(2R)-2-amino-3-[4-[[(1R,13S,16S,17R,28R)-28-amino-20-chloro-5,8,10,17,24-pentahydroxy-13-methoxycarbonyl-15,29,31-trioxo-22-oxa-14,30,32-triazahexacyclo[14.14.2.218,21.12,6.123,27.07,12]hexatriaconta-2(36),3,5,7(12),8,10,18,20,23,25,27(33),34-dodecaen-25-yl]oxy]-3-chlorophenyl]propanoic acid | 145007-42-7

• 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: (2R)-2-amino-3-[4-[[(1R,13S,16S,17R,28R)-28-amino-20-chloro-5,8,10,17,24-pentahydroxy-13-methoxycarbonyl-15,29,31-trioxo-22-oxa-14,30,32-triazahexacyclo[14.14.2.218,21.12,6.123,27.07,12]hexatriaconta-2(36),3,5,7(12),8,10,18,20,23,25,27(33),34-dodecaen-25-yl]oxy]-3-chlorophenyl]propanoic acid
• CAS: 145007-42-7
• 化学式: C₄₃H₃₇Cl₂N₅O₁₄
• 分子量: 918.698
• InChiKey: SDEFFAYAMNFOFI-HPVUEDHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  64
• 可旋转键数：
  7
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  323
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (2R)-2-amino-3-[4-[[(1R,13S,16S,17R,28R)-28-amino-20-chloro-5,8,10,17,24-pentahydroxy-13-methoxycarbonyl-15,29,31-trioxo-22-oxa-14,30,32-triazahexacyclo[14.14.2.218,21.12,6.123,27.07,12]hexatriaconta-2(36),3,5,7(12),8,10,18,20,23,25,27(33),34-dodecaen-25-yl]oxy]-3-chlorophenyl]propanoic acid 在 碳酸氢钠 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 9.08h， 生成 6,9-Etheno-4,19-(iminomethano)-11,15:20,24-dimetheno-1H-10,2,18-benzoxadiazacyclohexacosine-carboxylic acid, 13-(4-((2R)-2-carboxy-2-(((phenylmethoxy)carbonyl)amino)ethyl)-2-chlorophenoxy)-8-chloro-16-(((1,1-dimethylethoxy)carbonyl)amino)-2,3,4,5,16,17,18,19-octahydro-5,12,23,25,27-pentahydroxy-3,17,30-trioxo-, 1-methyl ester, (1S,4S,5R,16R,19R)-
  参考文献：
  名称：

  Structural Modifications of the Active Site in Teicoplanin and Related Glycopeptides. 2. Deglucoteicoplanin-Derived Tetrapeptide

  摘要：

  The deglucoteicoplanin-derived tetrapeptide (TDTP), a key synthon suitable for the synthesis of modified glycopeptide antibiotics differing in the structure of the active site, was prepared from the product (RH-TD) of reductive hydrolysis of the 2,3-peptide bond of deglucoteicoplanin (TD) upon selective oxidation of the newly formed hydroxymethyl group and following simultaneous removal of amino acids 1 and 3 by double Edman degradation. The oxidation of the alcohol function of residue 2 in RH-TD was accomplished (Jones reagent) after protection of the two free amino groups as tert-butyl BOC carbamates and of most of phenolic hydroxy groups as benzyl CBZ carbonates. Esterification of the C-terminal carboxy group of intermediate di-BOC-RH-TD allowed the formation at the end of the process of the tetrapeptide (TDTP-Me) protected at one carboxy group as methyl ester. Selective protection of the primary N-4- and N-2-amino groups of TDTP-Me as BOC and CBZ carbamates, respectively, followed by removal of the BOC function, afforded a more suitable intermediate (N-2-CBZ-TDTP-Me) for the synthesis of new glycopeptides.

  DOI：

  10.1021/jo9506746
• 作为产物：
  描述：

  (1S,2R,19R,22R,34S,37R,40R,52S)-22,34-diamino-5,15-dichloro-2,26,31,44,47,49,62-heptahydroxy-52-methoxycarbonyl-21,35,38,54,56-pentaoxo-7,13,28-trioxa-20,36,39,53,55-pentazadecacyclo[38.14.2.23,6.214,17.18,12.123,27.129,33.141,45.010,37.046,51]tetrahexaconta-3,5,8,10,12(62),14,16,23(59),24,26,29(58),30,32,41(57),42,44,46(51),47,49,60,63-henicosaene-19-carboxylic acid 在 硫代异氰酸苯酯 、 三氟乙酸 作用下， 生成 (2R)-2-amino-3-[4-[[(1R,13S,16S,17R,28R)-28-amino-20-chloro-5,8,10,17,24-pentahydroxy-13-methoxycarbonyl-15,29,31-trioxo-22-oxa-14,30,32-triazahexacyclo[14.14.2.218,21.12,6.123,27.07,12]hexatriaconta-2(36),3,5,7(12),8,10,18,20,23,25,27(33),34-dodecaen-25-yl]oxy]-3-chlorophenyl]propanoic acid
  参考文献：
  名称：

  Structural Modifications of the Active Site in Teicoplanin and Related Glycopeptides. 2. Deglucoteicoplanin-Derived Tetrapeptide

  摘要：

  The deglucoteicoplanin-derived tetrapeptide (TDTP), a key synthon suitable for the synthesis of modified glycopeptide antibiotics differing in the structure of the active site, was prepared from the product (RH-TD) of reductive hydrolysis of the 2,3-peptide bond of deglucoteicoplanin (TD) upon selective oxidation of the newly formed hydroxymethyl group and following simultaneous removal of amino acids 1 and 3 by double Edman degradation. The oxidation of the alcohol function of residue 2 in RH-TD was accomplished (Jones reagent) after protection of the two free amino groups as tert-butyl BOC carbamates and of most of phenolic hydroxy groups as benzyl CBZ carbonates. Esterification of the C-terminal carboxy group of intermediate di-BOC-RH-TD allowed the formation at the end of the process of the tetrapeptide (TDTP-Me) protected at one carboxy group as methyl ester. Selective protection of the primary N-4- and N-2-amino groups of TDTP-Me as BOC and CBZ carbamates, respectively, followed by removal of the BOC function, afforded a more suitable intermediate (N-2-CBZ-TDTP-Me) for the synthesis of new glycopeptides.

  DOI：

  10.1021/jo9506746

文献信息

• Structural Modifications of the Active Site in Teicoplanin and Related Glycopeptides. 2. Deglucoteicoplanin-Derived Tetrapeptide
  作者：Adriano Malabarba、Romeo Ciabatti、Michele Maggini、Pietro Ferrari、Luigi Colombo、Maurizio Denaro

  DOI：10.1021/jo9506746

  日期：1996.1.1

  The deglucoteicoplanin-derived tetrapeptide (TDTP), a key synthon suitable for the synthesis of modified glycopeptide antibiotics differing in the structure of the active site, was prepared from the product (RH-TD) of reductive hydrolysis of the 2,3-peptide bond of deglucoteicoplanin (TD) upon selective oxidation of the newly formed hydroxymethyl group and following simultaneous removal of amino acids 1 and 3 by double Edman degradation. The oxidation of the alcohol function of residue 2 in RH-TD was accomplished (Jones reagent) after protection of the two free amino groups as tert-butyl BOC carbamates and of most of phenolic hydroxy groups as benzyl CBZ carbonates. Esterification of the C-terminal carboxy group of intermediate di-BOC-RH-TD allowed the formation at the end of the process of the tetrapeptide (TDTP-Me) protected at one carboxy group as methyl ester. Selective protection of the primary N-4- and N-2-amino groups of TDTP-Me as BOC and CBZ carbamates, respectively, followed by removal of the BOC function, afforded a more suitable intermediate (N-2-CBZ-TDTP-Me) for the synthesis of new glycopeptides.