(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2,5-bis-{[((S)-3-methyl-1-methylcarbamoyl-butylcarbamoyl)-methyl]-carbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester | 419564-76-4

• 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,3R,4R,5R)-3,4-Bis-benzyloxy-2,5-bis-{[((S)-3-methyl-1-methylcarbamoyl-butylcarbamoyl)-methyl]-carbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2R,3R,4R,5R)-2,5-bis[[2-[[(2S)-4-methyl-1-(methylamino)-1-oxopentan-2-yl]amino]-2-oxoethyl]carbamoyl]-3,4-bis(phenylmethoxy)pyrrolidine-1-carboxylate
• CAS: 419564-76-4
• 化学式: C₄₃H₆₃N₇O₁₀
• 分子量: 838.014
• InChiKey: CXNBLYILRBOKJQ-PKJKPJGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  60
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  223
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2,5-bis-{[((S)-3-methyl-1-methylcarbamoyl-butylcarbamoyl)-methyl]-carbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester 在 20percent Pd(OH)2 on C 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以80%的产率得到(2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-{[((S)-3-methyl-1-methylcarbamoyl-butylcarbamoyl)-methyl]-carbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Studies on Novel Peptidomimetics Having Bi-directional Dispositions of Hydroxylated d-Pro-Gly Motifs Anchored on a C₂-Symmetric Iminosugar-Based Foundation

  摘要：

  A rigid pyrrolidine based scaffold comprising of 2,5-dideoxy-2,5-imino-D-idaric acid (1) is developed. Attachment of peptide strands to the carboxylic groups at both ends of this novel template led to the peptidomimetics 2 and 3. Conformational analysis by NMR studies revealed that compounds 2b, 3b and 2c, 3c take interesting turn structures (C-2 symmetric for 2c and 3c) in DMSO-d(6) consisting of identical intramolecular hydrogen bonds at two ends between LeuNH --> sugar-OH as depicted in structure A, whereas 2a and 3a display structures with regular beta-turns with hydrogen bonds between LeuNH --> Boc-C=O in one-half of their molecular frameworks (structure B), characteristic of the turn structures commonly observed in "D-Pro-Gly"-containing peptides. These results suggest that a cis hydroxyl group at the 3-position of the proline residue favors a pseudo,beta-turn-like nine-membered ring structure in hydroxyproline-containing peptides involving an intramolecular hydrogen bond between the hydroxyl and the i + 2 backbone amide.

  DOI：

  10.1021/jo010937y
• 作为产物：
  描述：

  1,3(R):4,6(R)-bis-O-(4-methoxybenzylidene)-D-mannitol 在 20percent Pd(OH₂) on C lithium aluminium tetrahydride 、 重铬酸吡啶 、 三氯化铝 、 氢气 、 sodium hydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.75h， 生成 (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2,5-bis-{[((S)-3-methyl-1-methylcarbamoyl-butylcarbamoyl)-methyl]-carbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Studies on Novel Peptidomimetics Having Bi-directional Dispositions of Hydroxylated d-Pro-Gly Motifs Anchored on a C₂-Symmetric Iminosugar-Based Foundation

  摘要：

  A rigid pyrrolidine based scaffold comprising of 2,5-dideoxy-2,5-imino-D-idaric acid (1) is developed. Attachment of peptide strands to the carboxylic groups at both ends of this novel template led to the peptidomimetics 2 and 3. Conformational analysis by NMR studies revealed that compounds 2b, 3b and 2c, 3c take interesting turn structures (C-2 symmetric for 2c and 3c) in DMSO-d(6) consisting of identical intramolecular hydrogen bonds at two ends between LeuNH --> sugar-OH as depicted in structure A, whereas 2a and 3a display structures with regular beta-turns with hydrogen bonds between LeuNH --> Boc-C=O in one-half of their molecular frameworks (structure B), characteristic of the turn structures commonly observed in "D-Pro-Gly"-containing peptides. These results suggest that a cis hydroxyl group at the 3-position of the proline residue favors a pseudo,beta-turn-like nine-membered ring structure in hydroxyproline-containing peptides involving an intramolecular hydrogen bond between the hydroxyl and the i + 2 backbone amide.

  DOI：

  10.1021/jo010937y

文献信息

• Studies on Novel Peptidomimetics Having Bi-directional Dispositions of Hydroxylated <scp>d</scp>-Pro-Gly Motifs Anchored on a <i>C</i>₂-Symmetric Iminosugar-Based Foundation
  作者：T. K. Chakraborty、P. Srinivasu、S. Kiran Kumar、A. C. Kunwar

  DOI：10.1021/jo010937y

  日期：2002.4.1

  A rigid pyrrolidine based scaffold comprising of 2,5-dideoxy-2,5-imino-D-idaric acid (1) is developed. Attachment of peptide strands to the carboxylic groups at both ends of this novel template led to the peptidomimetics 2 and 3. Conformational analysis by NMR studies revealed that compounds 2b, 3b and 2c, 3c take interesting turn structures (C-2 symmetric for 2c and 3c) in DMSO-d(6) consisting of identical intramolecular hydrogen bonds at two ends between LeuNH --> sugar-OH as depicted in structure A, whereas 2a and 3a display structures with regular beta-turns with hydrogen bonds between LeuNH --> Boc-C=O in one-half of their molecular frameworks (structure B), characteristic of the turn structures commonly observed in "D-Pro-Gly"-containing peptides. These results suggest that a cis hydroxyl group at the 3-position of the proline residue favors a pseudo,beta-turn-like nine-membered ring structure in hydroxyproline-containing peptides involving an intramolecular hydrogen bond between the hydroxyl and the i + 2 backbone amide.