phenyl 2,3,4-tri-O-benzyl-6-O-[2-(diphenylmethylaminocarbonyl)benzoyl]-1-thio-α-D-glucopyranoside

• 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: phenyl 2,3,4-tri-O-benzyl-6-O-[2-(diphenylmethylaminocarbonyl)benzoyl]-1-thio-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-phenylsulfanyloxan-2-yl]methyl 2-(benzhydrylcarbamoyl)benzoate
• 化学式: C₅₄H₄₉NO₇S
• 分子量: 856.052
• InChiKey: FXZYWXOFFIIAHT-WIPXCJIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  63
• 可旋转键数：
  19
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-tri-O-benzyl-6-O-[2-(diphenylmethylaminocarbonyl)benzoyl]-1-thio-α-D-glucopyranoside 、 甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 在 三氟甲磺酸三甲基硅酯 、 亚碘酰苯 作用下， 以 various solvent(s) 为溶剂， 反应 1.5h， 以53%的产率得到methyl 2,3,4-O-tri-benzyl-6-O-[2-(diphenylmethylaminocarbonyl)benzoyl]-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective glycosylation using the long-range effect of a [2-(4-phenylbenzyl)oxycarbonyl]benzoyl group

  摘要：

  Highly alpha-selective glucosylation was effected by virtue of the solvent effect of cyclopentyl methyl ether and the long-range assistance of bulky 6-O-protective groups. Higher alpha-selectivity was obtained by the use of this solvent in comparison to conventional diethyl ether. alpha-Selectivity was further improved with the influence of 6-O-substituents, such as TBDPS and phthaloyl groups, the latter being mono esterified with a bulky alcohol. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.042
• 作为产物：
  描述：

  、 二苯甲胺 在 4-二甲氨基吡啶 达卡巴嗪 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到phenyl 2,3,4-tri-O-benzyl-6-O-[2-(diphenylmethylaminocarbonyl)benzoyl]-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective glycosylation using the long-range effect of a [2-(4-phenylbenzyl)oxycarbonyl]benzoyl group

  摘要：

  Highly alpha-selective glucosylation was effected by virtue of the solvent effect of cyclopentyl methyl ether and the long-range assistance of bulky 6-O-protective groups. Higher alpha-selectivity was obtained by the use of this solvent in comparison to conventional diethyl ether. alpha-Selectivity was further improved with the influence of 6-O-substituents, such as TBDPS and phthaloyl groups, the latter being mono esterified with a bulky alcohol. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.042

文献信息

• Stereoselective glycosylation using the long-range effect of a [2-(4-phenylbenzyl)oxycarbonyl]benzoyl group
  作者：Hiroomi Tokimoto、Yukari Fujimoto、Koichi Fukase、Shoichi Kusumoto

  DOI：10.1016/j.tetasy.2004.11.042

  日期：2005.1

  Highly alpha-selective glucosylation was effected by virtue of the solvent effect of cyclopentyl methyl ether and the long-range assistance of bulky 6-O-protective groups. Higher alpha-selectivity was obtained by the use of this solvent in comparison to conventional diethyl ether. alpha-Selectivity was further improved with the influence of 6-O-substituents, such as TBDPS and phthaloyl groups, the latter being mono esterified with a bulky alcohol. (C) 2004 Elsevier Ltd. All rights reserved.