methyl 2-O-acetyl-3,4-O-isopropylidene-α-D-galactopyranoside | 197297-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: methyl 2-O-acetyl-3,4-O-isopropylidene-α-D-galactopyranoside
• 英文别名: [(3aS,4R,6S,7R,7aS)-4-(hydroxymethyl)-6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl] acetate
• CAS: 197297-87-3
• 化学式: C₁₂H₂₀O₇
• 分子量: 276.287
• InChiKey: CJEWWMPAFPVKSG-KJPMQGKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-O-acetyl-3,4-O-isopropylidene-α-D-galactopyranoside 在 溶剂黄146 作用下， 反应 0.25h， 生成 methyl 2-O-acetyl-α-D-galactopyranoside
  参考文献：
  名称：

  半乳糖吡喃糖苷的异亚丙基化的新结果。用于合成半乳糖衍生物的有用中间体。

  摘要：

  几种α-和β-吡喃半乳糖苷与2,2-二甲氧基丙烷反应生成多达五种类型的单，双和三（异亚丙基）乙缩醛，其中3,4-0-异亚丙基-6-0 -（2-甲氧基异丙基）衍生物可以高产率获得，并且是用于选择性合成2-，6-和2,6-0-取代的半乳糖衍生物的有用的中间体。

  DOI：

  10.1016/s0040-4039(00)84515-3
• 作为产物：
  描述：

  Methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-α-D-galactopyranoside 在 对甲苯磺酸 吡啶 作用下， 以 甲醇 为溶剂， 反应 0.08h， 生成 methyl 2-O-acetyl-3,4-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  半乳糖吡喃糖苷的异亚丙基化的新结果。用于合成半乳糖衍生物的有用中间体。

  摘要：

  几种α-和β-吡喃半乳糖苷与2,2-二甲氧基丙烷反应生成多达五种类型的单，双和三（异亚丙基）乙缩醛，其中3,4-0-异亚丙基-6-0 -（2-甲氧基异丙基）衍生物可以高产率获得，并且是用于选择性合成2-，6-和2,6-0-取代的半乳糖衍生物的有用的中间体。

  DOI：

  10.1016/s0040-4039(00)84515-3

文献信息

• Lipases in the Regioselective Preparation of Glyceric Acid Esters of Methyl Glycosides
  作者：Riku Sundell、Liisa T. Kanerva

  DOI：10.1002/ejoc.201300450

  日期：2013.8

  lipase-catalyzed regioselective acylation of methyl α-D-galacto-, -gluco- and -mannopyranosides with isopropylidene-protected (R)- and (S)-glyceric acid methyl esters in organic solvents is presented. Factors affecting the formation of the 6-O-mono- and 2,6-O-diacylated products are examined and preparative-scale reactions are detailed. In addition, studies on partially protected methyl α-D-galactopyranosides

  介绍了在有机溶剂中用异亚丙基保护的 (R)-和 (S)-甘油酸甲酯对甲基 α-D-半乳糖-、-葡萄糖-和-吡喃甘露糖苷进行脂肪酶催化的区域选择性酰化。研究了影响 6-O-单酰化和 2,6-O-二酰化产物形成的因素，并详细介绍了制备规模的反应。此外，还介绍了对部分保护的甲基 α-D-吡喃半乳糖苷的研究，其中 3,4-O-异亚丙基保护的化合物即使在高底物浓度下也能专门导致 6-O-单酰化产物的形成。在甲醇中使用酸性树脂可以去除异亚丙基保护基团，而不会干扰 C-6 上的酯键。
• Efficient Differentiation of the Hydroxyl Groups of 3,4-<i>O</i>-Isopropylidene-D-Galactopyranosides by Lipase Catalyzed Esterification and De - Esterification
  作者：Pier Luigi Barili、Giorgio Catelani、Felicia D'Andrea、Ettore Mastrorilli

  DOI：10.1080/07328309708005733

  日期：1997.9

  The Pseudomonas sp. (LPS) promoted acyl transfer from vinyl acetate to selected 3,4-O-isopropylidene-D-galactopyranosides takes place in a completely selective manner giving in high yield the corresponding 6-O-acetates. The acetylation rate is strongly dependent on the type and the orientation of the aglycon, varying from a maximum of reactivity for the 1-deoxy derivative, 1,5-anhydro-3,4-O-isopropylidene-D-galactitol (1d), to a minimum for beta configurated alkyl glycosides and showing a complete loss of reactivity for 3',4':2,3:5,6-tri-O-isopropylidenelactose dimethyl acetal (1e). The latter compound is, however, selectively 6'-O-esterified in good yield by lipase from Candida Antarctica and vinyl acetate. Also the course of the enzymatic hydrolysis of 2,6-di-O-acetyl-3,4-O-isopropylidene-D-galactopyranosides 2 is dependent on the type of the aglycon, both for the reaction rate and the selectivity. The 2-O-acetates 4 are selectively obtained in good yields with porcine pancreatic lipase (PPL) promoted hydrolysis in the case of beta- and alpha-methyl, and 1-deoxy derivatives (2a, 2b and 2d), while for beta-benzyl (2c) and lactose (2e) analogues satisfactory results are obtained with lipase from Mucor miehei (IM20).