(2S,3R,4S,5R,6R)-3,4-Bis-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran | 58369-08-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5R,6R)-3,4-Bis-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran
• CAS: 58369-08-7
• 化学式: C₂₇H₃₄O₆
• 分子量: 454.563
• InChiKey: JECJDMXORBIOJU-SEFGFODJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  33.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R,6R)-3,4-Bis-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran 在 sodium hydroxide 、 potassium tert-butylate 、 sodium methylate 、 四丁基硫酸氢铵 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 methyl 2,3-anhydro-4,6-di-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis, crystalline structure, conformational analysis, and azidolysis of methyl 2,3-anhydro-α-d-manno- and -allo-pyranoside p-bromobenzyl

  摘要：

  Methyl 2,3-anhydro-4,6-di-O-p-bromobenzyl-alpha-D-allopyranoside (6) was synthesized from methyl 4,6-O-benzylidene-alpha-D-glucopyranoside (1) via the intermediate methyl 4,6-di-O-p-bromobenzyl-2,3-di-O-p-tolylsulfonyl-alpha-D-glucopyranoside. Treatment of 6 with sodium azide selectively afforded methyl 3-azido-4,6-di-O-p-bromobenzyl-3-deoxy-alpha-D-glucopyranoside in 70% yield. Methyl 2,3-anhydro-4,6-di-O-p-bromobenzyl-(17) and methyl 2,3-anhydro-4,6-di-O-benzyl-alpha-D-mannopyranoside (18) were obtained from 1 via the intermediates methyl 4,6-di-O-p-bromobenzyl- and methyl 4,6-di-O-benzyl-2-O-p-tolylsulfonyl-alpha-D-glucopyranoside. Azidolysis of 17 and 18 with sodium azide in the presence of tetraethylammonium chloride in N,N-dimethylformamide gave the respective 3-azidoaltropyransides, in yields of 80%, by exclusive 3-attack. The crystal structure of compound 6 is orthorhombic with a space group of P2(1)2(1)2(1), and the 2,3-anhydropyranose moiety is in an almost ideal degrees-H-5 half-chair conformation. The crystals of 17 are also orthorhombic, belonging to space group P2(1)2(1)2(1), but the conformation is a hybrid of the degrees-H-5 half-chair and the degrees-E sofa. Analysis by NMR spectroscopy suggests that in solution in CDCl3 the conformation of 17 remains the same as, and that of 6 undergoes a change from, the respective solid-state conformations.

  DOI：

  10.1016/0008-6215(92)80086-g