methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-gluco-octopyranosiduronic acid | 232603-09-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-gluco-octopyranosiduronic acid
• 英文别名: 3-[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]propanoic acid
• CAS: 232603-09-7
• 化学式: C₃₀H₃₄O₇
• 分子量: 506.596
• InChiKey: SNBBUURHRONPCF-TWZZTNFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-gluco-octopyranosiduronic 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 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
• 作为产物：
  描述：

  methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 Lindlar's catalyst lithium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 生成 methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-gluco-octopyranosiduronic acid
  参考文献：
  名称：

  通过烯烃复分解聚合制备1,6-连接的C-二糖

  摘要：

  3,4,6-三-O-苄基-1,2-二脱氧-d-阿拉伯糖基-己-1-烯醇（5a）与多种糖基羧酸6a-d的DCC介导的偶联反应得到酯7a -d的产量高。形成的酯的亚甲基化导致无环烯醇醚8a-d，并在盒子中在温暖的甲苯中暴露于Schrock钼催化剂1中，以良好的产率得到目标C-二糖二醇9a-d。将1，6-连接的基于葡萄糖的C-二糖聚糖9a转化为2-脱氧-β-葡萄糖衍生物10a以及相应的葡萄糖β-葡萄糖-C-二糖13。

  DOI：

  10.1016/s0040-4039(99)00815-1

文献信息

• Convergent preparation of 1,6-linked C-disaccharides via olefin metathesis
  作者：Maarten H.D. Postema、Daniel Calimente

  DOI：10.1016/s0040-4039(99)00815-1

  日期：1999.6

  The DCC mediated coupling reaction of 3,4,6-tri-O-benzyl-1,2-dideoxy-d-arabino-hex-1-enitol (5a) with a variety of sugar based carboxylic acids 6a-d gave esters 7a-d in good yield. Methylenation of the formed esters led to the acyclic enol ethers 8a-d and exposure to the Schrock molybdenum catalyst 1 in warm toluene, in the box, gave the target C-disaccharide glycals 9a-d in good yield. The 1,6-linked

  3,4,6-三-O-苄基-1,2-二脱氧-d-阿拉伯糖基-己-1-烯醇（5a）与多种糖基羧酸6a-d的DCC介导的偶联反应得到酯7a -d的产量高。形成的酯的亚甲基化导致无环烯醇醚8a-d，并在盒子中在温暖的甲苯中暴露于Schrock钼催化剂1中，以良好的产率得到目标C-二糖二醇9a-d。将1，6-连接的基于葡萄糖的C-二糖聚糖9a转化为2-脱氧-β-葡萄糖衍生物10a以及相应的葡萄糖β-葡萄糖-C-二糖13。
• 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.