4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranos-4-O-yl)ethyl)-1-thio-β-D-glucopyranoside | 793672-65-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranos-4-O-yl)ethyl)-1-thio-β-D-glucopyranoside
• CAS: 793672-65-8
• 化学式: C₆₄H₆₉IO₁₁S
• 分子量: 1173.22
• InChiKey: URVQOOZLFSZDNS-JAQIEUPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.49
• 重原子数：
  77.0
• 可旋转键数：
  28.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  101.53
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranos-4-O-yl)ethyl)-1-thio-β-D-glucopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 碘 、 silver trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以33%的产率得到methyl 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Stereospecific Synthesis of 1,2-cis Glycosides by Vinyl-Mediated IAD

  摘要：

  (GRAPHICS)Stereospecific 1,2-cis glycosylation of 2-O-vinyl thioglycosides, synthesized from the corresponding alcohols by Ir-catalyzed transvinylation with vinyl acetate, is achieved by iodine-mediated tethering of a range of primary and secondary carbohydrate acceptors, followed by intramolecular aglycon delivery (IAD). The use of such an intramolecular glycosylation strategy furnishes the desired alpha-gluco and beta-manno disaccharides in an entirely stereoselective manner.

  DOI：

  10.1021/ol048427o
• 作为产物：
  描述：

  4-methylphenyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 2,6-二叔丁基-4-甲基吡啶 、 碘 、 silver trifluoromethanesulfonate 、 sodium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 50.0h， 生成 4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranos-4-O-yl)ethyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Stereospecific Synthesis of 1,2-cis Glycosides by Vinyl-Mediated IAD

  摘要：

  (GRAPHICS)Stereospecific 1,2-cis glycosylation of 2-O-vinyl thioglycosides, synthesized from the corresponding alcohols by Ir-catalyzed transvinylation with vinyl acetate, is achieved by iodine-mediated tethering of a range of primary and secondary carbohydrate acceptors, followed by intramolecular aglycon delivery (IAD). The use of such an intramolecular glycosylation strategy furnishes the desired alpha-gluco and beta-manno disaccharides in an entirely stereoselective manner.

  DOI：

  10.1021/ol048427o