N-(benzyloxycarbonyl)-L-threonine methyl ester

• 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: N-(benzyloxycarbonyl)-L-threonine methyl ester
• 英文别名: Z-Thr-OMe；methyl (2S)-3-hydroxy-2-(phenylmethoxycarbonylamino)butanoate
• 化学式: C₁₃H₁₇NO₅
• 分子量: 267.282
• InChiKey: OPZWAOJFQFYYIX-UMJHXOGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)-L-threonine methyl ester 在 sodium hydride 、 氯磷酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以80%的产率得到methyl (2Z)-2-(N-benzyloxycarbonylamino)but-2-enoate
  参考文献：
  名称：

  One-step stereospecific synthesis of α,β-dehydroamino acids and dehydropeptides.

  摘要：

  Dehydroamino acids and dehydropeptides were prepared by a one-pot reaction employing diethyl chloroposphate in the presence of sodium hydride. The reaction is stereospecific and proceeds without racemization.

  DOI：

  10.1016/s0040-4039(00)74743-5

文献信息

• Copper‐Catalyzed Difluoromethylation of Alkyl Iodides Enabled by Aryl Radical Activation of Carbon–Iodine Bonds
  作者：Aijie Cai、Wenhao Yan、Chao Wang、Wei Liu

  DOI：10.1002/anie.202111993

  日期：2021.12.20

  An aryl radical activation strategy has been developed that can engage unactivated alkyl iodides in copper-catalyzed Negishi-type cross-coupling reactions. The strategy is based on the largely overlooked yet highly efficient reactivity of aryl radicals to abstract iodine atoms from alkyl iodides.

  已经开发出一种芳基自由基活化策略，可以在铜催化的 Negishi 型交叉偶联反应中使用未活化的烷基碘。该策略基于芳基自由基从烷基碘化物中提取碘原子的很大程度上被忽视但高效的反应性。
• Antineoplastic Agents. 561. Total Synthesis of Respirantin^1a
  作者：George R. Pettit、Thomas H. Smith、Song Feng、John C. Knight、Rui Tan、Robin K. Pettit、Peter A. Hinrichs

  DOI：10.1021/np0680735

  日期：2007.7.1

  Total synthesis of the 18-membered ring cyclodepsipeptide believed to be respirantin (1b) has been achieved. The key step in the synthesis is an intramolecular transesterification of the beta-ketoester alcohol 6 to afford the protected macrocycle 5. The synthetic product was shown to be identical to a natural product presumed to be respirantin (1b), and the absolute stereochemistry of six of the seven

  已实现了据信是respirantin（1b）的18元环环二肽的全合成。合成的关键步骤是将β-酮酸酯醇6进行分子内酯交换，以提供受保护的大环5。合成产物显示与假定为respirantin（1b）的天然产物相同，并且绝对立体化学为6环二肽1b的七个不对称中心明确建立。发现Respirantin（1b）是癌细胞生长的显着抑制剂，与抗生素的抗霉素家族有关。
• Organocatalytic Phosphorylation of Alcohols Using Pyridine-N-oxide
  作者：Alan Spivey、James Murray、Rudiger Woscholski

  DOI：10.1055/s-0034-1379993

  日期：——

  Phosphorylation of alcohols by phosphoryl chlorides catalysed by pyridine-N-oxide is reported. The utility of this method is demonstrated through phosphorylation of primary, secondary and a tertiary alcohol as well as phenols under mild reaction conditions and with low catalyst loading (5 mol%).
• The synthesis of derivatives of 3-O-(2-acetamido-2-deoxy-α-d-galacto-pyranosyl)-L-serine and-L-threonine
  作者：Bernard Ferrari、André A. Paviat

  DOI：10.1016/s0008-6215(00)85142-3

  日期：1980.2
• [EN] SYNTHESIS OF CYCLODEPSIPEPTIDE COMPOUNDS HAVING ANTINEOPLASTIC AND/OR ANTIMICROBIAL ACTIVITY<br/>[FR] SYNTHÈSE DE COMPOSÉS CYCLODEPSIPEPTIDE AYANT UNE ACTIVITÉ ANTINÉOPLASIQUE ET/OU ANTIMICROBIENNE
  申请人：UNIV ARIZONA

  公开号：WO2008151306A1

  公开（公告）日：2008-12-11

  [EN] The present invention is directed to effective methods of synthesizing cyclodepsipeptide compounds having antineoplastic and/or antimicrobial activity. Total syntheses of the eighteen-membered ring cyclodepsipeptides kitastatin (1a) and respirantin (1b) are taught. One important step in the synthesis is an intramolecular transesterification of the ?-ketoester alcohol 6 to afford the protected macrocycle 5. The synthetic products were shown to be identical to the natural products and the absolute stereochemistry of 6 of the 7 asymmetric centers of cyclodepsipeptide 1b was unequivocally established. Kitastatin (1a) and respirantin (1b) were found to be remarkable inhibitors of cancer cell growth and are related to the antimycin family of antibiotics.
  [FR] La présente invention concerne des procédés efficaces de synthèse de composés cyclodepsipeptide ayant une activité antinéoplasique et/ou antimicrobienne. Les synthèses totales des cyclodepsipeptides cycliques à dix-huit chaînons kitastatine (1a) et respirantine (1b) sont apprises. Une étape importante de la synthèse est une transestérification intramoléculaire de l'alcool cétoester 6 pour permettre le macrocycle protégé 5. Les produits de synthèse se sont avérés être identiques aux produits naturels et la stéréochimie absolue de 6 des 7 centres asymétriques de cyclodepsipeptide 1b a été établie de manière univoque. La kitatastine (1a) et la respirantine (1b) se sont avérées être des inhibiteurs remarquables de la croissance de cellules cancérigènes et sont liées à la famille antimycine d'antibiotiques.