ethyl 2,6-di-O-acetyl-1-thio-β-D-galactopyranoside | 503602-21-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,6-di-O-acetyl-1-thio-β-D-galactopyranoside
• CAS: 503602-21-9
• 化学式: C₁₂H₂₀O₇S
• 分子量: 308.353
• InChiKey: QYXRYTMDQCVKMF-IIRVCBMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.32
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  102.29
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl 2,6-di-O-acetyl-1-thio-β-D-galactopyranoside 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 、 sodium 、 四丁基碘化铵 、 二正丁基氧化锡 、 乙二胺 、 三乙胺 、 palladium dichloride 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 129.0h， 生成 octyl 2,4,6-tri-O-benzyl-3-O-diphenoxyphosphono-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and NMR characterization of the six regioisomeric monophosphates of octyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside

  摘要：

  All six regioisomeric monophosphates of octyl beta-D-galactopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside have been chemically synthesized and characterized by high-resolution H-1, C-13 and P-31 NMR spectroscopy. Phosphorylation causes characteristic downfield shifts of the nucleus at the substituted site in the H-1 and C-13 NMR signals and resulted in a unique P-31 signal for each compound. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00178-7
• 作为产物：
  描述：

  ethyl 2,6-di-O-acetyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 在 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 13.0h， 以95%的产率得到ethyl 2,6-di-O-acetyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and NMR characterization of the six regioisomeric monophosphates of octyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside

  摘要：

  All six regioisomeric monophosphates of octyl beta-D-galactopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside have been chemically synthesized and characterized by high-resolution H-1, C-13 and P-31 NMR spectroscopy. Phosphorylation causes characteristic downfield shifts of the nucleus at the substituted site in the H-1 and C-13 NMR signals and resulted in a unique P-31 signal for each compound. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00178-7

文献信息

• Acylation of carbohydrates over Al2O3: preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides
  作者：Pallavi Tiwari、Anup Kumar Misra

  DOI：10.1016/j.carres.2005.11.035

  日期：2006.2

  protocol does not require the addition of any base or activator. This methodology has been further extended to the selective acylation of carbohydrate diols and the one-pot preparation of acetylated glycosyl chlorides direct from free reducing sugars. The yields obtained in most of the cases are excellent.

  据报道，使用酰氯和固体支持剂Al2O3对碳水化合物衍生物进行选择性和全O酰化。该协议不需要添加任何碱或活化剂。该方法已经进一步扩展到碳水化合物二醇的选择性酰化和直接从游离还原糖直接制备一锅乙酰化糖基氯的方法。在大多数情况下所获得的产量是极好的。