| 145007-46-1

• 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
• CAS: 145007-46-1
• 化学式: C₅₂H₅₃Cl₂N₅O₁₇
• 分子量: 1090.92
• InChiKey: YYDNJTJXAIXTSA-OEZCJBSLSA-N

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 1.5h， 以6.4 g的产率得到
  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-19-(hydroxymethyl)-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-52-carboxylic acid 在 碳酸氢钠 、 硫代异氰酸苯酯 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 15.5h， 生成
  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