methyl 8-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enyl)-6,7,9-trideoxy-α-D-gluco-nona-8-enopyranoside | 302800-86-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 8-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enyl)-6,7,9-trideoxy-α-D-gluco-nona-8-enopyranoside
• 英文别名: (2S,3R,4S,5R,6R)-2-methoxy-3,4,5-tris(phenylmethoxy)-6-[3-[(2R,3R,4R)-1,3,4-tris(phenylmethoxy)hex-5-en-2-yl]oxybut-3-enyl]oxane
• CAS: 302800-86-8
• 化学式: C₅₈H₆₄O₉
• 分子量: 905.141
• InChiKey: GVTLITJKJHFNOA-YWMWJPHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  67
• 可旋转键数：
  28
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 8-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enyl)-6,7,9-trideoxy-α-D-gluco-nona-8-enopyranoside 在 Schrock catalyst 作用下， 以 甲苯 为溶剂， 以71%的产率得到methyl 6-C-(2,6-anhydro-4,5,7-tri-O-benzyl-1,3-dideoxy-D-lyxo-hept-2-enit-1-yl)-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopytanoside
  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 lead(II) chloride 4-二甲氨基吡啶 、 正丁基锂 、 四甲基乙二胺 、 硫酸 、 四氯化钛 、 sodium hydride 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.33h， 生成 methyl 8-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enyl)-6,7,9-trideoxy-α-D-gluco-nona-8-enopyranoside
  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 Olefin Metathesis Route for the Preparation of (1→6)-Linked <i>C</i>-Disaccharide Glycals. A Convergent and Flexible Approach to <i>C</i>-Saccharide Synthesis
  作者：Maarten H. D. Postema、Daniel Calimente、Lei Liu、Tonja L. Behrmann

  DOI：10.1021/jo0005159

  日期：2000.9.1

  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.