methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-2-O-trifluoromethanesulfonyl-L-idofuranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-2-O-trifluoromethanesulfonyl-L-idofuranoside
• 英文别名: [(3R,4S,5R)-2-methoxy-5-[(1S)-2-nitro-1-phenylmethoxyethyl]-4-phenylmethoxyoxolan-3-yl] trifluoromethanesulfonate
• 化学式: C₂₂H₂₄F₃NO₉S
• 分子量: 535.495
• InChiKey: AUXHDMWJBHLDOT-JFROBXPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-2-O-trifluoromethanesulfonyl-L-idofuranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以36%的产率得到(3R,5R,6S,7R)-6,7-dibenzyloxy-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. Part 2: Synthesis of (1S,2R,3S,4S,5R)-3,4,5-trihydroxy-2-aminocyclopentanecarboxylic acid

  摘要：

  A recent new strategy for the transformation of nitrohexofuranoses into cyclopentylamines, based on intramolecular cyclization followed by controlled opening of the resulting 2-oxabicyclo[2.2.1]heptane derivatives, allowed the first total synthesis of (1S,2R,3S,4S,5R)-2,3,4-trihydroxy-5-aminocyclopentanecarboxylic acid from L-idose. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.034
• 作为产物：
  描述：

  3,5-di-O-benzyl-6-deoxy-6-nitro-1,2-O-isopropylidene-β-L-idofuranose 在 吡啶 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 14.5h， 生成 methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-2-O-trifluoromethanesulfonyl-L-idofuranoside
  参考文献：
  名称：

  Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. Part 2: Synthesis of (1S,2R,3S,4S,5R)-3,4,5-trihydroxy-2-aminocyclopentanecarboxylic acid

  摘要：

  A recent new strategy for the transformation of nitrohexofuranoses into cyclopentylamines, based on intramolecular cyclization followed by controlled opening of the resulting 2-oxabicyclo[2.2.1]heptane derivatives, allowed the first total synthesis of (1S,2R,3S,4S,5R)-2,3,4-trihydroxy-5-aminocyclopentanecarboxylic acid from L-idose. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.034

文献信息

• New Morphiceptin Peptidomimetic Incorporating (1S,2R,3S,4S,5R)-2-Amino-3,4,5-trihydroxycyclopen-tane-1-carboxylic acid: Synthesis and Structural Study
  作者：Raquel Soengas、Marcos Lorca、Begoña Pampín、Víctor M. Sánchez-Pedregal、Ramón J. Estévez、Juan C. Estévez

  DOI：10.3390/molecules25112574

  日期：——

  We present the synthesis and structural study of a new peptidomimetic of morphiceptin, which can formally be considered as the result of the replacement of the central proline residue of this natural analgesic drug with a subunit of (1S,2R,3S,4S,5R)-2-amino-3,4,5-trihydroxycyclopentane-1-carboxylic acid, previously obtained from L-idose. An optimized synthesis of this trihydroxylated cispentacin derivative

  我们提出了一种新的吗啡肽模拟肽的合成和结构研究，它可以正式被认为是用 (1S,2R,3S,4S,5R) 亚基取代这种天然镇痛药的中心脯氨酸残基的结果-2-氨基-3,4,5-三羟基环戊烷-1-羧酸，之前从 L-idose 中获得。还报道了这种三羟基化顺喷他星衍生物的优化合成。对目标受体的分子对接计算支持非天然 β-氨基酸的羟基取代基的有利作用并入肽模拟物。