.702
• InChiKey: JFLMDZUHGCHDPN-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  TBSO-Hpp-OTBS 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-2-(tert-butyldimethylsilyloxy)-3-phenylpropanoyl chloride
  参考文献：
  名称：

  探测宿主选择性植物毒性：Phomalide，Isoophomalide和Dihydrophomalide的合成和生物活性。

  摘要：

  环状二肽肽苹果酸[cyclo（Val-（E）-Aba-Hpp-Hmp-（R）-Leu）；Aba = 2-氨基-2-丁烯酸，Hpp =（2S）-2-羟基-3-苯基丙酸，Hmp =（2S）-2-羟基-4-甲基戊酸]是由宿主产生的宿主选择性植物毒素真菌[Leptosphaeria maculans（Desm。）Ces。等人，无性阶段Phoma lingam（Tode ex Fr.）Desm。]引起黑腿病（几种经济上重要的芸苔属作物的毁灭性疾病）。描述了高效的磷丙二烯，其（Z）-异构体异麦芽酮酯和两种二氢类似物[（R）-二氢苹果酸和（S）-二氢苹果酸]的合成。Cbz-Val-（Z）-Aba与Hpp-Hmp-D-Leu-OBn的[2 + 3]片段偶联，然后去保护和环化，得到异麦考麦德，通过共轭添加PhSeH，然后消除对映体，将其非对映异构体异构化为磷酰亚胺。相应的亚硒酸盐。类似地使用Cbz-Val-

  DOI：

  10.1021/jo982376p
• 作为产物：
  描述：

  L-(-)-3-苯基乳酸 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 以87%的产率得到TBSO-Hpp-OTBS
  参考文献：
  名称：

  探测宿主选择性植物毒性：Phomalide，Isoophomalide和Dihydrophomalide的合成和生物活性。

  摘要：

  环状二肽肽苹果酸[cyclo（Val-（E）-Aba-Hpp-Hmp-（R）-Leu）；Aba = 2-氨基-2-丁烯酸，Hpp =（2S）-2-羟基-3-苯基丙酸，Hmp =（2S）-2-羟基-4-甲基戊酸]是由宿主产生的宿主选择性植物毒素真菌[Leptosphaeria maculans（Desm。）Ces。等人，无性阶段Phoma lingam（Tode ex Fr.）Desm。]引起黑腿病（几种经济上重要的芸苔属作物的毁灭性疾病）。描述了高效的磷丙二烯，其（Z）-异构体异麦芽酮酯和两种二氢类似物[（R）-二氢苹果酸和（S）-二氢苹果酸]的合成。Cbz-Val-（Z）-Aba与Hpp-Hmp-D-Leu-OBn的[2 + 3]片段偶联，然后去保护和环化，得到异麦考麦德，通过共轭添加PhSeH，然后消除对映体，将其非对映异构体异构化为磷酰亚胺。相应的亚硒酸盐。类似地使用Cbz-Val-

  DOI：

  10.1021/jo982376p

文献信息

• Probing Host-Selective Phytotoxicity:  Synthesis and Biological Activity of Phomalide, Isophomalide, and Dihydrophomalide
  作者：Dale E. Ward、Alfredo Vázquez、M. Soledade C. Pedras

  DOI：10.1021/jo982376p

  日期：1999.3.1

  anoic acid] is the host-selective phytotoxin produced by the fungus [Leptosphaeria maculans (Desm.) Ces. et de Not., asexual stage Phoma lingam (Tode ex Fr.) Desm.] which causes blackleg disease (a devastating disease of several economically important brassica crops). Efficient total syntheses of phomalide, its (Z)-isomer isophomalide, and the two dihydro analogues [(R)-dihydrophomalide and (S)-dihydrophomalide]

  环状二肽肽苹果酸[cyclo（Val-（E）-Aba-Hpp-Hmp-（R）-Leu）；Aba = 2-氨基-2-丁烯酸，Hpp =（2S）-2-羟基-3-苯基丙酸，Hmp =（2S）-2-羟基-4-甲基戊酸]是由宿主产生的宿主选择性植物毒素真菌[Leptosphaeria maculans（Desm。）Ces。等人，无性阶段Phoma lingam（Tode ex Fr.）Desm。]引起黑腿病（几种经济上重要的芸苔属作物的毁灭性疾病）。描述了高效的磷丙二烯，其（Z）-异构体异麦芽酮酯和两种二氢类似物[（R）-二氢苹果酸和（S）-二氢苹果酸]的合成。Cbz-Val-（Z）-Aba与Hpp-Hmp-D-Leu-OBn的[2 + 3]片段偶联，然后去保护和环化，得到异麦考麦德，通过共轭添加PhSeH，然后消除对映体，将其非对映异构体异构化为磷酰亚胺。相应的亚硒酸盐。类似地使用Cbz-Val-
• Process for the production of (S)-vinyl and allenyl gaba
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05208345A1

  公开（公告）日：1993-05-04

  The present invention is directed to a new class of pyrrolidinone derivatives that are useful as chemical intermediates in the synthesis of S-allenyl and S-vinyl GABA, both of which are antiepileptic agents.

  本发明涉及一种新型吡咯烷酮衍生物类，可作为化学中间体用于合成S-烯丙基GABA和S-乙烯基GABA，这两者都是抗癫痫药物。
• Transition State Analogy of Phosphonic Acid Peptide Inhibitors of Pepsin
  作者：Paul A. Bartlett、Mark A. Giangiordano

  DOI：10.1021/jo952074c

  日期：1996.1.1

  A series of 11 phosphonate peptide analogs, RO(2)C-Xaa-Yaa-Phe-(PO2--O)-Phe O-(3-(4-pyridyl)propyl ester), were synthesized and evaluated as inhibitors of the aspartic peptidase pepsin. For the inhibitors with Gly or Ala at the P-2 position, the K-i values correlate with the K-m/k(cat) values of the corresponding substrates, demonstrating that these analogs mimic the transition state in the way the P-2-P-4 residues bind. Deviations from the correlation for the other inhibitor/substrate pairs imply a different binding orientation as a result of N-substitution at P-2 (Pro), contamination with the more potent diastereomer (D-Ala), or a change in rate-limiting step for turnover (lie).
• Serendipitous Discovery of α-Hydroxyalkyl Esters as β-Lactamase Substrates
  作者：Ryan B. Pelto、R. F. Pratt

  DOI：10.1021/bi101071r

  日期：2010.12.14

  O-(1-Carboxy-1-alkyloxycarbonyl) hydroxamates were found to spontaneously decarboxylate in aqueous neutral buffer to form O-(2-hydroxyalkylcarbonyl) hydroxamates, While the former molecules do not react rapidly with serine beta-lactamases, the latter are quite good substrates of representative class A and C, but not D, enzymes, and particularly of a class C enzyme. The enzymes catalyze hydrolysis of these compounds to a mixture of the alpha-hydroxy acid and hydroxamate. Analogous compounds containing aryloxy leaving groups rather that hydroxamates are also substrates. Structure-activity experiments showed that the alpha-hydroxyl group was required for any substantial substrate activity. Although both D- and L-alpha-hydroxy acid derivatives were substrates, the former were preferred. The response of the class C activity to pH and to alternative nucleophiles (methanol and D-phenylalanine) suggested that the same active site functional groups participated in catalysis as for classical substrates. Molecular modeling was employed to explore how the alpha-hydroxy group might interact with the class C beta-lactamase active site. Incorporation of the alpha-hydroxyalkyl moiety into novel inhibitors will be of considerable interest.