1,2,4,6-tetra-O-acetyl-α,β-D-glucopyranose | 95188-74-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,4,6-tetra-O-acetyl-α,β-D-glucopyranose
• 英文别名: 1,2,4,6-tetra-O-acetyl-glucopyranoside；1,2,4,6-Tetraacetyl-d-glucose；[(2R,3S,4S,5R)-3,5,6-triacetyloxy-4-hydroxyoxan-2-yl]methyl acetate
• CAS: 95188-74-2
• 化学式: C₁₄H₂₀O₁₀
• 分子量: 348.307
• InChiKey: VEXTUPCIMUQWAO-DYPLGBCKSA-N

物化性质

• 沸点：
  458.5±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2,4,6-tetra-O-acetyl-α,β-D-glucopyranose 在 4 A molecular sieve 、 三氟化硼乙醚 、 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1,2,4,6-tetra-O-acetyl-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of three diosgenyl saponins: dioscin, polyphyllin D, and balanitin 7

  摘要：

  Dioscin, polyphyllin D, and balanitin 7, which belong to a group of structurally similar diosgenyl saponins with promising bioactivities, were synthesized by stepwise glycosylation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00066-x
• 作为产物：
  描述：

  1,2,4,6-Tetra-O-acetyl-3-O-allyl-β-D-glucopyranose 在 sodium dithionite 、 碳酸氢钠 、 氯化铵 、 锌 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 0.75h， 生成 1,2,4,6-tetra-O-acetyl-α,β-D-glucopyranose
  参考文献：
  名称：

  A novel cleavage of allyl protection

  摘要：

  A novel, efficient, and mild cleavage of allyl protection is developed employing perfluoroalkylation and subsequent elimination. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00906-x

文献信息

• Modified kojibiosides analogues
  申请人：Alberta Research Council

  公开号：US05633233A1

  公开（公告）日：1997-05-27

  Disclosed are novel analogues of kojibiose and pharmaceutical compositions comprising such analogues.

  公开的是曲酸的新颖类似物以及包含这些类似物的药物组合物。
• Modified
  申请人：Alberta Research Council

  公开号：US05929037A1

  公开（公告）日：1999-07-27

  Disclosed is the trisaccharide .alpha.-D-Glcp-(1-2)-.alpha.-D-Glcp-(1-3)-.alpha.-D-Glcp and compounds related thereto as well as pharmaceutical compositions thereof.

  揭示了三糖α-D-Glcp-(1-2)-α-D-Glcp-(1-3)-α-D-Glcp及其相关化合物以及其药物组合物。
• Synthesis of two purple-membrane glycolipids and the glycolipid sulfate O-(β-d-glucopyranosyl 3-sulfate)-(1→6)-O-α-d-mannopyranosyl-(1→2)-O-α-d-glucopyranosyl-(1→1)-2, 3-di-O-phytanyl-sn-glycerol
  作者：Constant A.A. van Boeckel、Pieter Westerduin、Jacques H. van Boom

  DOI：10.1016/0008-6215(84)85200-3

  日期：1984.10

  The two purple-membrane glycolipids O-β-d-glucopyranosyl- and O-β-d-galactopyranosyl-(1→6)-O-α-d-mannopyranosyl-(1→2)-O-α-d-glucopyranosyl-(1→1)-2, 3-di-O-phytanyl-sn-glycerol were prepared by coupling O-(2,3,4-tri-O-acetyl-α-d-mannopyranosyl)-(1→2)-O-(3,4,6-tri-O-acetyl-α-d-glucopyranosyl)-(1→1)-2, 3-di-O-phytanyl-sn-glycerol (9) with 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide or 2,3,4,6-t

  两种紫色膜糖脂O-β-d-吡喃葡萄糖基-和O-β-d-吡喃吡喃糖基-（1→6）-O-α-d-甘露吡喃糖基-（1→2）-O-α-d-吡喃葡萄糖基-（1→1）-2，通过偶合O-（2,3,4-tri-O-乙酰基-α-d-甘露吡喃糖基）-（1→2）制备3-二-O-植烷酰基-sn-甘油）-O-（3,4,6-三-O-乙酰基-α-d-吡喃葡萄糖基）-（1→1）-2，3-二-O-植烷酰基-sn-甘油（9），含2,3分别将，4，6-四-O-乙酰基-α-d-吡喃葡萄糖基溴化物或2,3,4,6-四-O-乙酰基-α-d-甘氨酰吡喃糖基溴化物，然后脱乙酰化。糖脂硫酸盐O-（β-d-吡喃葡萄糖基硫酸酯）-（1→6）-O-α-d-甘露吡喃糖基-（1→2）-O-α-d-吡喃葡萄糖基-（1→1）-在Hg（存在）下将9与2,4,6-三-O-乙酰基-3-O-三氯乙氧基羰基-α-d-吡喃葡萄糖基溴化物偶合，制得2,3-二-O-植烷酰基-sn-甘油CN）2
• The Glc2Man2-fragment of the N-glycan precursor – a novel ligand for the glycan-binding protein malectin?
  作者：Lisa N. Müller、Claudia Muhle-Goll、Moritz B. Biskup

  DOI：10.1039/c004502k

  日期：——

  The Glcα(1→3)Glcα(1→3)Manα(1→2)Man tetrasaccharide (Glc2Man2-fragment), a substructure of the natural N-glycan precursor, was synthesized. The interaction of this fragment with the protein malectin, a carbohydrate binding protein localized in the endoplasmatic reticulum, was investigated by 1H15N HSQC experiments and isothermal calorimetry. The chemical shift perturbations of nuclei in the protein's backbone caused by the binding of the Glc2Man2-fragment to malectin suggest a binding mode like the known ligand nigerose.

  合成了天然N-糖苷前体的一个亚结构——Glcα(1→3)Glcα(1→3)Manα(1→2)Man四糖（Glc2Man2-片段）。通过1H15N HSQC实验和等温滴定量热法研究了该片段与定位于内质网的糖结合蛋白malectin的相互作用。Glc2Man2-片段与malectin结合引起的蛋白质主链中核的化学位移扰动暗示了其结合模式类似于已知的配体nigerose。
• A facile synthetic approach to a group of structurally typical diosgenyl saponins
  作者：Shaojiang Deng、Biao Yu、Yongzheng Hui

  DOI：10.1016/s0040-4039(98)01354-9

  日期：1998.9

  A facile approach was developed for synthesizing an important group of plant diosgenyl saponins, three members (dioscin, polyphyllin D, and balanitin 7) with promising bioactivities were prepared. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.