methyl 4,6-O-benzylidene-β-D-glucopyranoside | 401812-53-1

• 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 4,6-O-benzylidene-β-D-glucopyranoside
• 英文别名: methyl 4,6-benzylidene-β-D-glucopyranoside；(2S,4aR,6R,7R,8R,8aS)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 401812-53-1
• 化学式: C₁₄H₁₈O₆
• 分子量: 282.293
• InChiKey: VVSWDMJYIDBTMV-UCKQBZRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-β-D-glucopyranoside 在 sodium dodecyl-sulfate 、 溴甲苯 作用下， 以 水 为溶剂， 反应 14.0h， 以90%的产率得到甲基 Β-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Nascent-HBr催化去除水性表面活性剂中的正交保护基。

  摘要：

  在水环境中的有机反应最近已成为有前途的研究领域。首次描述了由分散的催化剂苄基溴的缓慢水解生成的新生HBr，其中内部水存在于含水表面活性剂中的受限胶束介质的疏水核中。持续释放的新生HBr能够以良好或极好的收率对碳水化合物，氨基醇和羟基化无环化合物中存在的酸敏感性正交官能团进行化学选择性切割。

  DOI：

  10.1021/acs.joc.9b02561

文献信息

• SYNTHESIS AND CONFORMATIONAL INVESTIGATIONS OF SULFATED CARBOHYDRATES1
  作者：Katrin Probst、Hans Wessel

  DOI：10.1081/car-100108273

  日期：——

  Starting from the finding that methyl 2,3,4,6-tetra-O-sulfonato-beta -D-glucopyranoside (3) existed in a conformational equilibrium of the two chair conformers, the effect of sulfation on conformational equilibria was further investigated using a number of sulfated saccharides. Three sulfate groups on positions 3,4, and 6 or two on positions 2 and 3 were not sufficient to induce the conformational change as shown with methyl 2-amino-2-deoxy-3,4,6-tri-O-sulfonato-beta -D-glucopyranoside. N-Sulfation of the amino group of the latter compound furnished an equilibrium of chair conformers with less (1)C(4) con-former content than for 3. The presence of persulfated methyl P-D-galactopyranoside in the usual (4)C(1) conformation suggested the involvement of the 4-O-sulfate in the effect. Methyl 2,3,4-tri-O-sulfonato-beta -D-xylopyranoside was found to prefer the "all-axial" (1)C(4) conformation demonstrating that O-sulfates facilitate 1,3-O/O-diaxial interactions better than ester groups and in particular benzoates. Also, sulfated 1,5-anhydro-D-glucitol occurred as a conformational mixture, the influence of the anomeric effect may thus have been overestimated in the previous discussion of this conformational effect.
• Nascent-HBr-Catalyzed Removal of Orthogonal Protecting Groups in Aqueous Surfactants
  作者：Shilpi Gupta、Smritilekha Bera、Dhananjoy Mondal

  DOI：10.1021/acs.joc.9b02561

  日期：2020.2.21

  the hydrophobic core of the confined micellar medium in aqueous surfactant is described for the first time. The sustained-release nascent-HBr enabled the chemoselective cleavages of acid-sensitive orthogonal functionalities present in carbohydrates, amino alcohols, and hydroxylated acyclic compounds in good to excellent yields.

  在水环境中的有机反应最近已成为有前途的研究领域。首次描述了由分散的催化剂苄基溴的缓慢水解生成的新生HBr，其中内部水存在于含水表面活性剂中的受限胶束介质的疏水核中。持续释放的新生HBr能够以良好或极好的收率对碳水化合物，氨基醇和羟基化无环化合物中存在的酸敏感性正交官能团进行化学选择性切割。