(2S,3R,4S,5S,6S)-2-methoxy-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-5-[2-[(2R,3S,4R)-1,3,4-tris(phenylmethoxy)hex-5-en-2-yl]oxyprop-2-enyl]oxane | 557088-07-0

• 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: (2S,3R,4S,5S,6S)-2-methoxy-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-5-[2-[(2R,3S,4R)-1,3,4-tris(phenylmethoxy)hex-5-en-2-yl]oxyprop-2-enyl]oxane
• CAS: 557088-07-0
• 化学式: C₅₈H₆₄O₉
• 分子量: 905.141
• InChiKey: BBFBWABPJHMZEQ-XWWOETNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  67
• 可旋转键数：
  28
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  (2S,3R,4S,5S,6S)-2-methoxy-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-5-[2-[(2R,3S,4R)-1,3,4-tris(phenylmethoxy)hex-5-en-2-yl]oxyprop-2-enyl]oxane 在 tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride 硼烷 、 sodium hydroxide 、 双氧水 作用下， 以 甲苯 、 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以53%的产率得到(2S,3S,4R,5R,6R)-2-[[(2S,3S,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]methyl]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
  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：

  (3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene 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 19.0h， 生成 (2S,3R,4S,5S,6S)-2-methoxy-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-5-[2-[(2R,3S,4R)-1,3,4-tris(phenylmethoxy)hex-5-en-2-yl]oxyprop-2-enyl]oxane
  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

• 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.