Trifluoro-methanesulfonic acid (2S,4aR,6S,7R,8S,8aS)-7-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester | 164322-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: Trifluoro-methanesulfonic acid (2S,4aR,6S,7R,8S,8aS)-7-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
• 英文别名: [(2S,4aR,6S,7R,8S,8aS)-6-methoxy-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] trifluoromethanesulfonate
• CAS: 164322-56-9
• 化学式: C₂₂H₂₃F₃O₈S
• 分子量: 504.481
• InChiKey: ISXGSRYCSGKVSF-SSFAQJFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (2S,4aR,6S,7R,8S,8aS)-7-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 在 吡啶 、 六氟异丙醇 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2R,3R,4E)-1,3-O-Benzylidene-5-(benzyloxy)-2-O-formyl-4-pentene-1,2,3-triol
  参考文献：
  名称：

  Ring Contraction vs Fragmentation in the Intramolecular Reactions of 3-O-(Trifluoromethanesulfonyl)pyranosides. Efficient Synthesis of Branched-Chain Furanosides

  摘要：

  Intramolecular reactions of several methyl 3-O-triflylpyranosides of gluco, manno, galacto, and arabino (2-deoxy-gluco) configuration are studied. Triflates 1b-6b, of gluco, manno, and 8-deoxy-gluco configuration, give rise to ring-contraction products (branched-chain furanosides) 12, 15, 16, 17, 19, and 20, respectively. Triflates 7b and 10b of galacto configuration give the fragmentation products 21 and 23, whereas the 2-deoxy-galacto derivative 8b leads to ring-contraction product 20, which shows the decisive influence of the configuration at position 4 and the presence of a 2-alkoxy group on the reaction process. When the results from 4,6-O-benzylidene derivatives (1b-8b) and 4,6-di-O-benzyl derivatives (91b-11b) are compared, it turns out that the presence of a 4,6-O-benzylidene protecting group favors the formation of ring-contraction products. The use of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as the solvent and pyridine or 2,6-di-tert-butyl-4-methylpyridine as the base allowed us to obtain good to excellent yields of ring-contraction or fragmentation products.

  DOI：

  10.1021/jo00119a011
• 作为产物：
  描述：

  三氟甲磺酸酐 、 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 Trifluoro-methanesulfonic acid (2S,4aR,6S,7R,8S,8aS)-7-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
  参考文献：
  名称：

  Ring Contraction vs Fragmentation in the Intramolecular Reactions of 3-O-(Trifluoromethanesulfonyl)pyranosides. Efficient Synthesis of Branched-Chain Furanosides

  摘要：

  Intramolecular reactions of several methyl 3-O-triflylpyranosides of gluco, manno, galacto, and arabino (2-deoxy-gluco) configuration are studied. Triflates 1b-6b, of gluco, manno, and 8-deoxy-gluco configuration, give rise to ring-contraction products (branched-chain furanosides) 12, 15, 16, 17, 19, and 20, respectively. Triflates 7b and 10b of galacto configuration give the fragmentation products 21 and 23, whereas the 2-deoxy-galacto derivative 8b leads to ring-contraction product 20, which shows the decisive influence of the configuration at position 4 and the presence of a 2-alkoxy group on the reaction process. When the results from 4,6-O-benzylidene derivatives (1b-8b) and 4,6-di-O-benzyl derivatives (91b-11b) are compared, it turns out that the presence of a 4,6-O-benzylidene protecting group favors the formation of ring-contraction products. The use of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as the solvent and pyridine or 2,6-di-tert-butyl-4-methylpyridine as the base allowed us to obtain good to excellent yields of ring-contraction or fragmentation products.

  DOI：

  10.1021/jo00119a011

文献信息

• Ring Contraction vs Fragmentation in the Intramolecular Reactions of 3-O-(Trifluoromethanesulfonyl)pyranosides. Efficient Synthesis of Branched-Chain Furanosides
  作者：Mohamed Kassou、Sergio Castillon

  DOI：10.1021/jo00119a011

  日期：1995.7

  Intramolecular reactions of several methyl 3-O-triflylpyranosides of gluco, manno, galacto, and arabino (2-deoxy-gluco) configuration are studied. Triflates 1b-6b, of gluco, manno, and 8-deoxy-gluco configuration, give rise to ring-contraction products (branched-chain furanosides) 12, 15, 16, 17, 19, and 20, respectively. Triflates 7b and 10b of galacto configuration give the fragmentation products 21 and 23, whereas the 2-deoxy-galacto derivative 8b leads to ring-contraction product 20, which shows the decisive influence of the configuration at position 4 and the presence of a 2-alkoxy group on the reaction process. When the results from 4,6-O-benzylidene derivatives (1b-8b) and 4,6-di-O-benzyl derivatives (91b-11b) are compared, it turns out that the presence of a 4,6-O-benzylidene protecting group favors the formation of ring-contraction products. The use of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as the solvent and pyridine or 2,6-di-tert-butyl-4-methylpyridine as the base allowed us to obtain good to excellent yields of ring-contraction or fragmentation products.