Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylsulfanyl-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-tetrahydro-pyran-4-yl ester | 627509-63-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylsulfanyl-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3R,4S,5R,6R)-3,4-diacetyloxy-5-acetylsulfanyl-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 627509-63-1
• 化学式: C₂₆H₃₈O₁₄S
• 分子量: 606.645
• InChiKey: XMVCRQXZTLIZSI-SPIMTWJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  186
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylsulfanyl-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-tetrahydro-pyran-4-yl ester 在 Ra-Ni 作用下， 以77%的产率得到1,2:3,4-di-O-isopropylidene-6-O-(3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-hexopyranosyl)-α-D-galactopyranose
  参考文献：
  名称：

  Recent advances in the synthesis of 2-deoxy-glycosides

  摘要：

  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.

  DOI：

  10.1016/j.carres.2009.07.013
• 作为产物：
  描述：

  1,3,4,6-四-氧-乙酰-Β-D-吡啶甘露糖 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylsulfanyl-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Glycosylation with 2′-thio-S-acetyl participation

  摘要：

  The reaction of 1,2,3,4,6-penta-O,S,O,O,O-acetyl-2-thio-beta-D-glucopyranose with glycosyl acceptors in the presence of trimethylsilyl triflate leads to the beta-disaccharides exclusively, owing to especially avid anchimeric assistance by the 2-thio-S-acetyl group. Optional reductive removal of -SAc with Ra-Ni gives the corresponding 2'-deoxy-beta-disaccharides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.063