O¹,O²,O³,O⁴-Tetraacetyl-O⁶-(tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranose | 41545-70-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O¹,O²,O³,O⁴-Tetraacetyl-O⁶-(tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranose
• 英文别名: Gal2Ac3Ac4Ac6Ac(b1-6)b-Glc1Ac2Ac3Ac4Ac；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5R,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 41545-70-4
• 化学式: C₂₈H₃₈O₁₉
• 分子量: 678.598
• InChiKey: GNTLGGDVHFXGLI-SJSKHYGQSA-N

物化性质

• 熔点：
  166 °C(Solv: ethanol (64-17-5))
• 沸点：
  661.4±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  47
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  238
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  O¹,O²,O³,O⁴-Tetraacetyl-O⁶-(tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranose 在 乙酸肼 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 2,3,4-tri-O-acetyl-6-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-1-O-(N-allyl)carbamoyl-α-D-glucopyranose
  参考文献：
  名称：

  Oligosaccharide Synthesis via Electrophile-Induced Activation of Glycosyl-N-Allylcarbamates

  摘要：

  Glycosyl-N-allyl carbamates, obtained by reaction of anomerically unprotected saccharides with allyl isocyanate, can be activated by an electrophile-induced cyclisation and reacted with glycosyl accepters to form the corresponding oligosaccharides. By this method the mucin core 2 trisaccharide(2) has successfully been synthesized. Due to the mild glycosylation conditions even 1-O-acetyl protected glycosyl accepters can be used. This was demonstrated in the synthesis of a 1,6-linked glucosyl trisaccharide whereby a reptitious glycosylation strategy could be applied.

  DOI：

  10.1080/07328309808002350
• 作为产物：
  描述：

  2,3,4,6-O-四乙酰基-D-半乳糖 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.75h， 生成 O¹,O²,O³,O⁴-Tetraacetyl-O⁶-(tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranose
  参考文献：
  名称：

  Oligosaccharide Synthesis via Electrophile-Induced Activation of Glycosyl-N-Allylcarbamates

  摘要：

  Glycosyl-N-allyl carbamates, obtained by reaction of anomerically unprotected saccharides with allyl isocyanate, can be activated by an electrophile-induced cyclisation and reacted with glycosyl accepters to form the corresponding oligosaccharides. By this method the mucin core 2 trisaccharide(2) has successfully been synthesized. Due to the mild glycosylation conditions even 1-O-acetyl protected glycosyl accepters can be used. This was demonstrated in the synthesis of a 1,6-linked glucosyl trisaccharide whereby a reptitious glycosylation strategy could be applied.

  DOI：

  10.1080/07328309808002350

文献信息

• Per-O-acetylation of sugars catalysed by montmorillonite K-10
  作者：Pallooru Muni Bhaskar、Duraikkannu Loganathan

  DOI：10.1016/s0040-4039(98)00178-6

  日期：1998.4

  The inexpensive solid acid montmorillonite K-10, is shown to be an efficient catalyst for the per-O-acetylation of several mono-, di- and trisaccharides. The pyranose forms accounted for 75-100% of the acetylated products. (C) 1998 Elsevier Science Ltd. Ail rights reserved.
• Helferich; Sparmberg, Chemische Berichte, 1933, vol. 66, p. 806
  作者：Helferich、Sparmberg

  DOI：——

  日期：——
• Helferich; Rauch, Chemische Berichte, 1926, vol. 59, p. 2655
  作者：Helferich、Rauch

  DOI：——

  日期：——
• Masamune; Kamiyama, Tohoku Journal of Experimental Medicine, 1957, vol. 66, p. 43,48
  作者：Masamune、Kamiyama

  DOI：——

  日期：——
• In Situ Preparation of β-<scp>d</scp>-1-<i>O</i>-Hydroxylamino Carbohydrate Polymers Mediated by Galactose Oxidase
  作者：Peter R. Andreana、Wenhua Xie、Huai N. Cheng、Lei Qiao、Dennis J. Murphy、Qu-Ming Gu、Peng G. Wang

  DOI：10.1021/ol0258379

  日期：2002.5.1

  [GRAPHICS]Galactose oxidase produced a C-6 aldehyde in various terminal-containing galactose hydroxylamines for the simultaneous in situ generation of an A-B type condensation for the construction of unique oxime polymers. Molecular weights of the corresponding polymers were determined to be in the range of 4200-8900 g/mol, respectively. This indicates that approximately 20-25 sugar units were incorporated in these unique polymers.