isopropyl 1-thio-α-D-mannopyranoside | 936550-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 1-thio-α-D-mannopyranoside
• 英文别名: Isopropyl-a-D-thiomannopyranoside；(2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-propan-2-ylsulfanyloxane-3,4,5-triol
• CAS: 936550-10-6
• 化学式: C₉H₁₈O₅S
• 分子量: 238.305
• InChiKey: BPHPUYQFMNQIOC-XGQMLPDNSA-N

物化性质

• 沸点：
  438.4±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  isopropyl 1-thio-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 二正丁基氧化锡 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 6-azidohexyl 2,4,6-tri-O-acetyl-3-O-benzyl-α-D-mannopyranosyl-(1->3)-2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a fluorescence-labeled K30 antigen repeating unit using click chemistry

  摘要：

  An N-dansyl-labeled K30 antigen repeating unit, {4-[5-(N,N'-dimethylamino)naphthalene-1-sulfonamine]-1H-1,2,3-triazol-1-yl}hexyl beta-D-glucopyranosyluronate-(1 -> 3)-alpha-D-galactopyranosyl-alpha-D-mannopyranosyl-(1 -> 3)-beta-D-galactopyranoside, was synthesized using click chemistry, the copper(I)-catalyzed 1,3-dipolar cycloaddition reaction of an azide and an alkyne. The target compound could further facilitate the studies of interactions among K30 oligosaccharides and proteins. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.01.015
• 作为产物：
  描述：

  甘露糖 、 异丙硫醇 在 吡啶 、 乙酸酐 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 生成 isopropyl 1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of a fluorescence-labeled K30 antigen repeating unit using click chemistry

  摘要：

  An N-dansyl-labeled K30 antigen repeating unit, {4-[5-(N,N'-dimethylamino)naphthalene-1-sulfonamine]-1H-1,2,3-triazol-1-yl}hexyl beta-D-glucopyranosyluronate-(1 -> 3)-alpha-D-galactopyranosyl-alpha-D-mannopyranosyl-(1 -> 3)-beta-D-galactopyranoside, was synthesized using click chemistry, the copper(I)-catalyzed 1,3-dipolar cycloaddition reaction of an azide and an alkyne. The target compound could further facilitate the studies of interactions among K30 oligosaccharides and proteins. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.01.015

文献信息

• Direct 2,3-O-Isopropylidenation of α-D-Mannopyranosides and the Preparation of 3,6-Branched Mannose Trisaccharides
  作者：Rui Jiang、Guanghui Zong、Xiaomei Liang、Shuhui Jin、Jianjun Zhang、Daoquan Wang

  DOI：10.3390/molecules19056683

  日期：——

  A highly efficient, regioselective method for the direct 2,3-O-isopropylidenation of α-D-mannopyranosides is reported. Treatment of various α-D-mannopyranosides with 0.12 equiv of the TsOH·H2O and 2-methoxypropene at 70 °C gave 2,3-O-isopropylidene-α-D-mannopyranosides directly in 80%~90% yields. Based on this method, a 3,6-branched α-D-mannosyl trisaccharide was prepared in 50.4% total yield using p-nitrophenyl 2,3-O-isopropylidene-α-D-mannopyranoside as the starting material.

  报告了一种高效、具有区域选择性的 α-D-mannopyranosides 直接 2,3-O-异亚丙基化方法。在 70 °C 下，用 0.12 等量的 TsOH-H2O 和 2-甲氧基丙烯处理各种 α-D- 吡喃甘露糖苷，可直接得到 2,3-O-异亚丙基-α-D-吡喃甘露糖苷，收率在 80%~90% 之间。根据这种方法，以对硝基苯基 2,3-O-异亚丙基-α-D-吡喃甘露糖苷为起始原料，制备出了 3,6-支链α-D-甘露三糖，总产率为 50.4%。