(2R,3R,4S,5R,6S)-4-Allyl-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran | 557087-93-1

• 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: (2R,3R,4S,5R,6S)-4-Allyl-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran
• 英文别名: (2S,3R,4S,5R,6R)-2-methoxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-4-prop-2-enyloxane
• CAS: 557087-93-1
• 化学式: C₃₁H₃₆O₅
• 分子量: 488.624
• InChiKey: PGYYDZPYXRIFQO-SEZOVNKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  (2R,3R,4S,5R,6S)-4-Allyl-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran 在 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 、 叔丁醇 为溶剂， 反应 20.0h， 生成 (2S,3R,4S,5R,6R)-2-methoxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-4-[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
• 作为产物：
  描述：

  Methyl-2,4,6-tri-O-acetyl-3-O-phenoxythiocarbonyl-α-D-galactopyranosid 在 偶氮二异丁腈 、 sodium hydride 作用下， 以 甲醇 、 苯 为溶剂， 反应 15.5h， 生成 (2R,3R,4S,5R,6S)-4-Allyl-3,5-bis-benzyloxy-2-benzyloxymethyl-6-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

• 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.