methyl 3-O-allyl-4,6-O-benzylidene-α-D-galactopyranoside | 161168-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 3-O-allyl-4,6-O-benzylidene-α-D-galactopyranoside
• 英文别名: (2S,4aR,6S,7R,8R,8aS)-6-methoxy-2-phenyl-8-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 161168-93-0
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: ASPVDBYGHHICFR-JHMPBIJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 、 methyl 3-O-allyl-4,6-O-benzylidene-α-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙醚 为溶剂， 以63%的产率得到methyl 3-O-allyl-4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-galactopyranoside
  参考文献：
  名称：

  The synthesis of 2-, 3-, 4- and 6-O-α-d-glucopyranosyl-d-galactopyranose, and their evaluation as nutritional supplements for pre-term infants

  摘要：

  Four methods have been screened for the synthesis of some alpha-D-glucopyrano sides, with the recently reported (Mukaiyama) combination of 2,3,4,6-tetra-O-benzyl- alpha-D-glucopyranosyl iodide and triphenylphosphine oxide being the most successful, especially in the diastereoselectivity exhibited. The alpha-D-glueopyranosides so obtained have been deprotected to yield 2-, 3-, 4- and 6-O-alpha-D-glucopyranosyl-D-galactopyranose. Only the last disaccharide showed any hydrolysis by alpha-glycosidases but this success was not emulated by mucosal extracts from the small intestine of the pig. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.04.022
• 作为产物：
  描述：

  苯甲醛二乙缩醛 、 methyl 3-O-allyl-α-D-galactopyranoside 在 camphor-10-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以68%的产率得到methyl 3-O-allyl-4,6-O-benzylidene-α-D-galactopyranoside
  参考文献：
  名称：

  The synthesis of 2-, 3-, 4- and 6-O-α-d-glucopyranosyl-d-galactopyranose, and their evaluation as nutritional supplements for pre-term infants

  摘要：

  Four methods have been screened for the synthesis of some alpha-D-glucopyrano sides, with the recently reported (Mukaiyama) combination of 2,3,4,6-tetra-O-benzyl- alpha-D-glucopyranosyl iodide and triphenylphosphine oxide being the most successful, especially in the diastereoselectivity exhibited. The alpha-D-glueopyranosides so obtained have been deprotected to yield 2-, 3-, 4- and 6-O-alpha-D-glucopyranosyl-D-galactopyranose. Only the last disaccharide showed any hydrolysis by alpha-glycosidases but this success was not emulated by mucosal extracts from the small intestine of the pig. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.04.022

文献信息

• Monoalkylation of Tributyltin Activated Methyl 4,6-<i>O</i>-Benzylidene-α-D-gluco- and -galactopyranosides
  作者：Falguni Dasgupta、Per J. Garegg

  DOI：10.1055/s-1994-25649

  日期：——

  Monoalkylation of methyl 4,6-O-benzylidene-α-D-gluco- and galactopyranosides could be carried out in good yields using bis(tributyltin) oxide. Regioselectivity, giving predominant 2-substitution, was excellent in the case of D-glucopyranoside. The ratio of the tin reagent to that of the substrate seems to be critical in determining the yield and the extent of regioselectivity. Alkylation could also be carried out in solvents at a slower rate, using less reagent, but the regioselectivity was lower.

  使用双（三丁基氧化锡）可对甲基 4,6-O-亚苄基-δ-D-吡喃葡萄糖苷和吡喃半乳糖苷进行单烷基化反应，产量很高。在 D-吡喃葡萄糖苷的情况下，区域选择性非常好，主要是 2-取代。锡试剂与底物的比例似乎是决定产率和区域选择性程度的关键。烷基化也可以在溶剂中进行，速度较慢，使用的试剂较少，但区域选择性较低。