4-methylphenyl 2-O-vinyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside | 793672-57-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylphenyl 2-O-vinyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: (2S,3R,4S,5R,6R)-3-ethenoxy-2-(4-methylphenyl)sulfanyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 793672-57-8
• 化学式: C₃₆H₃₈O₅S
• 分子量: 582.761
• InChiKey: QBKJLFSPGFADQJ-GJXDWMKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-methylphenyl 2-O-vinyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 碘 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 26.0h， 生成 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  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 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride sodium methylate 、 sodium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 50.5h， 生成 4-methylphenyl 2-O-vinyl-3,4,6-tri-O-benzyl-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

文献信息

• Stereospecific Synthesis of 1,2-<i>cis</i> Glycosides by Vinyl-Mediated IAD
  作者：Kampanart Chayajarus、David J. Chambers、Majid J. Chughtai、Antony J. Fairbanks

  DOI：10.1021/ol048427o

  日期：2004.10.1

  (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.