methyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside | 131293-00-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-2-(hydroxymethyl)-6-methylsulfanyloxan-3-yl] benzoate
• CAS: 131293-00-0
• 化学式: C₂₈H₂₆O₈S
• 分子量: 522.576
• InChiKey: DHJWSUWNUGQFTP-NRUNVSGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside 、 methyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 在 三氟甲磺酸酐 、 亚碘酰苯 、 4 A molecular sieve 作用下， 以 乙腈 为溶剂， 以99%的产率得到
  参考文献：
  名称：

  Iodosobenzene-triflic anhydride as an efficient promoter for glycosidation reaction using thioglycosides as donors

  摘要：

  A reagent prepared in situ from iodosobenzene (PhIO) and trifluoromethanesulfonic anhydride (Tf2O) was successfully applied to the activation of thioglycosides. Glycosidation with benzyl-protected methyl thioglycosides as glycosyl donors proceeded smoothly under mild reaction conditions. The same reagent also promoted glycosidation with less reactive acylated methyl thioglycosides in the presence of silica gel to form 1, 2-trans glycosides.

  DOI：

  10.1016/s0040-4039(00)60863-8

文献信息

• Garegg, Per J.; Oscarson, Stefan; Kvarnstroem, Ingemar, Acta Chemica Scandinavica, 1990, vol. 44, # 6, p. 625 - 629
  作者：Garegg, Per J.、Oscarson, Stefan、Kvarnstroem, Ingemar、Niklasson, Annika、Niklasson, Gunilla、et al.

  DOI：——

  日期：——
• GAREGG, PER J.;OSCARSON, STEFAN;KVARNSTROM, INGEMAR;NIKLASSON, ANNIKA;NIK+, ACTA CHEM. SCAND., 44,(1990) N, C. 625-629
  作者：GAREGG, PER J.、OSCARSON, STEFAN、KVARNSTROM, INGEMAR、NIKLASSON, ANNIKA、NIK+

  DOI：——

  日期：——
• Iodosobenzene-triflic anhydride as an efficient promoter for glycosidation reaction using thioglycosides as donors
  作者：Koichi Fukase、Atsushi Hasuoka、Ikuko Kinoshita、Shoichi Kusumoto

  DOI：10.1016/s0040-4039(00)60863-8

  日期：1992.11

  A reagent prepared in situ from iodosobenzene (PhIO) and trifluoromethanesulfonic anhydride (Tf2O) was successfully applied to the activation of thioglycosides. Glycosidation with benzyl-protected methyl thioglycosides as glycosyl donors proceeded smoothly under mild reaction conditions. The same reagent also promoted glycosidation with less reactive acylated methyl thioglycosides in the presence of silica gel to form 1, 2-trans glycosides.