3,4,5,7-tetra-O-benzyl-α-D-gluco-hept-2-ulopyranose 3',4',5',7'-tetra-O-benzyl-β-D-gluco-hept-2'-ulopyranose 1,2':2,1'-dianhydride | 350484-76-3

• 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-gluco-hept-2-ulopyranose 3',4',5',7'-tetra-O-benzyl-β-D-gluco-hept-2'-ulopyranose 1,2':2,1'-dianhydride
• 英文别名: 3,4,5,7-Tetra-O-benzyl-α-D-gluco-heptulopyranose 3',4',5',7'-tetra-O-benzyl-β-D-gluco-heptulopyranose 1,2':1',2-dianhydride；(1R,2S,3R,4R,6R,9S,10R,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: 350484-76-3
• 化学式: C₇₀H₇₂O₁₂
• 分子量: 1105.33
• InChiKey: VQZBMGMEWVCEKG-HDFSVNRKSA-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-gluco-hept-2-ulopyranose 3',4',5',7'-tetra-O-benzyl-β-D-gluco-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-gluco-hept-2-ulopyranose β-D-gluco-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：

  3,4,5,7-tetra-O-benzyl-α-D-gluco-hept-2-ulopyranose 在 三氟甲磺酸钠 、 对甲苯磺酸 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 3,4,5,7-tetra-O-benzyl-α-D-gluco-hept-2-ulopyranose 3',4',5',7'-tetra-O-benzyl-β-D-gluco-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

• Chemical Synthesis of Linear and Cyclic Unnatural Oligosaccharides by Iterative Glycosidation of Ketoses
  作者：Alessandro Dondoni、Alberto Marra、Marie-Christine Scherrmann、Valerio Bertolasi

  DOI：10.1002/1521-3765(20010401)7:7<1371::aid-chem1371>3.0.co;2-j

  日期：2001.4.1

  the isolated oligomers ranged from 48 % in the first cycle to 29% in the fourth cycle. Having employed a pentenyl-substituted hydroxymethylketoside acceptor in the first cycle, all the derived oligomers contained the pentenyl group at their reducing end. This group was exploited to transform the linear oligomers into cyclic products through intramolecular glycosidation. The major product derived from

  描述了立体选择性合成 alpha-D-(2-->1)-连接的酮苷低聚物的有效方法的开发。该方法基于由两个关键步骤组成的迭代方案：a) 噻唑基酮基亚磷酸酯供体与羟甲基酮苷受体的偶联；b) 在所得低聚物的异头碳原子上引入羟甲基。为了突出其效率，该协议被用于通过 alpha-(2-->1) 连接到五聚体阶段的 D-galacto-2-heptulopyranose 低聚酮苷的组装。分离出的低聚物的产率范围从第一个循环的 48% 到第四个循环的 29%。在第一个循环中使用了戊烯基取代的羟甲基酮苷受体，所有衍生的低聚物在其还原端都含有戊烯基。该组被利用通过分子内糖苷化将线性低聚物转化为环状产物。X 射线晶体学证实源自线性三糖的主要产物是环三-(2-->1)-(α-D-galacto-2-heptulopyranosyl)。该化合物的结构基本上是带有三个吡喃半乳糖环的 [9] 冠 - 3 醚的结构，以
• 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.