8-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-arabino-hex-1-enyl)-6,7,9-trideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-nona-8-enopyranose | 302800-94-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 8-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-arabino-hex-1-enyl)-6,7,9-trideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-nona-8-enopyranose
• 英文别名: (1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-8-[3-[(2R,3S,4R)-1,3,4-tris(phenylmethoxy)hex-5-en-2-yl]oxybut-3-enyl]-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 302800-94-8
• 化学式: C₄₂H₅₂O₉
• 分子量: 700.869
• InChiKey: QJODOXFZZCZYAH-CENHALDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  51
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  8-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-arabino-hex-1-enyl)-6,7,9-trideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-nona-8-enopyranose 在 Schrock catalyst 作用下， 以 甲苯 为溶剂， 以67%的产率得到6-C-(2,6-anhydro-4,5,7-tri-O-benzyl-1,3-dideoxy-D-arabino-hept-enit-1-yl)-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  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：

  6,7-Dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octapyranuronic acid 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 8-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-arabino-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

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.