ethyl 2,4,6-tri-O-acetyl-3-O-allyl-1-thio-β-D-galactopyranoside | 503602-22-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,4,6-tri-O-acetyl-3-O-allyl-1-thio-β-D-galactopyranoside
• CAS: 503602-22-0
• 化学式: C₁₇H₂₆O₈S
• 分子量: 390.455
• InChiKey: XGOJMGNWPLYOLM-HMDCTGQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ethyl 2,4,6-tri-O-acetyl-3-O-allyl-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 、 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 、 叔丁醇 为溶剂， 反应 107.0h， 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 二正丁基氧化锡 、 溶剂黄146 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 35.0h， 生成 ethyl 2,4,6-tri-O-acetyl-3-O-allyl-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

• Total synthesis of the heptasaccharide repeating unit of the iron-binding exopolysaccharide secreted by Klebsiella oxytoca BAS-10
  作者：Goutam Guchhait、Anup Kumar Misra

  DOI：10.1016/j.tetasy.2009.07.009

  日期：2009.8

  The first total synthesis of a heptasaccharide found in the iron-binding exopolysaccharide produced by Klebsiella oxytoca BAS-10 has been achieved in excellent yield using a block synthetic strategy. A trisaccharide glycosyl donor was stereoselectively coupled with a tetrasaccharide glycosyl acceptor using the trichloroacetimidate activation procedure. The yields and stereo outcome were excellent in each step of glycosylation. A late stage oxidation protocol was adopted for the oxidation of the primary hydroxyl group to the carboxylic functionality while keeping a secondary hydroxyl group unaffected. (c) 2009 Elsevier Ltd. All rights reserved.