methyl α-L-talopyranoside | 1219125-11-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl α-L-talopyranoside
• 英文别名: (2S,3S,4R,5R,6R)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol
• CAS: 1219125-11-7
• 化学式: C₇H₁₄O₆
• 分子量: 194.185
• InChiKey: HOVAGTYPODGVJG-CQOGJGKDSA-N

物化性质

• 沸点：
  389.1±42.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl α-L-talopyranoside 、 三氟乙酸酐 、 二氯甲烷 生成 [(2S,3S,4R,5R,6R)-6-methoxy-3,4,5-tris[(2,2,2-trifluoroacetyl)oxy]oxan-2-yl]methyl 2,2,2-trifluoroacetate
  参考文献：
  名称：

  KONIG, WILFRIED A.;MISCHNICK-LUBBECKE, PETRA;BRASSAT, BARBEL;LUTZ, SABINE+, CARBOHYDR. RES., 183,(1988) N 1, C. 11-17

  摘要：

  DOI：
• 作为产物：
  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