methyl 6-S-dodecyl-2,3-O-isopropylidene-6-thio-α-D-mannofuranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-S-dodecyl-2,3-O-isopropylidene-6-thio-α-D-mannofuranoside
• 英文别名: (1S)-1-[(3aS,4S,6R,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-dodecylsulfanylethanol
• 化学式: C₂₂H₄₂O₅S
• 分子量: 418.638
• InChiKey: FBTNBJABYURYKZ-MJCUULBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 2,3-O-isopropylidene-α-D-mannofuranoside 在 吡啶 、 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 sodium hydride 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 4.58h， 生成 methyl 6-S-dodecyl-2,3-O-isopropylidene-6-thio-α-D-mannofuranoside
  参考文献：
  名称：

  Regioselective synthesis of 6-S-alkyl and 6-S-glycosyl-6-thio-d-mannofuranose derivatives from 5,6-O-cyclic sulfate precursors

  摘要：

  C-6 opening of 5,6-cyclic sulfate derivatives of mannofuranose with a thiolate anion followed by acidic hydrolysis of the acyclic sulfate gave 6-S-alkyl derivatives in good yields (70-95%) and short reaction times (10-15 min). This methodology was applied to the synthesis of methyl 2,3-O-isopropylidene-6-S-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-6-thio-alpha-D-mannofuranoside (70%), 2,3-O-isopropylidene-6-S-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-6-thio-alpha-D-mannofuranose (87%) and 2,3-O-isopropylidene-6-S-(1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranos-6-yl)-6-thio-alpha-D-mannofuranose (87%). @ 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.05.016

文献信息

• Regioselective synthesis of 6-S-alkyl and 6-S-glycosyl-6-thio-d-mannofuranose derivatives from 5,6-O-cyclic sulfate precursors
  作者：Anne Wadouachi、Ludivine Lescureux、David Lesur、Daniel Beaupère

  DOI：10.1016/j.carres.2007.05.016

  日期：2007.8

  C-6 opening of 5,6-cyclic sulfate derivatives of mannofuranose with a thiolate anion followed by acidic hydrolysis of the acyclic sulfate gave 6-S-alkyl derivatives in good yields (70-95%) and short reaction times (10-15 min). This methodology was applied to the synthesis of methyl 2,3-O-isopropylidene-6-S-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-6-thio-alpha-D-mannofuranoside (70%), 2,3-O-isopropylidene-6-S-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-6-thio-alpha-D-mannofuranose (87%) and 2,3-O-isopropylidene-6-S-(1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranos-6-yl)-6-thio-alpha-D-mannofuranose (87%). @ 2007 Elsevier Ltd. All rights reserved.