ethyl 2-allyloxycarbonylamino-2-deoxy-3,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside | 863997-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-allyloxycarbonylamino-2-deoxy-3,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside
• CAS: 863997-30-2
• 化学式: C₂₂H₃₇NO₈S
• 分子量: 475.604
• InChiKey: LWORPQNYJNZRRN-HHARLNAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  120.39
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-allyloxycarbonylamino-2-deoxy-3,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 sodium hydroxide 、 三氟甲磺酸酐 、 triflic azide 、 三氟化硼乙醚 、 对甲苯磺酸 、 乙硫醇 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 50.0h， 生成 ethyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  An alternative high yielding and highly stereoselective method for preparing an α-Neu5NAc-(2,6)-d-GalN3 building block suitable for further glycosylation

  摘要：

  This paper deals with new approaches to alpha-Neu5NAc-(2,6)-D-GalN(3) building blocks, suitable as glycosylation donors. The major improvement, by comparison with the results of the literature, lies in the glycosylation step of a new D-galactosamine acceptor (tert-butyldimethylsilyl 3-O-acetyl-2-azido-2-deoxy-beta-D-galactopyranoside) with O-methyl-S-[methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranosyl)onate] dithiocarbonate as the N-acetylneuraminic acid donor. The reaction affords the expected disaccharide in high yield (85%) and a complete alpha-Neu5NAc stereoselectivity. A subsequent oxidation step, eliminating the glycal by-product allows an easier purification. Afterwards, the tert-butyldimethylsilyl disaccharide can be transformed into a donor, after cleavage of the anomeric group in smooth conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.05.007
• 作为产物：
  描述：

  ethyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-1-thio-β-D-glucopyranoside 在 吡啶 、 sodium 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 ethyl 2-allyloxycarbonylamino-2-deoxy-3,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  An alternative high yielding and highly stereoselective method for preparing an α-Neu5NAc-(2,6)-d-GalN3 building block suitable for further glycosylation

  摘要：

  This paper deals with new approaches to alpha-Neu5NAc-(2,6)-D-GalN(3) building blocks, suitable as glycosylation donors. The major improvement, by comparison with the results of the literature, lies in the glycosylation step of a new D-galactosamine acceptor (tert-butyldimethylsilyl 3-O-acetyl-2-azido-2-deoxy-beta-D-galactopyranoside) with O-methyl-S-[methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranosyl)onate] dithiocarbonate as the N-acetylneuraminic acid donor. The reaction affords the expected disaccharide in high yield (85%) and a complete alpha-Neu5NAc stereoselectivity. A subsequent oxidation step, eliminating the glycal by-product allows an easier purification. Afterwards, the tert-butyldimethylsilyl disaccharide can be transformed into a donor, after cleavage of the anomeric group in smooth conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.05.007