methyl 2-O-benzyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside | 365418-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2-O-benzyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside
• 英文别名: methyl 3-allyl-2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside；(2R,4aR,6S,7R,8S,8aS)-6-methoxy-2-phenyl-7-phenylmethoxy-8-prop-2-enyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 365418-34-4
• 化学式: C₂₄H₂₈O₅
• 分子量: 396.483
• InChiKey: HXGUWUSMALDAJG-FZPZUOBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-O-benzyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside 在 tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride 、 lead(II) chloride 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 四甲基乙二胺 、 四氯化钛 、 臭氧 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 25.0h， 生成
  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 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 在 吡啶 、 N-羟基丁二酰亚胺 、 偶氮二异丁腈 、 sodium hydride 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 19.0h， 生成 methyl 2-O-benzyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside
  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

• Designing an effective approach for obtaining methylenecarboxylate analogues of adenophostin A. Preliminary results
  作者：David Benito、M. Isabel Matheu、Alain Morère、Yolanda Díaz、Sergio Castillón

  DOI：10.1016/j.carres.2009.09.030

  日期：2009.12

  Preliminary results for the synthesis of two new adenophostin analogues incorporating 3''- and 4''-methylenecarboxylate surrogate groups are presented. The synthesis involves the preparation of 3''- and 4''-methylenecarboxylate glucose derivatives by a radical allylation-oxidative cleavage approach, their conversion into thioglycoside precursors, and stereoselective glycosylation of a suitable adenosine

  给出了合成两个新的包含3′-和4′-亚甲基羧酸酯替代基团的腺苷类似物的初步结果。合成涉及通过自由基烯丙基化-氧化裂解方法制备3′-和4′-亚甲基羧酸酯葡萄糖衍生物，将其转化为硫代糖苷前体，以及合适的腺苷衍生物的立体选择性糖基化。糖基化以优异的立体选择性进行，仅检测到α产物，并具有良好的产率。
• 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
• A Double Ring-Closing Metathesis Approach for the Synthesis ofβ-C-Trisaccharides
  作者：Maarten H. D. Postema、Jared L. Piper、Venu Komanduri、Lei Liu

  DOI：10.1002/anie.200353478

  日期：2004.5.24
• 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.