O⁴-sulfo-L-6-deoxy-galactose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O⁴-sulfo-L-6-deoxy-galactose
• 英文别名: O⁴-sulfo-ξ-L-6-deoxy-galactopyranose；4-Mono-o-sulfo-l-fucopyranose；[(2S,3S,4S,5S)-4,5,6-trihydroxy-2-methyloxan-3-yl] hydrogen sulfate
• 化学式: C₆H₁₂O₈S
• 分子量: 244.222
• InChiKey: MSBDOJFBVRPFGF-VSOAQEOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  15
• 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：
  142
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  6-deoxy-L-galactose 在 硫酸 作用下， 生成 O⁴-sulfo-L-6-deoxy-galactose
  参考文献：
  名称：

  Synthesis of L-fucose 2-, 3-, and 4-Sulphates

  摘要：

  Treatment of L-fucose with an excess pf pyridine-sulphur trioxide gave an equilibrium mixture of mono-, di-, and tri-sulphates. L-Fucose was sulphated under optimal conditions for monosulphate formation, and the monoester fraction was isolated by chromatography on DEAE-cellulose. The isomeric L-fucose 2-, 3-, and 4-sulphates (1-3) were separated on a DEAE-cellulose column by elution with borate buffer. The structures of 1-3 were established by electrophoresis, colour tests, periodate oxidation, and, for the 2-isomer, by comparison with a specimen of 1 that had been definitively synthesised via methyl 3,4-O-isopropylidene-alpha-L-fucopyranoside (6) and methyl alpha-L-fucopyranoside 2-(barium sulphate) (5). The latter was rapidly hydrolysed in hot, dilute acetic acid to 1 and methyl alpha-L-fucopyranoside (4).

  DOI：

  10.1016/s0008-6215(00)83135-3

文献信息

• Synthesis of L-fucose 2-, 3-, and 4-Sulphates
  作者：Peter F. Forrester、Peter F. Lloyd、Charles H. Stuart

  DOI：10.1016/s0008-6215(00)83135-3

  日期：1976.7

  Treatment of L-fucose with an excess pf pyridine-sulphur trioxide gave an equilibrium mixture of mono-, di-, and tri-sulphates. L-Fucose was sulphated under optimal conditions for monosulphate formation, and the monoester fraction was isolated by chromatography on DEAE-cellulose. The isomeric L-fucose 2-, 3-, and 4-sulphates (1-3) were separated on a DEAE-cellulose column by elution with borate buffer. The structures of 1-3 were established by electrophoresis, colour tests, periodate oxidation, and, for the 2-isomer, by comparison with a specimen of 1 that had been definitively synthesised via methyl 3,4-O-isopropylidene-alpha-L-fucopyranoside (6) and methyl alpha-L-fucopyranoside 2-(barium sulphate) (5). The latter was rapidly hydrolysed in hot, dilute acetic acid to 1 and methyl alpha-L-fucopyranoside (4).