methyl 5-C-acetoxymethyl-1,3,4-tetra-O-acetyl-5-deoxy-β-L-xylo-hex-2-ulopyranoside | 231286-57-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 5-C-acetoxymethyl-1,3,4-tetra-O-acetyl-5-deoxy-β-L-xylo-hex-2-ulopyranoside
• 英文别名: [(3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-6-methoxyoxan-3-yl]methyl acetate
• CAS: 231286-57-0
• 化学式: C₁₆H₂₄O₁₀
• 分子量: 376.361
• InChiKey: PLMTXWLXQPBECU-XUWVNRHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 5-C-acetoxymethyl-1,3,4-tetra-O-acetyl-5-deoxy-β-L-xylo-hex-2-ulopyranoside 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 methyl 1,3,4-tri-O-benzyl-5-C-benzyloxymethyl-β-L-xylo-hex-2-ulopyranoside
  参考文献：
  名称：

  Enzymatic Synthesis of a Branched-Chain Hexulose: 5-Deoxy-5-C-hydroxymethyl-β-L-xylo-hex-2-ulopyranose

  摘要：

  The coupling of dihydroxyacetone phosphate with 3- hydroxy-2-(hydroxymethyl)propanal (1) in the presence of rabbit muscle aldolase afforded a branched-chain hexulose phosphate isolated in 64% yield as the barium salt 3. The parent, dephosphorylated sugar 4 was converted to its anhydro derivative 8 and glycoside 9.

  DOI：

  10.1002/(sici)1099-0690(199906)1999:6<1415::aid-ejoc1415>3.0.co;2-2
• 作为产物：
  描述：

  5-deoxy-5-C-hydroxymethyl-β-L-xylo-hex-2-ulopyranose 1-phosphate 在 氢氧化钾 、 (H+) ion exchange resin 、 wheat germ phosphatase 、 水 作用下， 反应 168096.0h， 生成 methyl 5-C-acetoxymethyl-1,3,4-tetra-O-acetyl-5-deoxy-β-L-xylo-hex-2-ulopyranoside
  参考文献：
  名称：

  Enzymatic Synthesis of a Branched-Chain Hexulose: 5-Deoxy-5-C-hydroxymethyl-β-L-xylo-hex-2-ulopyranose

  摘要：

  The coupling of dihydroxyacetone phosphate with 3- hydroxy-2-(hydroxymethyl)propanal (1) in the presence of rabbit muscle aldolase afforded a branched-chain hexulose phosphate isolated in 64% yield as the barium salt 3. The parent, dephosphorylated sugar 4 was converted to its anhydro derivative 8 and glycoside 9.

  DOI：

  10.1002/(sici)1099-0690(199906)1999:6<1415::aid-ejoc1415>3.0.co;2-2