methyl 3-O-benzyl-2-O-(2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside | 111490-44-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-benzyl-2-O-(2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside
• CAS: 111490-44-9
• 化学式: C₂₃H₃₄O₁₁
• 分子量: 486.516
• InChiKey: NJVHGKUKPRJHHF-KVOAZWNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.72
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  145.53
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 3-O-benzyl-2-O-(2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside 在 溶剂黄146 作用下， 反应 1.0h， 以97%的产率得到(2R,3S,4S,5R,6R)-2-((2S,3S,4S,5S,6R)-4-Benzyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
  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
• 作为产物：
  描述：

  methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-α-D-mannopyranoside 在 sodium tetrahydroborate 、 molecular sives 3A 、 四丁基氟化铵 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 6.0h， 生成 methyl 3-O-benzyl-2-O-(2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside
  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