2'-O-(2-Acetamino-2-deoxy-β-D-glucopyranosyl)-glycerol | 23214-64-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-O-(2-Acetamino-2-deoxy-β-D-glucopyranosyl)-glycerol
• 英文别名: 2-O-(2-acetamido-2-deoxy-beta-d-glucopyranosyl)glycerol；N-[(2R,3R,4R,5S,6R)-2-(1,3-dihydroxypropan-2-yloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 23214-64-4
• 化学式: C₁₁H₂₁NO₈
• 分子量: 295.29
• InChiKey: MGEMEXOTADRXCR-ISUQUUIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (3aR)-2-甲基-5alpha-(乙酰氧基甲基)-6beta,7alpha-二乙酰氧基-3Aalpha,6,7,7Aalpha-四氢-5H-吡喃并[3,2-d]恶唑 在 palladium on activated charcoal 三氟甲磺酸 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 2'-O-(2-Acetamino-2-deoxy-β-D-glucopyranosyl)-glycerol
  参考文献：
  名称：

  Synthesis of Glycosyl Glycerols and Related Glycolipids

  摘要：

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.

  DOI：

  10.1080/07328309808007465

文献信息

• Determination, by gas liquid chromatography, of the anomeric configuration of a 2-acetamido-2-deoxy-d-glucopyranosyl residue linked to a secondary hydroxyl group of another sugar residue
  作者：S.Robert Sarfati

  DOI：10.1016/s0008-6215(00)80722-3

  日期：1981.8