[(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 | 439915-02-3

• 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)-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
• CAS: 439915-02-3
• 化学式: C₃₆H₄₂O₈S₃
• 分子量: 698.923
• InChiKey: BADKJXFLUFXYQN-MYCRHDQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  158
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  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 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 72.0h， 生成
  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：

  Phenyl 4-O-benzyl-1-thio-α-D-rhamnopyranoside 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 [(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
  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.