methyl 2,3-dideoxy-α-L-threo-hex-2-enopyranoside | 1219031-05-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl 2,3-dideoxy-α-L-threo-hex-2-enopyranoside
• 英文别名: (2S,3S,6R)-2-(hydroxymethyl)-6-methoxy-3,6-dihydro-2H-pyran-3-ol
• CAS: 1219031-05-6
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: BDSSJXGPGYQORZ-LYFYHCNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,3-dideoxy-α-L-threo-hex-2-enopyranoside 在 四氧化锇 、 四甲基乙二胺 、 乙二胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以80%的产率得到methyl α-L-talopyranoside
  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
• 作为产物：
  描述：

  methyl 6-O-acetyl-4-O-benzyl-2,3-dideoxy-α-L-threo-hex-2-enopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以98%的产率得到methyl 2,3-dideoxy-α-L-threo-hex-2-enopyranoside
  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