3-O-(6-O-tert-butyldimethylsilyl-β-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol | 887700-86-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(6-O-tert-butyldimethylsilyl-β-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol
• CAS: 887700-86-9
• 化学式: C₁₈H₃₆O₈Si
• 分子量: 408.565
• InChiKey: QAGRTMCNGZXLDU-VNAATALASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  106.84
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-O-(6-O-tert-butyldimethylsilyl-β-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol 在 四丁基氟化铵 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 3-O-(2,3,4-tri-O-benzyl-β-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol
  参考文献：
  名称：

  Syntheses of an α-d-Gal-(1→6)-β-d-Gal diglyceride, as lipase substrate

  摘要：

  Two different routes were explored to afford 3-O-(6-0-alpha-D-galactopyranosyl-beta-D-galactopyranosyl)-1,2-di-O-dodecanoyl-sn-glycerol. In the first one, the key step was the glycosylation of the 3-O-(2,3,4-tri-O-benzyl-beta-D-galactopyranosyl)- 1, 2-O-isopropylidene-sn-glycerol acceptor with 2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside as the donor. In the second one, the key step was the coupling of 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-D-galactopyranosyl trichloroacetimidate donor with 1,2-O-isopropylidene-sn-glycerol. Even though the number of steps was the same in both pathways, the first one afforded a better overall yield (12.4%) than the second one (6.5%). This eight-step synthesis allowed the preparation of the expected glycolipid, which was used as substrate for recombinant GPLRP2 galactolipase using the monomolecular film technique. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.021
• 作为产物：
  描述：

  2',3',4',6'-tetra-O-acetyl-1'-O-β-D-galactopyranosyl-(2S,3)-isopropylidene-glycerol 在 咪唑 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-O-(6-O-tert-butyldimethylsilyl-β-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol
  参考文献：
  名称：

  Syntheses of an α-d-Gal-(1→6)-β-d-Gal diglyceride, as lipase substrate

  摘要：

  Two different routes were explored to afford 3-O-(6-0-alpha-D-galactopyranosyl-beta-D-galactopyranosyl)-1,2-di-O-dodecanoyl-sn-glycerol. In the first one, the key step was the glycosylation of the 3-O-(2,3,4-tri-O-benzyl-beta-D-galactopyranosyl)- 1, 2-O-isopropylidene-sn-glycerol acceptor with 2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside as the donor. In the second one, the key step was the coupling of 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-D-galactopyranosyl trichloroacetimidate donor with 1,2-O-isopropylidene-sn-glycerol. Even though the number of steps was the same in both pathways, the first one afforded a better overall yield (12.4%) than the second one (6.5%). This eight-step synthesis allowed the preparation of the expected glycolipid, which was used as substrate for recombinant GPLRP2 galactolipase using the monomolecular film technique. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.021