3-O-tert-butyldimethylsilyl-L-fucal | 101915-61-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-O-tert-butyldimethylsilyl-L-fucal
• 英文别名: (2S,3R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-2-methyl-3,4-dihydro-2H-pyran-3-ol
• CAS: 101915-61-1
• 化学式: C₁₂H₂₄O₃Si
• 分子量: 244.406
• InChiKey: UJOBWNWTDACYCC-GARJFASQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-O-tert-butyldimethylsilyl-L-fucal 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 4-O-tert-butyldimethylsilyl-L-fucal
  参考文献：
  名称：

  Selective silylation of 6-deoxyglycals

  摘要：

  DOI：

  10.1016/s0008-6215(00)90680-3
• 作为产物：
  描述：

  2,6-脱水-1,5-二脱氧-L-阿拉伯-己-5-烯糖二乙酸酯 在 咪唑 、 甲醇 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.25h， 生成 3-O-tert-butyldimethylsilyl-L-fucal
  参考文献：
  名称：

  Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide

  摘要：

  The first synthesis of the tetrasaccharide fragment of the anthracycline natural product Arugomycin is described. A reagent controlled dehydrative glycosylation method involving cyclopropenium activation was utilized to synthesize the alpha-linkages with complete anomeric selectivity. The synthesis was completed in 20 total steps, and in 2.5% overall yield with a longest linear sequence of 15 steps.

  DOI：

  10.1021/acs.orglett.0c01153

文献信息

• Umpolung Reactivity in the Stereoselective Synthesis of S-Linked 2-Deoxyglycosides
  作者：Kedar N. Baryal、Danyang Zhu、Xiaohua Li、Jianglong Zhu

  DOI：10.1002/anie.201301682

  日期：2013.7.29

  Take control! An unprecedented sulfenylation of stereochemically defined 2‐deoxyglycosyl lithium species with asymmetric sugar‐derived disulfide acceptors enabled the stereoselective synthesis of both α‐ and β‐S‐linked 2‐deoxyoligosaccharides. Reductive lithiation of 2‐deoxyglycosyl phenylsulfides at −78 °C provides predominantly axial glycosyl lithium species, which upon warming isomerize to predominantly

  控制住！立体化学定义的2-脱氧糖基锂物种与不对称糖衍生的二硫键受体的前所未有的亚磺酰化作用，使得立体选择性合成α-和β-S-连接的2-脱氧寡糖成为可能。在−78°C下2-脱氧糖基苯基硫化物的还原锂化作用主要提供了轴向糖基锂物质，该物质在升温时异构化为主要为赤道的锂物质（请参见方案）。
• Direct Synthesis of 2-Deoxy-β-Glycosides via Anomeric <i>O</i>-Alkylation with Secondary Electrophiles
  作者：Danyang Zhu、Kedar N. Baryal、Surya Adhikari、Jianglong Zhu

  DOI：10.1021/ja4116956

  日期：2014.2.26

  An approach for direct synthesis of biologically significant 2-deoxy-beta-glycosides has been developed via O-alkylation of a variety of 2-deoxy-sugar-derived anomeric alkoxides using challenging secondary triflates as electrophiles. It was found a free hydroxyl group at C3 of the 2-deoxy-sugar-derived lactols is required in order to achieve synthetically efficient yields. This method has also been applied to the convergent synthesis of a 2-deoxy-beta-tetrasaccharide.
• Automated, Multistep Continuous‐Flow Synthesis of 2,6‐Dideoxy and 3‐Amino‐2,3,6‐trideoxy Monosaccharide Building Blocks
  作者：Subbarao Yalamanchili、Tu‐Anh Nguyen、Alexander Zsikla、Gavin Stamper、Ashley E. DeYong、John Florek、Olivea Vasquez、Nicola L. B. Pohl、Clay S. Bennett

  DOI：10.1002/anie.202109887

  日期：2021.10.18

  AbstractAn automated continuous flow system capable of producing protected deoxy‐sugar donors from commercial material is described. Four 2,6‐dideoxy and two 3‐amino‐2,3,6‐trideoxy sugars with orthogonal protecting groups were synthesized in 11–32 % overall yields in 74–131.5 minutes of total reaction time. Several of the reactions were able to be concatenated into a continuous process, avoiding the need for chromatographic purification of intermediates. The modular nature of the experimental setup allowed for reaction streams to be split into different lines for the parallel synthesis of multiple donors. Further, the continuous flow processes were fully automated and described through the design of an open‐source Python‐controlled automation platform.