α-L-Fucp-(1,2)-β-D-Galp-(1)-4-methylumbelliferone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: α-L-Fucp-(1,2)-β-D-Galp-(1)-4-methylumbelliferone
• 英文别名: 4-Methylumbelliferyl 2-O-(alpha-L-fucopyranosyl)-beta-D-galactopyranoside；7-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4-methylchromen-2-one
• 化学式: C₂₂H₂₈O₁₂
• 分子量: 484.457
• InChiKey: QVEUSHJADSGABK-WAPVNEFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  185
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  4-methylumbelliferyl 3',4',6'-tri-O-acetyl-2'-O-(2'',3'',4''-tri-O-acetyl-α-L-fucopyranosyl)-β-D-galactopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 0.5h， 以62%的产率得到α-L-Fucp-(1,2)-β-D-Galp-(1)-4-methylumbelliferone
  参考文献：
  名称：

  Stereoselective synthesis of α-L-Fucp-(1,2)- and -(1,3)-β-D-Galp(1)-4-methylumbelliferone using glycosyl donor substituted by propane-1,3-diyl phosphate as leaving group

  摘要：

  合成双糖α-L-岩藻糖-(1,2)-和α-L-岩藻糖-(1,3)-β-D-半乳糖-(1)-4-甲基伞花素作为岩藻糖苷酶底物，通过用TMSOTf激活2,3,4-三-O-乙酰基和2,3,4,6-四-O-乙酰基α,β-L-岩藻糖和-D-半乳糖基丙烷-1,3-二醇磷酸盐的异头中心，并对4-甲基伞花素β-D-半乳糖苷进行了最小保护。

  DOI：

  10.1039/b002754p

文献信息

• Synthesis of fucosidase substrates using propane-1,3-diyl phosphate as the anomeric leaving group
  作者：Hariprasad Vankayalapati、Gurdial Singh

  DOI：10.1016/s0040-4039(99)00571-7

  日期：1999.5

  Activation of the anomeric centre of suitably protected L-fucopyranose and D-galactopyranose with propane-1,3-diyl phosphate allowed the synthesis of the disaccharide alpha-L-Fucp-(1,2)-beta-D-Galp(1)-4-methylumbelliferone as a fucosidase substrate. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Stereoselective synthesis of α-L-Fucp-(1,2)- and -(1,3)-β-D-Galp(1)-4-methylumbelliferone using glycosyl donor substituted by propane-1,3-diyl phosphate as leaving group
  作者：Hariprasad Vankayalapati、Gurdial Singh

  DOI：10.1039/b002754p

  日期：——

  The synthesis of the disaccharides α-L-Fucp-(1,2)- and α-L-Fucp-(1,3)-β-D-Galp(1)-4-methylumbelliferone as fucosidase substrates was accomplished by activation of the anomeric centre of 2,3,4-tri-O-acetyl- and 2,3,4,6-tetra-O-acetyl-α,β-L-fuco- and -D-galactopyranosyl propane-1,3-diyl phosphates with TMSOTf and with minimal protection of 4-methylumbelliferyl β-D-galactopyranoside.

  合成双糖α-L-岩藻糖-(1,2)-和α-L-岩藻糖-(1,3)-β-D-半乳糖-(1)-4-甲基伞花素作为岩藻糖苷酶底物，通过用TMSOTf激活2,3,4-三-O-乙酰基和2,3,4,6-四-O-乙酰基α,β-L-岩藻糖和-D-半乳糖基丙烷-1,3-二醇磷酸盐的异头中心，并对4-甲基伞花素β-D-半乳糖苷进行了最小保护。