methyl (S)-2-[di(tert-butoxycarbonyl)amino]-6-oxohexanoate | 219617-15-9

• 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: methyl (S)-2-[di(tert-butoxycarbonyl)amino]-6-oxohexanoate
• 英文别名: methyl N,N-bis(tert-butyloxycarbonyl)-6-oxo-L-norleucinate；methyl (2S)-2-{(tert-butoxy)-N-[(tert-butyl)oxycarbonyl]carbonylamino}-7-oxohexanoate；methyl N,N-bis(tert-butoxycarbonyl)-6-oxo-L-norleucinate；methyl (2S)-2-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-6-oxohexanoate
• CAS: 219617-15-9
• 化学式: C₁₇H₂₉NO₇
• 分子量: 359.42
• InChiKey: AOYWWXNISBCHHB-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  99.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-[di(tert-butoxycarbonyl)amino]-6-oxohexanoate 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 sodium azide 、 L-(+)-酒石酸二乙酯 、 二异丁基氢化铝 、 氯化铵 作用下， 以 甲醇 、 异辛烷 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 28.08h， 生成 methyl (2S,6S,7S)-6-azido-2-tert-butoxycarbonylamino-7,8-dihydroxyoctanoate
  参考文献：
  名称：

  General Stereoselective Synthesis of Chemically Differentiated α-Diamino Acids:  Synthesis of 2,6-Diaminopimelic and 2,7-Diaminosuberic Acids

  摘要：

  DOI：

  10.1021/jo0155714
• 作为产物：
  描述：

  BOC-L-天冬氨酸二甲酯 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 乙酸乙酯 、 乙腈 、 苯 为溶剂， 反应 0.16h， 生成 methyl (S)-2-[di(tert-butoxycarbonyl)amino]-6-oxohexanoate
  参考文献：
  名称：

  Enantiospecific synthesis of α-amino acid semialdehydes: a key step for the synthesis of unnatural unsaturated and saturated α-amino acids

  摘要：

  The enantiospecific synthesis of unnatural unsaturated and saturated alpha-amino acids based on a Wittig type reaction is described. The versatile synthetic intermediates, L-glutamic and L-aspartic acid semialdehydes, are obtained from the corresponding N,N-di-Boc-diesters, by the selective reduction of the omega'-ester with DIBAL(R) under controlled conditions. The semialdehydes are chemically stable for a prolonged time and react with various phosphorous ylides, under controlled conditions, to produce the enantiomerically pure unsaturated alpha-amino acids in high yields. The method is equally applicable to homologated diesters obtained by the presented methodology providing unsaturated amino acids with variable unsaturated positions and geometries. The corresponding saturated products can be obtained by simple hydrogenation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00354-1

文献信息

• [EN] HIV PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PROTÉASE DU VIH
  申请人：MERCK CANADA INC

  公开号：WO2012055031A1

  公开（公告）日：2012-05-03

  Compounds of Formula I are disclosed wherein R1, R2, R3A, R3B, R4A, R4B, R5A, R5B, R6A, R6B, R7, R8 and R9 are defined herein. The compounds encompassed by Formula I include compounds which are HIV protease inhibitors and other compounds which can be metabolized in vivo to HIV protease inhibitors. The compounds and their pharmaceutically acceptable salts are useful for the prophylaxis or treatment of infection by HIV and the prophylaxis, treatment, or delay in the onset of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

  公式I的化合物被披露，其中R1、R2、R3A、R3B、R4A、R4B、R5A、R5B、R6A、R6B、R7、R8和R9在此有定义。公式I包括HIV蛋白酶抑制剂和其他可以在体内代谢成HIV蛋白酶抑制剂的化合物。这些化合物及其药用盐对于预防或治疗HIV感染以及预防、治疗或延缓艾滋病的发作很有用。这些化合物及其盐可作为药物组成部分，可选择性地与其他抗病毒药物、免疫调节剂、抗生素或疫苗组合使用。
• HIV protease inhibitors
  申请人：Boyd Michael John

  公开号：US09079834B2

  公开（公告）日：2015-07-14

  Compounds of Formula I are disclosed wherein R1, R2, R3A, R3B, R4A, R4B, R5A, R5B, R6A, R6B, R7, R8 and R9 are defined herein. The compounds encompassed by Formula I include compounds which are HIV protease inhibitors and other compounds which can be metabolized in vivo to HIV protease inhibitors. The compounds and their pharmaceutically acceptable salts are useful for the prophylaxis or treatment of infection by HIV and the prophylaxis, treatment, or delay in the onset of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

  公式I的化合物被披露，其中R1、R2、R3A、R3B、R4A、R4B、R5A、R5B、R6A、R6B、R7、R8和R9在此被定义。公式I所包含的化合物包括HIV蛋白酶抑制剂和可以在体内代谢成HIV蛋白酶抑制剂的其他化合物。这些化合物及其药学上可接受的盐对于预防或治疗HIV感染以及预防、治疗或延缓艾滋病的发作非常有用。这些化合物及其盐可以作为药物组成部分，可以选择与其他抗病毒药物、免疫调节剂、抗生素或疫苗组合使用。
• HIV PROTEASE INHIBITORS
  申请人：Boyd Michael John

  公开号：US20140018325A1

  公开（公告）日：2014-01-16

  Compounds of Formula I are disclosed wherein R 1 , R 2 , R 3A , R 3B , R 4A , R 4B , R 5A , R 5B , R 6A , R 6B , R 8 and R 9 are defined herein. The compounds encompassed by Formula I include compounds which are HIV protease inhibitors and other compounds which can be metabolized in vivo to HIV protease inhibitors. The compounds and their pharmaceutically acceptable salts are useful for the prophylaxis or treatment of infection by HIV and the prophylaxis, treatment, or delay in the onset of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

  公式I的化合物已经被披露，其中R1、R2、R3A、R3B、R4A、R4B、R5A、R5B、R6A、R6B、R8和R9在此定义。公式I所包含的化合物包括HIV蛋白酶抑制剂和其他可以在体内代谢成HIV蛋白酶抑制剂的化合物。这些化合物及其药学上可接受的盐可用于预防或治疗HIV感染以及预防、治疗或延迟艾滋病的发病。这些化合物及其盐可作为制药组合物的成分，可选择与其他抗病毒药物、免疫调节剂、抗生素或疫苗组合使用。
• Synthesis and inhibitory activity of substrate-analog fructosyl peptide oxidase inhibitors
  作者：Bunta Watanabe、Atsushi Ichiyanagi、Kozo Hirokawa、Keiko Gomi、Toru Nakatsu、Hiroaki Kato、Naoki Kajiyama

  DOI：10.1016/j.bmcl.2015.07.045

  日期：2015.9

  Fructosyl peptide oxidases (FPOXs) play a crucial role in the diagnosis of diabetes. Their main function is to cleave fructosyl amino acids or fructosyl peptides into glucosone and the corresponding amino acids/dipeptides. In this study, the substrate-analog FPOX inhibitors 1a-c were successfully designed and synthesized. These inhibitors mimic N-alpha-fructosyl-L-valine (Fru-Val), [N-alpha-fructosyl-L-valyl]-L-histidine (Fru-ValHis), and N-epsilon-fructosyl-L-lysine (epsilon Fru-Lys), respectively. The secondary nitrogen atom in the natural substrates, linking fructose and amino acid or dipeptide moieties, was substituted in 1a-c with a sulfur atom to avoid enzymatic cleavage. Kinetic studies revealed that 1a-c act as competitive inhibitors against an FPOX obtained from Coniochaeta sp., and K-i values of 11.1, 66.8, and 782 mu M were obtained for 1a-c, respectively. (C) 2015 Elsevier Ltd. All rights reserved.
• US9079834B2
  申请人：——

  公开号：US9079834B2

  公开（公告）日：2015-07-14