(2R,3R,4S)-2,3-dihydroxy-5-trityloxy-4-pentanolide | 261967-42-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,3R,4S)-2,3-dihydroxy-5-trityloxy-4-pentanolide
• 英文别名: 5-O-triphenylmethyl-L-arabinono-γ-lactone；5-O-trityl-L-arabinono-γ-lactone；(3R,4R,5S)-3,4-dihydroxy-5-(trityloxymethyl)oxolan-2-one
• CAS: 261967-42-4
• 化学式: C₂₄H₂₂O₅
• 分子量: 390.436
• InChiKey: SEMNSEULNGXIGD-FDFHNCONSA-N

物化性质

• 沸点：
  546.8±19.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-2,3-dihydroxy-5-trityloxy-4-pentanolide 在 palladium on activated charcoal 2,6-二甲基吡啶 、 正丁基锂 、 camphor-10-sulfonic acid 、 氢气 、 三氟乙酸吡啶 、 四氯化锡 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 、 二甲基亚砜 为溶剂， 反应 79.75h， 生成 (4S,5S,6R)-2-(benzenesulfonyl)-4,5,6-tris[[tert-butyl(dimethyl)silyl]oxy]cyclohex-2-en-1-one
  参考文献：
  名称：

  The First Total Synthesis of Pyralomicin 1c.

  摘要：

  DOI：

  10.7164/antibiotics.53.88
• 作为产物：
  描述：

  L-arabinose 在 吡啶 、 4-二甲氨基吡啶 、 溴 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 17.0h， 生成 (2R,3R,4S)-2,3-dihydroxy-5-trityloxy-4-pentanolide
  参考文献：
  名称：

  使用苏式选择性羟醛缩合作为关键反应，从L-阿拉伯糖合成旋光性寡聚体型木脂素。

  摘要：

  由L-阿拉伯糖与胡椒醛制备的（3R，4S）-3-羟基-5-三苯甲氧基-4-戊醇的苏式选择性羟醛缩合反应用于木脂素的橄榄石型立体选择性合成（2R ，3R，4R）-4-苄基-4-羟基-3-羟基甲基-2-（3,4-亚甲基二氧苯基）四氢呋喃。

  DOI：

  10.1271/bbb.64.2320

文献信息

• The conversion of pentoses to 3,4-dihydroxyprolines
  作者：Carol M. Taylor、Chantelle E. Jones、Kristin Bopp

  DOI：10.1016/j.tet.2005.07.072

  日期：2005.10

  The synthesis of two naturally-occurring isomers of 3,4-dihydroxyproline is reported. L-2,3-cis-3,4-trans-3,4-Dihydroxyproli ne was synthesized from L-arabinose in 10 steps and 31 % overall yield. The same series of reactions was employed to convert L-xylose to L-2,3trans-3,4-trans-3,4-dihydroxyproline. Orthogonally protected versions of these amino acids were produced on gram scale, en route to the free amino acids, and these will serve as versatile intermediates in peptide synthesis. This synthetic strategy involved N alpha-Fmoc protection and protection of the C3 and C4 secondary alcohols as methoxyethoxymethyl (MEM) ethers. (c) 2005 Elsevier Ltd. All rights reserved.
• Toward a General Strategy for the Synthesis of 3,4-Dihydroxyprolines from Pentose Sugars
  作者：Carol M. Taylor、William D. Barker、Claudette A. Weir、Jae H. Park

  DOI：10.1021/jo025538x

  日期：2002.6.1

  A general strategy is proposed, wherein a pentose sugar gamma-lactone can be converted, via a series of nine reactions, to a 3,4-dihydroxyproline, suitably protected for use in peptide synthesis. Thus, D-ribonolactone (6) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-D-2,3-cis-3,4-cis-proline (7) in 18.9% overall yield. Likewise, L-arabinonolactone (11) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-L-2,3-cis-3,4-trans-proline (36) in 13.7% overall yield and L-lyxonolactone (12) to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-L-2,3-trans-3,4-cis-proline (37) in 11.2% overall yield. These building blocks have also been fully deprotected to give the free amino acids. We believe that this series of reactions ought to be applicable to the synthesis of any of the eight stereoisomers of 3,4-dihydroxyproline, by judicious selection of the pentose starting material.
• Synthesis of Optically Active Olivil Type of Lignan from <scp>L</scp>-Arabinose Using <i>threo</i>-Selective Aldol Condensation as a Key Reaction
  作者：Satoshi YAMAUCHI、Yoshiro KINOSHITA

  DOI：10.1271/bbb.64.2320

  日期：2000.1.1

  The threo-selective aldol condensation of (3R, 4S)-3-hydroxy-5-trityloxy-4-pentanolide, which was prepared from L-arabinose, with piperonal was applied to the stereoselective synthesis of the olivil type of lignan, (2R, 3R, 4R)-4-benzyl-4-hydroxy-3-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran.

  由L-阿拉伯糖与胡椒醛制备的（3R，4S）-3-羟基-5-三苯甲氧基-4-戊醇的苏式选择性羟醛缩合反应用于木脂素的橄榄石型立体选择性合成（2R ，3R，4R）-4-苄基-4-羟基-3-羟基甲基-2-（3,4-亚甲基二氧苯基）四氢呋喃。
• The First Total Synthesis of Pyralomicin 1c.
  作者：KUNIAKI TATSUTA、MASAAKI TAKAHASHI、NOBORU TANAKA

  DOI：10.7164/antibiotics.53.88

  日期：——