allyl O-(2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-β-D-galactopyranoside | 152773-04-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: allyl O-(2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-β-D-galactopyranoside
• 英文别名: 5-thio-Fuc2Ac3Ac4Ac(a1-2)Gal3Ac4Ac6Ac(b)-O-allyl；[(2R,3S,4S,5R,6R)-3,4-diacetyloxy-6-prop-2-enoxy-5-[(2R,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-methylthian-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 152773-04-1
• 化学式: C₂₇H₃₈O₁₅S
• 分子量: 634.656
• InChiKey: ZEDVXIGOUHFOCL-HVBWILKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  43
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  211
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  allyl O-(2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.25h， 以92%的产率得到allyl O-(5-thio-α-L-fucopyranosyl)-(1->2)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of 5-Thio-l-fucose-Containing Disaccharides, as Sequence-Specific Inhibitors, and 2‘-Fucosyllactose, as a Substrate of α-l-Fucosidases

  摘要：

  Four 5-thio-L-fucose-containing disaccharides having alpha(1-->6), alpha(1-->3), alpha(1-->4)GlcNAc, and alpha(1-->2-Gal linkages (compounds 1-4, respectively) were synthesized as potential alpha-L-fucosidase inhibitors. The glycosylation reactions using 2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate as a glycosyl donor and BF3 . OEt(2) as a catalyst gave mainly alpha-linked disaccharides. Only alpha(1-->2)-linked disaccharide 4 showed inhibitory activity (K-i = 0.21 mM) against Bacillus alpha-L-fucosidase which hydrolyzes the Fuc alpha(1-->2) linkage specifically. The results suggested that sequence specificity of an enzyme could be estimated from the inhibitory activities of the compounds 1-4. In contrast, every disaccharide showed inhibitory activity (K-i = 30-91 mu M) against bovine epididymis alpha-L-fucosidase.

  DOI：

  10.1021/jo961725h
• 作为产物：
  描述：

  2-O-monochloroacetyl acetobromogalactose 在 三氟化硼乙醚 、 氰化汞 作用下， 以 硝基甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 0.25h， 生成 allyl O-(2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Efficient and stereoselective 1,2-cis glycoside formation of 5-thioaldopyranoses: glycosylation with peracetylated 5-thio-D- arabinopyranosyl and 5-thio-L-fucopyranosyl trichloroacetimidates

  摘要：

  Trichloroacetimidate method was proved to be effective for 5-thio-D-arabinopyranosylation and 5-thio-L-fucopyranosylation of N-acetyl-D-glucosaminides and D-galactosides. In these 5-thioglycosylation the neighboring group participation of 2-0-acetyl function was not decisive of anomeric stereoselectivity to give 1,2-cis pseudodisaccharides predominantly. Allyl 2-O-(5-thio-alpha-L-fucopyranosyl)-beta-D-galactopyranoside showed potent inhibitory activity toward alpha-L-fucosidase (Ki = 30muM).

  DOI：

  10.1016/s0040-4039(00)74054-8