methyl 6-O-acetyl-4-O-benzyl-α-L-gulopyranoside | 1219031-06-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-acetyl-4-O-benzyl-α-L-gulopyranoside
• CAS: 1219031-06-7
• 化学式: C₁₆H₂₂O₇
• 分子量: 326.346
• InChiKey: PLSBQSISVYGZHR-ZVDSWSACSA-N

反应信息

• 作为产物：
  描述：

  methyl 6-O-acetyl-4-O-benzyl-2,3-dideoxy-α-L-threo-hex-2-enopyranoside 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到methyl 6-O-acetyl-4-O-benzyl-α-L-gulopyranoside
  参考文献：
  名称：

  Highly Stereoselective de Novo Synthesis of l-Hexoses

  摘要：

  An efficient and general de novo synthetic route to enantiomerically pure L-hexoses has been accomplished starting from the heterocyclic homologating agent 5,6-dihydro-1,4-dithiin-2-yl[(4-methoxybentyl)oxy]methane and methyl alpha,beta-isopropylidene-L-glycerate. The sugar scaffold was constructed by an acid-catalyzed domino reaction, which enabled selective preparation of either methyl 2,3-dideoxy-alpha-L-threohex-2-enopyranosides or 1,6-anhydro-2,3-dideoxy-beta-L-threo-hex-2-enopyranose as key intermediates. The subsequent double bond functionalization by syn or anti dihydroxylation reactions allowed introduction of the remaining stereogenic centers, leading to desired orthogonally protected L-hexopyranosides with a high degree of diastereoselectivity and with very good overall yields. These and previous results (based on the use of the corresponding L-erythro epimers) contribute to make our approach general and place it among the few methods able to synthesize the whole series of the rare L-hexoses.

  DOI：

  10.1021/jo100077k