(2S,4R,5S,6R)-3-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran | 365418-37-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4R,5S,6R)-3-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran
• CAS: 365418-37-7
• 化学式: C₃₁H₃₆O₅
• 分子量: 488.624
• InChiKey: WVPIKZFDHSKVEB-KQCKIEKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  36.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,4R,5S,6R)-3-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran 在 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 臭氧 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 19.0h， 生成 [(2R,3S,4R)-1,3,4-tris(phenylmethoxy)hex-5-en-2-yl] 2-[(2S,3S,4R,5S,6R)-2-methoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]acetate
  参考文献：
  名称：

  Synthesis and Partial Biological Evaluation of a Small Library of Differentially-Linked β-C-Disaccharides¹

  摘要：

  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.

  DOI：

  10.1021/jo030039x
• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 N-碘代丁二酰亚胺 、 偶氮二异丁腈 、 sodium hydride 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 27.5h， 生成 (2S,4R,5S,6R)-3-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran
  参考文献：
  名称：

  Synthesis and Partial Biological Evaluation of a Small Library of Differentially-Linked β-C-Disaccharides¹

  摘要：

  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.

  DOI：

  10.1021/jo030039x

文献信息

• A Unified Approach to Differentially Linked β-<i>C</i>-Disaccharides by Ring-Closing Metathesis
  作者：Lei Liu、Maarten H. D. Postema

  DOI：10.1021/ja010641+

  日期：2001.9.1