3,4,6-tri-O-benzyl-1,2-dideoxy-D-arabino-hex-1-enyl (methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-gluco-octopyranosid)uronate | 232603-12-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-benzyl-1,2-dideoxy-D-arabino-hex-1-enyl (methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-gluco-octopyranosid)uronate
• 英文别名: [(2R,3S,4R)-1,3,4-tris(phenylmethoxy)hex-5-en-2-yl] 3-[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]propanoate
• CAS: 232603-12-2
• 化学式: C₅₇H₆₂O₁₀
• 分子量: 907.113
• InChiKey: KFSHBEXRLUHYHS-XCTMGFDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  67
• 可旋转键数：
  28
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-1,2-dideoxy-D-arabino-hex-1-enyl (methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-gluco-octopyranosid)uronate 在 <(F3C)2MeCO>2Mo=N(2,6-iPr2Ph)(=CHCMe2Ph) sodium hydroxide 、 硼烷四氢呋喃络合物 、 四甲基乙二胺 、 双氧水 、 四氯化钛 、 lead(II) chloride 、 锌 作用下， 以 甲苯 为溶剂， 生成
  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
• 作为产物：
  描述：

  methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 Lindlar's catalyst 4-二甲氨基吡啶 、 lithium hydroxide 、 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 为溶剂， 反应 12.0h， 生成 3,4,6-tri-O-benzyl-1,2-dideoxy-D-arabino-hex-1-enyl (methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-gluco-octopyranosid)uronate
  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

• 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.
• Synthesis and Partial Biological Evaluation of a Small Library of Differentially-Linked β-<i>C</i>-Disaccharides¹
  作者：Maarten H. D. Postema、Jared L. Piper、Lei Liu、Jie Shen、Marcus Faust、Peter Andreana

  DOI：10.1021/jo030039x

  日期：2003.6.1

  The synthesis of a small library of differentially-linked beta-C-disaccharides has been carried out through the use of a radical allylation-RCM strategy. Acids 6 were prepared by Keck allylation of a suitable carbohydrate-based radical precursor, followed by oxidative cleavage of the formed alkene. Dehydrative coupling of these acids with the known olefin alcohol 5 then gave the precursor esters 7 in excellent yield. Methylenation of the esters 7 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-disaccharides 10 in good overall yield. Five examples were then deprotected and screened for their efficacy as enzyme inhibitors of beta-glycosidase and against several solid-tumor cell lines for in vitro differential cytotoxicity.