3-O-methyl-D-mannose | 27552-10-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-methyl-D-mannose
• 英文别名: O³-methyl-D-mannose；3-O-Methyl-D-mannopyranose；(3S,4S,5R,6R)-6-(hydroxymethyl)-4-methoxyoxane-2,3,5-triol
• CAS: 27552-10-9
• 化学式: C₇H₁₄O₆
• 分子量: 194.185
• InChiKey: SCBBSJMAPKXHAH-BWSJPXOBSA-N

物化性质

• 沸点：
  406.3±45.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

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-D-mannose 生成 (5R,6R,7aS)-5-(hydroxymethyl)-7-methoxy-2-phenyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-6-ol
  参考文献：
  名称：

  PATRONI, JOSEPH J.;STICK, ROBERT V.;TILBROOK, D. MATTHEW G.;SKELTON, BRIA+, AUSTRAL. J. CHEM., 42,(1989) N2, C. 2127-2141

  摘要：

  DOI：
• 作为产物：
  描述：

  3-O-methyl-D-glucopyranose 在 水 、 二正丁基氧化锡 作用下， 生成 3-O-methyl-D-mannose
  参考文献：
  名称：

  Epimerization of Carbohydrates via Stannylene Acetals. A Practical Synthesis of D-Talose

  摘要：

  When treated with Bu2SnO in a suitable solvent, reducing sugars preferentially form 1,2-O-stannylene acetals and, on prolonged treatment with a slight excess of the reagent at reflux temperature, they undergo epimerization. This allows simple preparation of rare monosaccharides from readily available, unprotected starting materials. The process is equilibrium driven, and the equilibrium is shifted largely in favor of structures having an axial hydroxyl group at position 2.

  DOI：

  10.1080/07328309808002337

文献信息

• PATRONI, JOSEPH J.;STICK, ROBERT V.;TILBROOK, D. MATTHEW G.;SKELTON, BRIA+, AUSTRAL. J. CHEM., 42,(1989) N2, C. 2127-2141
  作者：PATRONI, JOSEPH J.、STICK, ROBERT V.、TILBROOK, D. MATTHEW G.、SKELTON, BRIA+

  DOI：——

  日期：——
• 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.
• Epimerization of Carbohydrates via Stannylene Acetals. A Practical Synthesis of D-Talose
  作者：György Hodosi、Pavol Kovác

  DOI：10.1080/07328309808002337

  日期：1998.5.1

  When treated with Bu2SnO in a suitable solvent, reducing sugars preferentially form 1,2-O-stannylene acetals and, on prolonged treatment with a slight excess of the reagent at reflux temperature, they undergo epimerization. This allows simple preparation of rare monosaccharides from readily available, unprotected starting materials. The process is equilibrium driven, and the equilibrium is shifted largely in favor of structures having an axial hydroxyl group at position 2.