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 | 439915-04-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: [(2S,3R,4S,5R,6R)-5-[(2S,3R,4S,5S,6R)-4-hydroxy-6-methyl-5-phenylmethoxy-3-phenylsulfanyloxan-2-yl]oxy-2-(4-methoxyphenoxy)-6-methyl-3-phenylsulfanyloxan-4-yl] methylsulfanylformate
• CAS: 439915-04-5
• 化学式: C₄₀H₄₄O₉S₃
• 分子量: 764.982
• InChiKey: SVTGPVSICVXXOT-UBEKCEMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  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 在 叔丁基二甲硅基三氟甲磺酸酯 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.33h， 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
• 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 、 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 92.0h， 生成 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

文献信息

• Recent advances in the synthesis of 2-deoxy-glycosides
  作者：Dianjie Hou、Todd L. Lowary

  DOI：10.1016/j.carres.2009.07.013

  日期：2009.10

  Glycosides of 2-deoxy-sugars, monosaccharides in which the hydroxyl group at C-2 is replaced with a hydrogen atom, occur widely in natural products and therefore have been the subject of intense synthetic activity. The report summarizes recent advances in this area, with a particular focus on work published since an earlier review on the topic, in 2000 (Marzabadi, C. H.: Franck, R. W. Tetrahedron 2000, 56, 8385-8417). (C) 2009 Elsevier Ltd. All rights reserved.
• 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.