tert-butyldimethylsilyl 3-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside | 863997-28-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyldimethylsilyl 3-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside
• 英文别名: [(2S,3R,4R,5R,6R)-3-azido-2-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl] acetate
• CAS: 863997-28-8
• 化学式: C₁₄H₂₇N₃O₆Si
• 分子量: 361.47
• InChiKey: HWBKKJNENRKVLO-LBELIVKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  99.6
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyl 3-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside 在 吡啶 、 甲磺酰溴 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.5h， 生成 tert-butyldimethylsilyl 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-α-D-galacto-2-nonulopyranosyl)onate]-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：

  tert-butyldimethylsilyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以59%的产率得到tert-butyldimethylsilyl 3-O-acetyl-2-azido-2-deoxy-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