(2R,3S,4R)-1,3,4-tris(benzyloxy)hex-5-en-2-ol | 302800-64-2

• 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: (2R,3S,4R)-1,3,4-tris(benzyloxy)hex-5-en-2-ol
• 英文别名: 3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enitol；(2R,3S,4R)-1,3,4-tris(phenylmethoxy)hex-5-en-2-ol
• CAS: 302800-64-2
• 化学式: C₂₇H₃₀O₄
• 分子量: 418.533
• InChiKey: UMEFSOQWEOCALN-PFBJBMPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-1,3,4-tris(benzyloxy)hex-5-en-2-ol 在 lead(II) chloride 4-二甲氨基吡啶 、 四甲基乙二胺 、 四氯化钛 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 methyl 8-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enyl)-6,7,9-trideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-nona-8-enopyranose
  参考文献：
  名称：

  An Olefin Metathesis Route for the Preparation of (1→6)-Linked C-Disaccharide Glycals. A Convergent and Flexible Approach to C-Saccharide Synthesis

  摘要：

  A convergent route to a variety of C-1-disaccharide glycals based on the olefin metathesis reaction of enol ethers and alkenes is described. The DCC-mediated coupling reaction of a variety of pentose enitols (la-c) with a number of C-5- and C-6-monosaccharide carboxylic acids (2a-e) gave the corresponding esters 3a-1 in good yield. Methylenation of these compounds was followed by ring-closing metathesis, mediated by the Schrock molybdenum catalyst 8 in warm toluene, to provide the target C-disaccharide glycals 5a-1. The formed enol ether double bond in 5a was then transformed, via standard manipulations, into a variety of C-disaccharide derivatives 21-25.

  DOI：

  10.1021/jo0005159
• 作为产物：
  描述：

  D-lyxose 在 正丁基锂 、 硫酸 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.58h， 生成 (2R,3S,4R)-1,3,4-tris(benzyloxy)hex-5-en-2-ol
  参考文献：
  名称：

  An Olefin Metathesis Route for the Preparation of (1→6)-Linked C-Disaccharide Glycals. A Convergent and Flexible Approach to C-Saccharide Synthesis

  摘要：

  A convergent route to a variety of C-1-disaccharide glycals based on the olefin metathesis reaction of enol ethers and alkenes is described. The DCC-mediated coupling reaction of a variety of pentose enitols (la-c) with a number of C-5- and C-6-monosaccharide carboxylic acids (2a-e) gave the corresponding esters 3a-1 in good yield. Methylenation of these compounds was followed by ring-closing metathesis, mediated by the Schrock molybdenum catalyst 8 in warm toluene, to provide the target C-disaccharide glycals 5a-1. The formed enol ether double bond in 5a was then transformed, via standard manipulations, into a variety of C-disaccharide derivatives 21-25.

  DOI：

  10.1021/jo0005159

文献信息

• An In-Depth Study on Ring-Closing Metathesis of Carbohydrate-Derived α-Alkoxyacrylates:  Efficient Syntheses of DAH, KDO, and 2-Deoxy-β-KDO
  作者：Koen F. W. Hekking、Marcel A. H. Moelands、Floris L. van Delft、Floris P. J. T. Rutjes

  DOI：10.1021/jo060913x

  日期：2006.8.1

  Novel, efficient synthetic pathways to DAH, KDO, and 2-deoxy-β-KDO are described. Ring-closing metathesis (RCM) of highly functionalized α-alkoxyacrylate fragments resulted in a series of synthetically versatile oxygen heterocyclic intermediates. Further functionalization of the resulting enol ether double bond and subsequent deprotection provided the natural products in high overall yields, starting

  描述了通往DAH，KDO和2-deoxy-β-KDO的新颖，有效的合成途径。高度官能化的α-烷氧基丙烯酸酯片段的闭环复分解（RCM）导致了一系列合成上通用的氧杂环中间体。从可商购的被保护的糖开始，所得烯醇醚双键的进一步官能化和随后的脱保护以高的总收率提供了天然产物。
• RCM-Based Synthesis of a Variety of β-<i>C</i>-Glycosides and Their in Vitro Anti-Solid Tumor Activity
  作者：Maarten H. D. Postema、Jared L. Piper、Russell L. Betts、Frederick A. Valeriote、Halina Pietraszkewicz

  DOI：10.1021/jo040254t

  日期：2005.2.1

  The synthesis of a number of biologically relevant C-glycosides has been carried out through the use of an esterification-ring-closing metathesis (RCM) strategy. The required acid precursors were readily prepared via a number of standard chemical transformations followed by dehydrative coupling of these acids with several olefin alcohols 1 to yield the precursor esters 3 in excellent yield. Methylenation of the esters 3 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-glycosides 6 in good overall yield. Several examples were converted to the corresponding C-glycoglycerolipids 17 and subsequently screened against solid-tumor cell lines for in vitro differential cytotoxicity.
• Synthesis of Some Biologically Relevant β-<i>C</i>-Glycoconjugates
  作者：Maarten H. D. Postema、Jared L. Piper

  DOI：10.1021/ol034363q

  日期：2003.5.1

  [GRAPHICS]An esterification-RCM approach to a variety of biologically relevant beta-C-glycoconjugates is reported herein. A range of carboxylic acids were coupled with several different olefin alcohols 1 to provide esters 3. The esters were then converted to the final ring-closed product 6 in three steps in 49-60% overall yield. The formed compounds are biologically relevant and serve as stable carbohydrate mimics of the corresponding O-glycosides.
• A Double Ring-Closing Metathesis Approach for the Synthesis ofβ-C-Trisaccharides
  作者：Maarten H. D. Postema、Jared L. Piper、Venu Komanduri、Lei Liu

  DOI：10.1002/anie.200353478

  日期：2004.5.24
• Synthesis and anti-tumor activity of β-C-glycoside analogs of the immunostimulant KRN7000
  作者：Mani Raj Chaulagain、Maarten H.D. Postema、Fred Valeriote、Halina Pietraszkewicz

  DOI：10.1016/j.tetlet.2004.07.163

  日期：2004.10

  A ring-closing metathesis approach was employed for the synthesis of a beta-C-glycoside analog of the immunostimulant KRN7000. The protected Gglycosyl amino acid derivative 18 was converted to amino-olefin 20, and osmylation served to install the diol unit as a mixture of separable syn and anti isomers. Deprotection to the hydroxy-amine 21 was followed by N-acylation and debenzylation to deliver the target compound 5. (C) 2004 Elsevier Ltd. All rights reserved.