phenyl 2,3-di-O-pivaloyl-4-O-benzyl-1-thio-α-D-mannopyranoside | 1319152-57-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3-di-O-pivaloyl-4-O-benzyl-1-thio-α-D-mannopyranoside
• 英文别名: pivaloyl(-2)[pivaloyl(-3)][Bn(-4)]Man(a)-SPh；[(2R,3R,4S,5S,6R)-5-(2,2-dimethylpropanoyloxy)-2-(hydroxymethyl)-3-phenylmethoxy-6-phenylsulfanyloxan-4-yl] 2,2-dimethylpropanoate
• CAS: 1319152-57-2
• 化学式: C₂₉H₃₈O₇S
• 分子量: 530.683
• InChiKey: MXUNZIFFHBIIFZ-WJGLBBAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 2,3-di-O-pivaloyl-4-O-benzyl-1-thio-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-pivaloyl-4-O-benzyl-α-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Experimental observations on the regioselectivity of glycosylation of a 4,6-diol system in the β-d-mannopyranosyl unit of a N-glycan pentasaccharide core structure

  摘要：

  The regioselectivity of glycosylation of a 4,6-diol system in the p-mannopyranosyl unit of a N-glycan pentasaccharide core structure is found to be strongly dependent on the structure of the glycosyl donor. While glycosylation with a 2-O-acetyl-D-mannopyranosyl trichloroacetimidate and with a D-mannopyranosyl (alpha 1 -> 3) 2-O-acetyl mannopyranosyl trichoroacetimidate regioselectively occurs at the primary OH-6 position, reaction with D-mannopyranosyl (alpha 1 -> 6) mannopyranosyl 2-O-benzoyl, 2-O-acetyl and 2-O-pivaloyl trichloroacetimidate results in approximately 1:1 mixture of regioisomers at primary OH-6 and secondary OH-4 positions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.006
• 作为产物：
  描述：

  phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.08h， 生成 phenyl 2,3-di-O-pivaloyl-4-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Experimental observations on the regioselectivity of glycosylation of a 4,6-diol system in the β-d-mannopyranosyl unit of a N-glycan pentasaccharide core structure

  摘要：

  The regioselectivity of glycosylation of a 4,6-diol system in the p-mannopyranosyl unit of a N-glycan pentasaccharide core structure is found to be strongly dependent on the structure of the glycosyl donor. While glycosylation with a 2-O-acetyl-D-mannopyranosyl trichloroacetimidate and with a D-mannopyranosyl (alpha 1 -> 3) 2-O-acetyl mannopyranosyl trichoroacetimidate regioselectively occurs at the primary OH-6 position, reaction with D-mannopyranosyl (alpha 1 -> 6) mannopyranosyl 2-O-benzoyl, 2-O-acetyl and 2-O-pivaloyl trichloroacetimidate results in approximately 1:1 mixture of regioisomers at primary OH-6 and secondary OH-4 positions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.006

文献信息

• Experimental observations on the regioselectivity of glycosylation of a 4,6-diol system in the β-d-mannopyranosyl unit of a N-glycan pentasaccharide core structure
  作者：Nerea Ruiz、Sandra S. Ferreira、Daniel Padro、Niels-C. Reichardt、Manuel Martín-Lomas

  DOI：10.1016/j.carres.2011.05.006

  日期：2011.9

  The regioselectivity of glycosylation of a 4,6-diol system in the p-mannopyranosyl unit of a N-glycan pentasaccharide core structure is found to be strongly dependent on the structure of the glycosyl donor. While glycosylation with a 2-O-acetyl-D-mannopyranosyl trichloroacetimidate and with a D-mannopyranosyl (alpha 1 -> 3) 2-O-acetyl mannopyranosyl trichoroacetimidate regioselectively occurs at the primary OH-6 position, reaction with D-mannopyranosyl (alpha 1 -> 6) mannopyranosyl 2-O-benzoyl, 2-O-acetyl and 2-O-pivaloyl trichloroacetimidate results in approximately 1:1 mixture of regioisomers at primary OH-6 and secondary OH-4 positions. (C) 2011 Elsevier Ltd. All rights reserved.