3-O-methyl-β-D-mannopyranose | 55058-38-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-methyl-β-D-mannopyranose
• 英文别名: β-D-Mannose-3-O-methylaether；O³-methyl-D-mannose；O³-methyl-β-D-mannopyranose；(2R,3S,4S,5R,6R)-6-(hydroxymethyl)-4-methoxyoxane-2,3,5-triol
• CAS: 55058-38-3
• 化学式: C₇H₁₄O₆
• 分子量: 194.185
• InChiKey: SCBBSJMAPKXHAH-ULQPCXBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-O-methyl-β-D-mannopyranose 、 苯甲酰氯 在 碳酸氢钠 作用下， 以 吡啶 为溶剂， 反应 24.0h， 生成 1,2,4,6-tetra-O-benzoyl-3-O-methyl-β-D-mannopyranose
  参考文献：
  名称：

  Isolation and identification of poly-α-(1→4)-linked 3-O-methyl-d-mannopyranose from a hot-water extract of Mycobacterium vaccae

  摘要：

  A polysaccharide around 3.6 kDa has been identified as the major carbohydrate moiety of a antineoplastic protein-polysaccharide complex (PS4A) obtained by boiling intact cells of Mycobacterium vaccae in water. H-1 and C-13 NMR spectra of this polysaccharide suggested it was a highly homogeneous polymer composed substantially of one monomer, probably an alpha-linked O-methylated mannose. Comparison of the COSY spectra of the original and acetylated polymer indicated that the glycosidic linkage and the methyl ether were interchangeable, at O-3 and O-4. Further study demonstrated that the benzyolated hydrolysate of the polymer was 1,2,4,6-tetra-O-benzoyl-3-O-methyl-beta-mannopyranose. The hydrolysate was 3-O-methyl-alpha,beta-mannopyranose and the polymer was therefore poly-alpha-(1 --> 4)-linked 3-O-methyl-D-mannopyranose. This conclusion was further confirmed with an authentic sample of the monomer, which had spectral data identical to those of the hydrolyzate and co-eluted from an ion-exchange HPLC with the major sugar in the hydrolysate. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00248-7

文献信息

• Isolation and identification of poly-α-(1→4)-linked 3-O-methyl-d-mannopyranose from a hot-water extract of Mycobacterium vaccae
  作者：Xin-Xin Tian、Afeng Li、Isabelle V Farrugia、Xuesheng Mo、David Crich、Michael J Groves

  DOI：10.1016/s0008-6215(99)00248-7

  日期：2000.1

  A polysaccharide around 3.6 kDa has been identified as the major carbohydrate moiety of a antineoplastic protein-polysaccharide complex (PS4A) obtained by boiling intact cells of Mycobacterium vaccae in water. H-1 and C-13 NMR spectra of this polysaccharide suggested it was a highly homogeneous polymer composed substantially of one monomer, probably an alpha-linked O-methylated mannose. Comparison of the COSY spectra of the original and acetylated polymer indicated that the glycosidic linkage and the methyl ether were interchangeable, at O-3 and O-4. Further study demonstrated that the benzyolated hydrolysate of the polymer was 1,2,4,6-tetra-O-benzoyl-3-O-methyl-beta-mannopyranose. The hydrolysate was 3-O-methyl-alpha,beta-mannopyranose and the polymer was therefore poly-alpha-(1 --> 4)-linked 3-O-methyl-D-mannopyranose. This conclusion was further confirmed with an authentic sample of the monomer, which had spectral data identical to those of the hydrolyzate and co-eluted from an ion-exchange HPLC with the major sugar in the hydrolysate. (C) 2000 Elsevier Science Ltd. All rights reserved.