(2S,3R,4R,5S)-3,4-Dihydroxy-2,5-bis-(4-methoxy-benzyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | 419564-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R,4R,5S)-3,4-Dihydroxy-2,5-bis-(4-methoxy-benzyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,3R,4R,5S)-3,4-dihydroxy-2,5-bis[(4-methoxyphenyl)methoxymethyl]pyrrolidine-1-carboxylate
• CAS: 419564-84-4
• 化学式: C₂₇H₃₇NO₈
• 分子量: 503.593
• InChiKey: PJFPLDCBLHZYQQ-CXSMSNRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5S)-3,4-Dihydroxy-2,5-bis-(4-methoxy-benzyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 在 重铬酸吡啶 、 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 、 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 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.75h， 生成 (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2,5-bis-{[((S)-1-methoxycarbonyl-3-methyl-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 、 三氯化铝 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (2S,3R,4R,5S)-3,4-Dihydroxy-2,5-bis-(4-methoxy-benzyloxymethyl)-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.