butyl 2-deoxy-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: butyl 2-deoxy-α-D-glucopyranoside
• 英文别名: butyl 2-deoxy-D-glucopyranoside；(2R,3S,4R,6S)-6-butoxy-2-(hydroxymethyl)oxane-3,4-diol
• 化学式: C₁₀H₂₀O₅
• 分子量: 220.266
• InChiKey: UIJLROKKIOYBSL-IMSYWVGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 sodium acetate buffer 、 Aspergillus niger α-glucosidase 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 butyl 2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Enzymatic synthesis of alkyl α-2-deoxyglucosides by alkyl alcohol resistant α-glucosidase from Aspergillus niger

  摘要：

  Aspergillus niger alpha-glucosidase (ANGase) was used for an efficient syntheses of alkyl alpha-D-2-deoxyglucosides (A2DGs) and for regioselectivity studies of alkoxy-hydro additions Of D-glucal in the presence of alkyl alcohols. ANGase showed a high stability with respect to the high concentration of alkyl alcohols. The reaction conditions were optimized for pH, temperature, alkyl alcohol concentration, and D-glucal concentration. On the basis of MS and NMR analyses, A2DGs were confirmed to have only an alpha-2deoxyglucosidic bond and the two-dimensional NMR (HMBC) spectra showed to be made up of 2-deoxyglucosyl and alkyl moieties. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.046

文献信息

• TBAF Effects 3,6-Anhydro Formation from 6-<i>O</i>-Tosyl Pyranosides
  作者：Zachary A. Morrison、Mark Nitz

  DOI：10.1021/acs.orglett.0c00045

  日期：2020.2.21

  3,6-Anhydro sugars are common structures in algal polysaccharides and occur in the furanodictine and sauropunol natural products. We have found that treatment of 6-O-tosylpyranosides with tetrabutylammonium fluoride provides a mild, high-yielding synthesis of 3,6-anhydro sugars. Using O-glycoside substrates, 3,6-anhydropyranosides are isolated and the use of N,O-dimethyl hydroxylamine glycosides yields

  3,6-脱水糖是藻类多糖中的常见结构，并存在于呋喃达克丁和sauropunol天然产物中。我们发现用氟化四丁基铵处理6-O-甲苯磺酰基吡喃糖苷提供了温和的，高产率的3，6-脱水糖的合成。使用O-糖苷底物，分离出3，6-脱水吡喃糖苷，并且使用N，O-二甲基羟胺糖苷产生3，6-脱水呋喃糖苷。据报道，采用这种方法，可以合成几种3,6-脱水糖天然产物的简捷合成路线，包括呋喃果苦碱A和sauropunols AD。