(2R,3S,4S,5R,6R)-2-[(2S,3S,4S,5R,6R)-4,5-二羟基-6-(羟基甲基)-2-甲氧基四氢吡喃-3-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇 | 111462-59-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2R,3S,4S,5R,6R)-2-[(2S,3S,4S,5R,6R)-4,5-二羟基-6-(羟基甲基)-2-甲氧基四氢吡喃-3-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
• 英文名称: methyl 2-O-α-D-talopyranosyl-α-D-talopyranoside
• 英文别名: Methyl 2-O-talopyranosyltalopyranoside；(2R,3S,4S,5R,6R)-2-[(2S,3S,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 111462-59-0
• 化学式: C₁₃H₂₄O₁₁
• 分子量: 356.327
• InChiKey: YUAFWDJFJCEDHL-KCMHCVLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside 在 palladium on activated charcoal 咪唑 、 sodium tetrahydroborate 、 molecular sives 3A 、 四丁基氟化铵 、 氢气 、 sodium methylate 、 对甲苯磺酸 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 60.0 ℃ 、345.0 kPa 条件下， 反应 28.0h， 生成 (2R,3S,4S,5R,6R)-2-[(2S,3S,4S,5R,6R)-4,5-二羟基-6-(羟基甲基)-2-甲氧基四氢吡喃-3-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
  参考文献：
  名称：

  Synthesis of methyl 2-O-α--mannopyranosyl-α-d-talopyranoside and methyl 2-O-α-d-talopyranosyl-α-d-talopyranoside

  摘要：

  Treatment of methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D- mannopyranoside (1) with tert-butyldiphenylsilyl chloride in N,N-dimethylformamide afforded methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(2,3,4,6-tetra-O-acetyl -alpha-D- mannopyranosyl)-alpha-D-mannopyranoside (2). Oxidation of 2 with pyridinium chlorochromate, followed by reduction of the carbonyl group, and subsequent O-deacetylation afforded methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-alpha-D-mannopyranosyl- alpha-D- talopyranoside (5). Cleavage of the tert-butyldiphenylsilyl group of 5 with tetrabutylammonium fluoride in oxolane, followed by hydrogenolysis, gave methyl 2-O-alpha-D-mannopyranosyl-alpha-D-talopyranoside (7). O-Deacetylation of 1 gave methyl 3-O-benzyl-2-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside (8). Treatment of 8 with tert-butyldiphenylsilyl chloride afforded a 6,6'-disilyl derivative, which was converted into a 2',3'-O-isopropylidene derivative, and then further oxidized with pyridinium chlorochromate. The resulting diketone was reduced and removal of the protecting groups gave methyl 2-O-alpha-D-talopyranosyl-alpha-D-talopyranoside (15). The structures of both 7 and 15 were established by 13C-n.m.r. spectroscopy.

  DOI：

  10.1016/0008-6215(87)84003-x