methyl-[O⁴,O⁶-((S)-benzylidene)-β-D-gulopyranoside] | 1185860-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl-[O⁴,O⁶-((S)-benzylidene)-β-D-gulopyranoside]
• 英文别名: Methyl-[O⁴,O⁶-((S)-benzyliden)-β-D-gulopyranosid]；(2S,4aR,6R,7R,8S,8aR)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 1185860-21-2
• 化学式: C₁₄H₁₈O₆
• 分子量: 282.293
• InChiKey: VVSWDMJYIDBTMV-QTJJRWQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl-[O⁴,O⁶-((S)-benzylidene)-β-D-gulopyranoside] 在 叠氮化四丁基铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2-acetyl-3-azido-4,6-O-benzylidene-3-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of 3-azido-3-deoxy-β-d-galactopyranosides

  摘要：

  Three efficient routes to 3-azido-3-deoxy-beta-D-galactopyranosides were developed relying on a double inversion protocol at C3. Two of the routes were demonstrated to work with both O- and S-glycosides. In all three routes, the 2-O-acetyl-3-azido-4,6-O-benzylidene-3-deoxy-beta-D-galactopyranosides were obtained by an azide inversion of the key intermediates 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-D-gulopyranosides. The intermediate gulopyranosides were in turn obtained from 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-D-galactopyranosides, installed in one pot from the 4,6-O-benzylidene-beta-D-galactopyranosides, by inversion with nitrite or acetate. For O-glycosides, the gulopyranoside configuration could alternatively be obtained from the 4,6-O-benzylidene-beta-D-galactopyranoside by elimination to give the 2,3-dianhydro derivative followed by a highly stereoselective cis-dihydroxylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.05.005
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-2,3-dideoxy-β-D-threo-hex-2-enoside 在 三乙烯二胺 、 四氧化锇 、 甲基磺酰胺 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到methyl-[O⁴,O⁶-((S)-benzylidene)-β-D-gulopyranoside]
  参考文献：
  名称：

  Synthesis of 3-azido-3-deoxy-β-d-galactopyranosides

  摘要：

  Three efficient routes to 3-azido-3-deoxy-beta-D-galactopyranosides were developed relying on a double inversion protocol at C3. Two of the routes were demonstrated to work with both O- and S-glycosides. In all three routes, the 2-O-acetyl-3-azido-4,6-O-benzylidene-3-deoxy-beta-D-galactopyranosides were obtained by an azide inversion of the key intermediates 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-D-gulopyranosides. The intermediate gulopyranosides were in turn obtained from 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-D-galactopyranosides, installed in one pot from the 4,6-O-benzylidene-beta-D-galactopyranosides, by inversion with nitrite or acetate. For O-glycosides, the gulopyranoside configuration could alternatively be obtained from the 4,6-O-benzylidene-beta-D-galactopyranoside by elimination to give the 2,3-dianhydro derivative followed by a highly stereoselective cis-dihydroxylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.05.005

文献信息

• 493. Periodate oxidation. Part IV. The effect of conformation of cyclic glycols on the rate of periodate oxidation
  作者：John Honeyman、C. J. G. Shaw

  DOI：10.1039/jr9590002454

  日期：——
• Methyl β-D-Gulofuranoside and Certain Other Derivatives of D-Gulose
  作者：Hewitt G. Fletcher、Harry W. Diehl、Robert K. Ness

  DOI：10.1021/ja01640a049

  日期：1954.6
• Synthesis of 3-azido-3-deoxy-β-d-galactopyranosides
  作者：Christopher T. Öberg、Ann-Louise Noresson、Tamara Delaine、Amaia Larumbe、Johan Tejler、Henrik von Wachenfeldt、Ulf J. Nilsson

  DOI：10.1016/j.carres.2009.05.005

  日期：2009.7

  Three efficient routes to 3-azido-3-deoxy-beta-D-galactopyranosides were developed relying on a double inversion protocol at C3. Two of the routes were demonstrated to work with both O- and S-glycosides. In all three routes, the 2-O-acetyl-3-azido-4,6-O-benzylidene-3-deoxy-beta-D-galactopyranosides were obtained by an azide inversion of the key intermediates 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-D-gulopyranosides. The intermediate gulopyranosides were in turn obtained from 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-D-galactopyranosides, installed in one pot from the 4,6-O-benzylidene-beta-D-galactopyranosides, by inversion with nitrite or acetate. For O-glycosides, the gulopyranoside configuration could alternatively be obtained from the 4,6-O-benzylidene-beta-D-galactopyranoside by elimination to give the 2,3-dianhydro derivative followed by a highly stereoselective cis-dihydroxylation. (C) 2009 Elsevier Ltd. All rights reserved.