1,5-Anhydro-6-O-benzoyl-2,3-di-O-benzyl-D-glucitol | 176168-91-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,5-Anhydro-6-O-benzoyl-2,3-di-O-benzyl-D-glucitol
• CAS: 176168-91-5
• 化学式: C₂₇H₂₈O₆
• 分子量: 448.516
• InChiKey: ABNOMFJWEQZJKW-XDZVQPMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,5-Anhydro-6-O-benzoyl-2,3-di-O-benzyl-D-glucitol 在 4 A molecular sieve 、 sodium methylate 、 DMTST 作用下， 以 甲醇 、 苯 为溶剂， 反应 38.0h， 生成 [(2R,3R,4R,5S)-4,5-Bis-benzyloxy-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-methanol
  参考文献：
  名称：

  Synthetic Studies on Sialoglycoconjugates 81: Synthesis of Positional Isomers of Sialyl Lewis X Epitope Containing 1-Deoxy-dGlucose in Place ofN-Acetylglucosamine, and Their Inhibitory Activity to Selectin-Mediated Adhesion

  摘要：

  Three sialyl-Le(X) epitope analogs, which carry fucose and alpha-sialyl-(2-->3)galactose residues at O-2 and O-3, O-3 and O-2, and O-4 and O-6 positions of 1-deoxy-D-glucose backbone, respectively, have been synthesized. Glycosylation of 1,5-anhydro-4,6-O-benzylidene-D-glucitol (1) or 1,5-anhydro-6-O-benzoyl-2,3-di-O-benzyl-D-glucitol (4) prepared from 1,5-anhydro-D-glucitol, with methyl 2,3,4-tri-O-benzyl- 1-thio-beta-L-fucopyranoside (5) using dimethyl(methylthio)sulfonium triflate (DMTST) as a promoter, afforded the corresponding fucosyl 1,5-anhydro-D-glucitol derivatives 7, 8 and 9. Glycosylation of 7, 8 or 10 derived from 9, with methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonate)-(2-->3)-2,4,6-tri-O- 1-thio-beta-D-galactopyranoside (11) in the presence of DMTST gave the expected tetrasaccharide derivatives 12, 16 and 20. Hydrolysis of the benzylidene group in 12 and 16 gave compounds 13 and 17. Finally 13, 17 and 20 were transformed, by reductive removal of the benzyl groups, O-deacylation and subsequent hydrolysis of the methyl ester, into the sialyl-Le(X) epitope analogs 15, 19 and 22, respectively.

  DOI：

  10.1080/07328309608005435
• 作为产物：
  描述：

  1,5-anhydro-2,3-di-O-benzyl-4,6-O-benzylidene-D-glucitol 在 吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 1,5-Anhydro-6-O-benzoyl-2,3-di-O-benzyl-D-glucitol
  参考文献：
  名称：

  Synthetic Studies on Sialoglycoconjugates 81: Synthesis of Positional Isomers of Sialyl Lewis X Epitope Containing 1-Deoxy-dGlucose in Place ofN-Acetylglucosamine, and Their Inhibitory Activity to Selectin-Mediated Adhesion

  摘要：

  Three sialyl-Le(X) epitope analogs, which carry fucose and alpha-sialyl-(2-->3)galactose residues at O-2 and O-3, O-3 and O-2, and O-4 and O-6 positions of 1-deoxy-D-glucose backbone, respectively, have been synthesized. Glycosylation of 1,5-anhydro-4,6-O-benzylidene-D-glucitol (1) or 1,5-anhydro-6-O-benzoyl-2,3-di-O-benzyl-D-glucitol (4) prepared from 1,5-anhydro-D-glucitol, with methyl 2,3,4-tri-O-benzyl- 1-thio-beta-L-fucopyranoside (5) using dimethyl(methylthio)sulfonium triflate (DMTST) as a promoter, afforded the corresponding fucosyl 1,5-anhydro-D-glucitol derivatives 7, 8 and 9. Glycosylation of 7, 8 or 10 derived from 9, with methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonate)-(2-->3)-2,4,6-tri-O- 1-thio-beta-D-galactopyranoside (11) in the presence of DMTST gave the expected tetrasaccharide derivatives 12, 16 and 20. Hydrolysis of the benzylidene group in 12 and 16 gave compounds 13 and 17. Finally 13, 17 and 20 were transformed, by reductive removal of the benzyl groups, O-deacylation and subsequent hydrolysis of the methyl ester, into the sialyl-Le(X) epitope analogs 15, 19 and 22, respectively.

  DOI：

  10.1080/07328309608005435