[(2S,3R,4S,5R,6R)-5-[(2S,3R,4S,5R,6R)-4-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyl-5-phenylmethoxy-3-phenylsulfanyloxan-2-yl]oxy-2-(4-methoxyphenoxy)-6-methyl-3-phenylsulfanyloxan-4-yl] methylsulfanylformate | 439915-06-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4S,5R,6R)-5-[(2S,3R,4S,5R,6R)-4-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyl-5-phenylmethoxy-3-phenylsulfanyloxan-2-yl]oxy-2-(4-methoxyphenoxy)-6-methyl-3-phenylsulfanyloxan-4-yl] methylsulfanylformate
• CAS: 439915-06-7
• 化学式: C₄₆H₅₄O₁₁S₃
• 分子量: 879.126
• InChiKey: IQHNXUCCRFEEIL-ZZMBKQRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  60
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  196
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  三氟甲烷磺酸甲酯 、 [(2S,3R,4S,5R,6R)-2-[[(3aS,4R,6R,7R,7aS)-6-methyl-4-phenylsulfanyl-2-sulfanylidene-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-6-methyl-5-phenylmethoxy-3-phenylsulfanyloxan-4-yl] acetate 、 [(2S,3R,4S,5R,6R)-5-[(2S,3R,4S,5R,6R)-4-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyl-5-phenylmethoxy-3-phenylsulfanyloxan-2-yl]oxy-2-(4-methoxyphenoxy)-6-methyl-3-phenylsulfanyloxan-4-yl] methylsulfanylformate 在 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以15%的产率得到Thiocarbonic acid O-[(2R,3R,4S,5R,6S)-3-((2S,3R,4S,5S,6R)-5-benzyloxy-4-hydroxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy)-6-(4-methoxy-phenoxy)-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-4-yl] ester S-methyl ester
  参考文献：
  名称：

  Efficient Synthesis of the Hexasaccharide Fragment of Landomycin A:  Using Phenyl 2,3-O-Thionocarbonyl-1-thioglycosides as 2-Deoxy-β-glycoside Precursors

  摘要：

  [GRAPHICS]The beta-p-methoxyphenol hexadeoxysaccharide fragment of landomycin A was synthesized in a total of 33 steps and 0.5% overall yield starting from D-mannose and D-Xylose, featuring the use of phenyl 2,3-O-thionocarbonyl-1-thioglycosides as 2-deoxy-beta-glycoside precursors.

  DOI：

  10.1021/ol0259286
• 作为产物：
  描述：

  [(2S,3R,4S,5R,6R)-2-[[(3aS,4R,6R,7R,7aS)-2,2,6-trimethyl-4-phenylsulfanyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-6-methyl-5-phenylmethoxy-3-phenylsulfanyloxan-4-yl] methylsulfanylformate 在 吡啶 、 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基吡啶 、 叔丁基二甲硅基三氟甲磺酸酯 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.33h， 生成 [(2S,3R,4S,5R,6R)-5-[(2S,3R,4S,5R,6R)-4-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyl-5-phenylmethoxy-3-phenylsulfanyloxan-2-yl]oxy-2-(4-methoxyphenoxy)-6-methyl-3-phenylsulfanyloxan-4-yl] methylsulfanylformate
  参考文献：
  名称：

  Efficient Synthesis of the Hexasaccharide Fragment of Landomycin A:  Using Phenyl 2,3-O-Thionocarbonyl-1-thioglycosides as 2-Deoxy-β-glycoside Precursors

  摘要：

  [GRAPHICS]The beta-p-methoxyphenol hexadeoxysaccharide fragment of landomycin A was synthesized in a total of 33 steps and 0.5% overall yield starting from D-mannose and D-Xylose, featuring the use of phenyl 2,3-O-thionocarbonyl-1-thioglycosides as 2-deoxy-beta-glycoside precursors.

  DOI：

  10.1021/ol0259286

文献信息

• Efficient Synthesis of the Hexasaccharide Fragment of Landomycin A:  Using Phenyl 2,3-<i>O</i>-Thionocarbonyl-1-thioglycosides as 2-Deoxy-β-glycoside Precursors
  作者：Biao Yu、Ping Wang

  DOI：10.1021/ol0259286

  日期：2002.5.1

  [GRAPHICS]The beta-p-methoxyphenol hexadeoxysaccharide fragment of landomycin A was synthesized in a total of 33 steps and 0.5% overall yield starting from D-mannose and D-Xylose, featuring the use of phenyl 2,3-O-thionocarbonyl-1-thioglycosides as 2-deoxy-beta-glycoside precursors.