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 | 374906-72-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-[[(2R,3S,6S)-2-(hydroxymethyl)-6-methoxy-3,6-dihydro-2H-pyran-3-yl]sulfanyl]oxan-2-yl]methyl acetate
• CAS: 374906-72-6
• 化学式: C₂₁H₃₁NO₁₁S
• 分子量: 505.543
• InChiKey: LHPDSOSFPJXPGX-HXAVOKFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  181
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  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 在 吡啶 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 43.0h， 生成 methyl 2-acetamido-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：

  2-乙酰氨基-2-脱氧-1-硫代-beta-D-吡喃葡萄糖 3,4,6-三乙酸酯 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