3,4,5,7-tetra-O-benzyl-α-D-manno-hept-2-ulopyranose 3',4',5',7'-tetra-O-benzyl-α-D-manno-hept-2'-ulopyranose 1,2':2,1'-dianhydride | 388570-22-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,5,7-tetra-O-benzyl-α-D-manno-hept-2-ulopyranose 3',4',5',7'-tetra-O-benzyl-α-D-manno-hept-2'-ulopyranose 1,2':2,1'-dianhydride
• 英文别名: (1S,2S,3R,4R,6S,9S,10S,11S,12R,13R)-1,2,3,10,11,12-hexakis(phenylmethoxy)-4,13-bis(phenylmethoxymethyl)-5,8,14,16-tetraoxadispiro[5.2.59.26]hexadecane
• CAS: 388570-22-7
• 化学式: C₇₀H₇₂O₁₂
• 分子量: 1105.33
• InChiKey: VQZBMGMEWVCEKG-VAAVPFOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  82
• 可旋转键数：
  26
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3,4,5,7-tetra-O-benzyl-α-D-manno-hept-2-ulopyranose 3',4',5',7'-tetra-O-benzyl-α-D-manno-hept-2'-ulopyranose 1,2':2,1'-dianhydride 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 12.0h， 生成 α-D-manno-hept-2-ulopyranose α-D-manno-hept-2'-ulopyranose 1,2':2,1'-dianhydride
  参考文献：
  名称：

  Stereoselective synthesis and structure elucidation of spiro-ketodisaccharides

  摘要：

  Cycloglycosylation of 3,4,5,7-tetra-O-benzyl-alpha -D-hept-2-ulopyranoses (2a-c) was carried out stereoselectively under the catalysis of Lewis acid to afford two spiro-cyclodisaccharides 3a-c and 4a-c in good yields. The reaction provided the kinetic products 3a-c or the thermodynamic products 4a-c as the predominant products under different conditions, respectively. The unprotected disaccharides 5a-c and 6a-c and the acetylated derivatives 7a-c and 5a-c were prepared by catalytic hydrogenation and followed by acetylation. The structures of compounds 4a-c, 6a-c and 8a-c were confirmed to be alpha,beta -anomeric configuration with chair-chair-chair forin for the tri-cycles based on the X-ray crystallographic analysis of 6a-c. The alpha,alpha -anomeric configurations of compounds 3a-c, 5a-c and 7a-c were determined based on the measurements of the three bond coupling constants (3)J(C,H) between the C-1 and the H-3 of 7a-c. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00775-x
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-1-deoxy-1-methylidene-D-mannopyranose 在 四氧化锇 、 potassium trifluoromethansulfonate 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 乙醚 、 丙酮 、 叔丁醇 为溶剂， 反应 5.0h， 生成 3,4,5,7-tetra-O-benzyl-α-D-manno-hept-2-ulopyranose 3',4',5',7'-tetra-O-benzyl-α-D-manno-hept-2'-ulopyranose 1,2':2,1'-dianhydride
  参考文献：
  名称：

  Stereoselective synthesis and structure elucidation of spiro-ketodisaccharides

  摘要：

  Cycloglycosylation of 3,4,5,7-tetra-O-benzyl-alpha -D-hept-2-ulopyranoses (2a-c) was carried out stereoselectively under the catalysis of Lewis acid to afford two spiro-cyclodisaccharides 3a-c and 4a-c in good yields. The reaction provided the kinetic products 3a-c or the thermodynamic products 4a-c as the predominant products under different conditions, respectively. The unprotected disaccharides 5a-c and 6a-c and the acetylated derivatives 7a-c and 5a-c were prepared by catalytic hydrogenation and followed by acetylation. The structures of compounds 4a-c, 6a-c and 8a-c were confirmed to be alpha,beta -anomeric configuration with chair-chair-chair forin for the tri-cycles based on the X-ray crystallographic analysis of 6a-c. The alpha,alpha -anomeric configurations of compounds 3a-c, 5a-c and 7a-c were determined based on the measurements of the three bond coupling constants (3)J(C,H) between the C-1 and the H-3 of 7a-c. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00775-x

文献信息

• Stereoselective synthesis and structure elucidation of spiro-ketodisaccharides
  作者：Xiaoliu Li、Hideyo Takahashi、Hiro Ohtake、Moto Shiro、Shiro Ikegami

  DOI：10.1016/s0040-4020(01)00775-x

  日期：2001.9

  Cycloglycosylation of 3,4,5,7-tetra-O-benzyl-alpha -D-hept-2-ulopyranoses (2a-c) was carried out stereoselectively under the catalysis of Lewis acid to afford two spiro-cyclodisaccharides 3a-c and 4a-c in good yields. The reaction provided the kinetic products 3a-c or the thermodynamic products 4a-c as the predominant products under different conditions, respectively. The unprotected disaccharides 5a-c and 6a-c and the acetylated derivatives 7a-c and 5a-c were prepared by catalytic hydrogenation and followed by acetylation. The structures of compounds 4a-c, 6a-c and 8a-c were confirmed to be alpha,beta -anomeric configuration with chair-chair-chair forin for the tri-cycles based on the X-ray crystallographic analysis of 6a-c. The alpha,alpha -anomeric configurations of compounds 3a-c, 5a-c and 7a-c were determined based on the measurements of the three bond coupling constants (3)J(C,H) between the C-1 and the H-3 of 7a-c. (C) 2001 Elsevier Science Ltd. All rights reserved.