benzyl 2-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranoside | 63283-86-3

• 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: benzyl 2-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranoside
• 英文别名: [(3aS,4R,6R,7R,7aS)-4-(hydroxymethyl)-2,2-dimethyl-6-phenylmethoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl] acetate
• CAS: 63283-86-3
• 化学式: C₁₈H₂₄O₇
• 分子量: 352.384
• InChiKey: CSBBGEMFXGSGHJ-DRRXZNNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  benzyl 2-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranoside 在 Dowex DR-2030 作用下， 生成 benzyl 2-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  通过 NMR 光谱和动力学计算研究选择性保护的 β-d-吡喃半乳糖苷中的酰基迁移和裂解

  摘要：

  通过NMR光谱研究了一系列β-d-吡喃半乳糖的乙酰基、新戊酰基和苯甲酰基保护基团的迁移及其在可变pH下的相对稳定性。不同酯基的顺时针和逆时针迁移速率通过使用动力学模型准确确定。所呈现的结果为常用酯保护基团的酸碱稳定性和酰基迁移现象提供了新的见解，并可能有助于规划合成策略。

  DOI：

  10.1021/ja801177s
• 作为产物：
  描述：

  苄基Beta-D-吡喃半乳糖苷 在 四丁基氟化铵 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 103.5h， 生成 benzyl 2-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Selectively protected galactose derivatives for the synthesis of branched oligosaccharides

  摘要：

  Synthesis and characterization of several new anomerically pure galactose derivatives, based on simple and effective protective group manipulations of benzyl beta-D-galactopyranoside, are reported. The monosaccharides described contain selectively protected/deprotected hydroxyl functionalities at their 1,2,3,4- and 6-positions rendering them useful as building blocks for construction of branched oligosaccharides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.054

文献信息

• 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).
• KRISTEN, HELMUT;VOGEL, CHRISTIAN;STEFFAN, WOLFRAM;ANDREJ, YA;BETANELI, VI+
  作者：KRISTEN, HELMUT、VOGEL, CHRISTIAN、STEFFAN, WOLFRAM、ANDREJ, YA、BETANELI, VI+

  DOI：——

  日期：——