methyl 3,4-di-O-acetyl-2-O-benzyl-α-D-glucopyranosyluronate bromide | 1110650-22-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-acetyl-2-O-benzyl-α-D-glucopyranosyluronate bromide
• 英文别名: methyl (2S,3S,4S,5R,6R)-3,4-diacetyloxy-6-bromo-5-phenylmethoxyoxane-2-carboxylate
• CAS: 1110650-22-0
• 化学式: C₁₈H₂₁BrO₈
• 分子量: 445.264
• InChiKey: IYPGQTLJFWTMOR-KSWRQPAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3,4-di-O-acetyl-2-O-benzyl-α-D-glucopyranosyluronate bromide 、 allyl 3,4-O-isopropylidene-α-L-fucopyranoside 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 allyl 3,4-O-isopropylidene-2-O-(methyl 3,4-di-O-acetyl-2-O-benzyl-β-D-glucopyranosyluronate)-α-L-fucopyranoside 、 allyl 3,4-O-isopropylidene-2-O-(methyl 3,4-di-O-acetyl-2-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
• 作为产物：
  描述：

  乙酸酐 、 Methyl 2,3,4-tri-O-benzyl-1-bromo-1-deoxy-D-glucopyranuronate 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以59%的产率得到methyl 3-O-acetyl-2,4-di-O-benzyl-α-D-glucopyranosyluronate bromide
  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