(1R,13S,16S,17R,28R)-28-amino-25-[4-[(2R)-2-amino-2-carboxyethyl]-2-chlorophenoxy]-20-chloro-5,8,10,17,24-pentahydroxy-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-dodecaene-13-carboxylic acid

• 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: (1R,13S,16S,17R,28R)-28-amino-25-[4-[(2R)-2-amino-2-carboxyethyl]-2-chlorophenoxy]-20-chloro-5,8,10,17,24-pentahydroxy-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-dodecaene-13-carboxylic acid
• 化学式: C₄₂H₃₅Cl₂N₅O₁₄
• 分子量: 904.671
• InChiKey: TWAOFKSTOLWPRZ-WCRSSAHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  63
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  334
• 氢给体数：
  12
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 反应 1.5h， 以100%的产率得到(1R,13S,16S,17R,28R)-28-amino-25-[4-[(2R)-2-amino-2-carboxyethyl]-2-chlorophenoxy]-20-chloro-5,8,10,17,24-pentahydroxy-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-dodecaene-13-carboxylic 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