3,4,5,7-tetra-O-benzyl-α-D-galacto-hept-2-ulopyranose | 388570-20-5

• 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-galacto-hept-2-ulopyranose
• 英文别名: (2S,3R,4S,5S,6R)-2-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol
• CAS: 388570-20-5
• 化学式: C₃₅H₃₈O₇
• 分子量: 570.683
• InChiKey: WGFUUMQJBZIOKC-NVCPMKERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4,5,7-tetra-O-benzyl-α-D-galacto-hept-2-ulopyranose 在 sodium tetrahydroborate 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 、 臭氧 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 ((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-2,6-bis-benzyloxymethyl-tetrahydro-pyran-2-yl)-methanol
  参考文献：
  名称：

  α(1-3)-Galactosyltransferase Inhibition Based on a New Type of Disubstrate Analogue This work was supported financially by the Deutschen Forschungsgemeinschaft and the Fonds der Chemischen Industrie.

  摘要：

  How do retaining glycosyltransferases function? To answer this question, UDP-Gal and galactose were covalently linked to form disubstrate analogues 1, of which surprisingly 1β and not 1α inhibited α(1-3)-galactosyltransferases very well. An understanding of this inhibition is a key to the pharmacological prevention of hyperacute rejection in pig to primate xenotransplantation.

  DOI：

  10.1002/1521-3773(20011105)40:21<4007::aid-anie4007>3.0.co;2-f
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-1-deoxy-1-methylidene-D-galactopyranose 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 丙酮 、 叔丁醇 为溶剂， 以93.8%的产率得到3,4,5,7-tetra-O-benzyl-α-D-galacto-hept-2-ulopyranose
  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.
• α(1-3)-Galactosyltransferase Inhibition Based on a New Type of Disubstrate Analogue This work was supported financially by the Deutschen Forschungsgemeinschaft and the Fonds der Chemischen Industrie.
  作者：Bernhard Waldscheck、Markus Streiff、Wolfgang Notz、Willy Kinzy、Richard R. Schmidt

  DOI：10.1002/1521-3773(20011105)40:21<4007::aid-anie4007>3.0.co;2-f

  日期：2001.11.5

  How do retaining glycosyltransferases function? To answer this question, UDP-Gal and galactose were covalently linked to form disubstrate analogues 1, of which surprisingly 1β and not 1α inhibited α(1-3)-galactosyltransferases very well. An understanding of this inhibition is a key to the pharmacological prevention of hyperacute rejection in pig to primate xenotransplantation.