1,6-anhydro-3,4-dideoxy-2-O-p-toluenesulfonyl-β-D-erythro-hex-3-enopyranose | 53716-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,6-anhydro-3,4-dideoxy-2-O-p-toluenesulfonyl-β-D-erythro-hex-3-enopyranose
• 英文别名: 1,6-Anhydro-3,4-dideoxy-2-O-tosyl-β-D-erythro-hex-3-enopyranose；1,6-Anhydro-3,4-dideoxy-2-O-p-toluolsulfonyl-β-D-erythro-hex-3-enopyranose；[(1S,4R,5R)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-yl] 4-methylbenzenesulfonate
• CAS: 53716-80-6
• 化学式: C₁₃H₁₄O₅S
• 分子量: 282.317
• InChiKey: HZQUMHXCPGRHTJ-CYZMBNFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-3,4-dideoxy-2-O-p-toluenesulfonyl-β-D-erythro-hex-3-enopyranose 在 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 25.0h， 生成 methyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3-dideoxy-4-thio-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Synthesis of S-linked glucosaminyl-4-thiohex-2-enopyranosides via allylic SN2′ substitution of a tosylhexenose

  摘要：

  Treatment of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-beta -D-glucopyranose with 1,6-anhydro-3,4-dideoxy-2-O-p-toluenesulfonyl-beta -D-erythro-hex-3-enopyranose gave 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 4)-1,6-anhydro-2,3-dideoxy-4-thio-beta -D-erythro-hex-2-enopyranose in 86% yield. Its 1,6-anhydride bond was cleaved with methanol to give a mixture of methyl glycosides (alpha/beta similar to 5:1), from which the alpha anomer was separated by crystallization and converted into its 6-acetate, 6-methanesulfonate, or deacetylated to obtain the corresponding free methyl thiodisaccharide. The structure of the new compounds was confirmed by H-1 and C-13 NMR spectra. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00175-6
• 作为产物：
  描述：

  1,6:3,4-二脱水-2-O-对甲苯磺酰基-beta-D-吡喃半乳糖 在 3-甲基-1,3-苯并噻唑-2-硒酮 、 trifluoroessigsaeure 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以75%的产率得到1,6-anhydro-3,4-dideoxy-2-O-p-toluenesulfonyl-β-D-erythro-hex-3-enopyranose
  参考文献：
  名称：

  Direkte Synthese von ungesättigten Kohlenhydraten und Cycliten aus Oxiranen

  摘要：

  DOI：

  10.1055/s-1980-29149

文献信息

• Synthesis of Unsaturated Sulfur-Linked (1→4)-Disaccharides by Substitution of Tosyloxy Group in 1,6-Anhydro-3,4-dideoxy-2-O-tosyl-β-D-erythro-hex-3-enopyranose with 1-Thiohexopyranoses
  作者：Petr Bartoš、Miloslav Černý、Iva Tišlerová、Tomáš Trnka

  DOI：10.1135/cccc20001737

  日期：——

  A novel method for the synthesis of unsaturated sulfur-linked (1→4)-disaccharides is described. The starting 1,6-anhydro-3,4-dideoxy-2-O-tosyl-β-D-erythro-hex-3-enopyranose (3) was reacted with potassium salt of acetylated 1-thiohexopyranoses of D-gluco-, D-galacto-, and L-galacto-configuration to give acetylated β-glycopyranosyl-(1→4)-1,6-anhydro-2,3-dideoxy-4-thio-β-D-erythro-hex-2-enopyranoses 8-10. Their acid methanolysis under mild conditions afforded the corresponding methyl glycosides 11-13. The structure of new compounds was confirmed by ¹H NMR and mass spectra data.

  描述了一种合成不饱和硫连接的（1→4）-二糖的新方法。起始物1,6-脱水-3,4-二脱氧-2-O-对甲苯磺酰-β-D-赤霉醇-3-烯吡喃糖（3）与D-葡萄糖、D-半乳糖和L-半乳糖构型的乙酰化1-硫代己糖吡喃糖的钾盐反应，得到了乙酰化的β-葡萄糖吡喃糖-(1→4)-1,6-脱水-2,3-二脱氧-4-硫-β-D-赤霉醇-2-烯吡喃糖（8-10）。它们在温和条件下进行酸甲醇解，得到相应的甲基糖苷（11-13）。新化合物的结构经过1H NMR和质谱数据确认。
• Direkte Synthese von ungesättigten Kohlenhydraten und Cycliten aus Oxiranen
  作者：Hans Paulsen、Fred R. Heiker、John Feldmann、Kurt Heyns

  DOI：10.1055/s-1980-29149

  日期：——
• Synthesis of S-linked glucosaminyl-4-thiohex-2-enopyranosides via allylic SN2′ substitution of a tosylhexenose
  作者：Jiřı́ Kroutil、Miloslav Černý、Tomáš Trnka、Miloš Buděšı́nský

  DOI：10.1016/s0008-6215(01)00175-6

  日期：2001.8

  Treatment of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-beta -D-glucopyranose with 1,6-anhydro-3,4-dideoxy-2-O-p-toluenesulfonyl-beta -D-erythro-hex-3-enopyranose gave 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 4)-1,6-anhydro-2,3-dideoxy-4-thio-beta -D-erythro-hex-2-enopyranose in 86% yield. Its 1,6-anhydride bond was cleaved with methanol to give a mixture of methyl glycosides (alpha/beta similar to 5:1), from which the alpha anomer was separated by crystallization and converted into its 6-acetate, 6-methanesulfonate, or deacetylated to obtain the corresponding free methyl thiodisaccharide. The structure of the new compounds was confirmed by H-1 and C-13 NMR spectra. (C) 2001 Elsevier Science Ltd. All rights reserved.