allyl 3-O-acetyl-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyluronate)-4-O-(2-O-benzyl-3-O-acetyl-4-O-benzoyl-α-L-fucopyranosyl)-α-L-fucopyranoside | 1110650-27-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3-O-acetyl-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyluronate)-4-O-(2-O-benzyl-3-O-acetyl-4-O-benzoyl-α-L-fucopyranosyl)-α-L-fucopyranoside
• CAS: 1110650-27-5
• 化学式: C₆₁H₆₈O₁₈
• 分子量: 1089.2
• InChiKey: NJAYQXDOIJBLEH-YHISALKRSA-N

反应信息

• 作为产物：
  描述：

  、 乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以20 mg的产率得到allyl 3-O-acetyl-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyluronate)-4-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