ethyl 3-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside | 863997-27-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside
• 英文别名: [(2S,3R,4R,5R,6R)-3-azido-2-ethylsulfanyl-5-hydroxy-6-(hydroxymethyl)oxan-4-yl] acetate
• CAS: 863997-27-7
• 化学式: C₁₀H₁₇N₃O₅S
• 分子量: 291.328
• InChiKey: VYGUHDXJXYUJBC-SPFKKGSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 3-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside 在 吡啶 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 为溶剂， 反应 41.0h， 生成 ethyl 3,4-di-O-acetyl-2-azido-2-deoxy-6-O-[methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosyl)onate]-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：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-(allyloxycarbonylamino)-β-D-glucopyranose 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 三氟甲磺酸酐 、 triflic azide 、 三氟化硼乙醚 、 sodium 、 对甲苯磺酸 、 乙硫醇 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 56.0h， 生成 ethyl 3-O-acetyl-2-azido-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