propyl 2-O-(α-D-glucopyranosyluronic acid)-3-O-(α-L-fucopyranosyl)-α-L-fucopyranoside sodium salt | 1110650-20-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: propyl 2-O-(α-D-glucopyranosyluronic acid)-3-O-(α-L-fucopyranosyl)-α-L-fucopyranoside sodium salt
• 英文别名: sodium;(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2R,3S,4R,5R,6S)-5-hydroxy-6-methyl-2-propoxy-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxyoxane-2-carboxylate
• CAS: 1110650-20-8
• 化学式: C₂₁H₃₅O₁₅*Na
• 分子量: 550.49
• InChiKey: SOWFLKINVHOABM-VOXAJYLSSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -8.32
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  237
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 、 水 作用下， 反应 2.0h， 以18 mg的产率得到propyl 2-O-(α-D-glucopyranosyluronic acid)-3-O-(α-L-fucopyranosyl)-α-L-fucopyranoside sodium salt
  参考文献：
  名称：

  Stereoselective Synthesis of Di- and Trisaccharide Fucoidan Fragments Bearing α-D-Glucuronic Acid Residue∗

  摘要：

  The first stereoselective synthesis of disaccharide alpha-D-GlcA-(1 -> 2)-alpha-L-Fuc-OPr ( 1), trisaccharide (1 -> 3)-alpha-L-Fuc-[alpha-D-GlcA-(1 -> 2)]-alpha-L-Fuc-OPr(3), and their selectively O-sulfated derivatives 2 and 4 bearing sulfo-groups at O(4) of the fucose units has been performed. Compounds 1-4 represent the fragments of the chain of the fucoidan from Cladosiphon okamuranus brown seaweed. Glucuronylation by a series of selectively O-acetylated glucuronyl bromides was studied to obtain the target products. It has been found that 3-O-acetylated donor 6 is the most efficient agent for alpha-glycoside bond formation that can be connected with intramolecular remote participation of 3-O-acetyl group favoring alpha-stereoselectivity.

  DOI：

  10.1080/07328300802419865