(2S,3R,4R,5S,6R)-2-[[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]methyl]-6-(hydroxymethyl)oxane-3,4,5-triol | 557088-27-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5S,6R)-2-[[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]methyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 557088-27-4
• 化学式: C₁₄H₂₆O₁₀
• 分子量: 354.354
• InChiKey: QFBIAPYRKMVJMJ-IFFAEWNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2S,3R,4R,5S,6R)-2-[[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]methyl]-6-(hydroxymethyl)oxane-3,4,5-triol 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-methoxy-5-((2S,3S,4R,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-4-yl ester
  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：

  methyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside 在 tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride 、 palladium on activated charcoal 、 lead(II) chloride 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 偶氮二异丁腈 、 四甲基乙二胺 、 氢气 、 四氯化钛 、 sodium hydride 、 臭氧 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， -78.0~60.0 ℃ 、344.74 kPa 条件下， 反应 40.5h， 生成 (2S,3R,4R,5S,6R)-2-[[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]methyl]-6-(hydroxymethyl)oxane-3,4,5-triol
  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.