(2R)-2-amino-3-[3-chloro-4-[[(1R,13S,16S,17R,28R)-20-chloro-5,8,10,17,24-pentahydroxy-13-methoxycarbonyl-28-[(2-methylpropan-2-yl)oxycarbonylamino]-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]phenyl]propanoic acid | 164515-55-3

• 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-[3-chloro-4-[[(1R,13S,16S,17R,28R)-20-chloro-5,8,10,17,24-pentahydroxy-13-methoxycarbonyl-28-[(2-methylpropan-2-yl)oxycarbonylamino]-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]phenyl]propanoic acid
• CAS: 164515-55-3
• 化学式: C₄₈H₄₅Cl₂N₅O₁₆
• 分子量: 1018.82
• InChiKey: QCYWYOFOHTWJOH-UQVOHKTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  71
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  335
• 氢给体数：
  11
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  (2R)-2-amino-3-[3-chloro-4-[[(1R,13S,16S,17R,28R)-20-chloro-5,8,10,17,24-pentahydroxy-13-methoxycarbonyl-28-[(2-methylpropan-2-yl)oxycarbonylamino]-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]phenyl]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 2.33h， 生成 Glycine, (2R)-2-(3-(4-((2R)-2-carboxy-2-(((phenylmethoxy)carbonyl)amino)ethyl)-2-chlorophenoxy)-4,5-dihydroxyphenyl)glycylglycyl-(betaR)-3-chloro-beta-hydroxy-L-tyrosyl-, 4-methyl ester, cyclic (15-34)-ether,cyclic 22,42-(4,6,6'-trihydroxy(1,1'-biphenyl)-3',2-diyl) deriv., (2(2R),4(2S))-
  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：

  在 三氟乙酸 作用下， 以50%的产率得到(2R)-2-amino-3-[3-chloro-4-[[(1R,13S,16S,17R,28R)-20-chloro-5,8,10,17,24-pentahydroxy-13-methoxycarbonyl-28-[(2-methylpropan-2-yl)oxycarbonylamino]-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]phenyl]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.