allyl 4-O-acetyl-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyluronate)-α-L-fucopyranoside | 1110650-28-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 4-O-acetyl-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyluronate)-α-L-fucopyranoside
• CAS: 1110650-28-6
• 化学式: C₃₉H₄₆O₁₂
• 分子量: 706.787
• InChiKey: FDYRIKUIBJIIQT-NWUPAACMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  51.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  137.44
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3-O-acetyl-4-O-benzoyl-2-O-benzyl-L-fucopyranosyl trichloroacetimidate 、 allyl 4-O-acetyl-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyluronate)-α-L-fucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到allyl 4-O-acetyl-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyluronate)-3-O-(2-O-benzyl-3-O-acetyl-4-O-benzoyl-α-L-fucopyranosyl)-α-L-fucopyranoside
  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
• 作为产物：
  描述：

  allyl 2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyluronate)-α-L-fucopyranoside 、 原乙酸三乙酯 在 对甲苯磺酸 、 水 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以90%的产率得到allyl 4-O-acetyl-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyluronate)-α-L-fucopyranoside
  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