3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-arabino-hex-1-enyl (5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-heptofuranosid)uronate | 302800-99-3

• 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: 3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-arabino-hex-1-enyl (5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-heptofuranosid)uronate
• 英文别名: [(2R,3S,4R)-1,3,4-tris(phenylmethoxy)hex-5-en-2-yl] 3-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propanoate
• CAS: 302800-99-3
• 化学式: C₃₈H₄₆O₉
• 分子量: 646.778
• InChiKey: RNMKMAFMIRZXQA-PDTFNXBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  47
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-arabino-hex-1-enyl (5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-heptofuranosid)uronate 在 Schrock catalyst 、 lead(II) chloride 四甲基乙二胺 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.75h， 生成 5-C-(2,6-anhydro-4,5,7-tri-O-benzyl-1,3-dideoxy-D-arabino-hept-2-enit-1-yl)-5-deoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylofuranose
  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：

  ((3aR,5R,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methanol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium hydroxide 、 swern reagent 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙酸乙酯 、 苯 为溶剂， -78.0~20.0 ℃ 、241.32 kPa 条件下， 生成 3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-arabino-hex-1-enyl (5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-heptofuranosid)uronate
  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.