methyl 4-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glycopyranosyl)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside | 1256155-22-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glycopyranosyl)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside
• 英文别名: Bn(-2)Glc3Ac4Ac6Ac(a1-4)[Bz(-2)][Bz(-3)][Bz(-6)]a-Glc1Me；[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-3-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-phenylmethoxyoxan-2-yl]oxy-6-methoxyoxan-2-yl]methyl benzoate
• CAS: 1256155-22-2
• 化学式: C₄₇H₄₈O₁₇
• 分子量: 884.888
• InChiKey: RPHLKOMIWPGRLR-NAMJJXJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  64
• 可旋转键数：
  23
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  204
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside 、 2-thiazolinyl 2-O-benzyl-3,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside 在 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 生成 methyl 4-O-(3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glycopyranosyl)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside 、 methyl 4-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glycopyranosyl)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  On the stereoselectivity of glycosidation of thiocyanates, thioimidates, and thioglycosides

  摘要：

  Comparative side-by-side glycosylation studies demonstrated that glycosyl thiocyanates, thioimidates, and thioglycosides provide comparative stereoselectivities in glycosylations. Very high alpha-stereoselectivity that was previously recorded for glycosyl thiocyanates can be achieved, but only if glycosyl acceptors are equipped with electron-withdrawing acyl substituents. Partially benzylated glycosyl acceptors provided relatively modest stereoselectivity, which was on a par with other common glycosyl donors. Accordingly, thioimidates and thioglycosides showed high stereoselectivity similarly to that of thiocyanates with different classes of acylated primary and secondary glycosyl acceptors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.08.003