4-O-acetyl-L-rhodinopyranose | 64447-72-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 4-O-acetyl-L-rhodinopyranose
• 英文别名: 4-O-acetyl-L-rhodinose；O-Acetylrhodiose；O-Acetylrhodinose；(4S,5S)-4-O-acetyl-2,3,6-trideoxy-hexopyranose；4-OAc-L-rhodinose；[(2S,3S)-6-hydroxy-2-methyloxan-3-yl] acetate
• CAS: 64447-72-9；64447-83-2
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: NNWBJOVUTCFRGH-CJORJKIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-O-acetyl-L-rhodinopyranose 在 四氮唑 、 lithium hydroxide 、 4 A molecular sieve 、 trimethoxonium tetrafluoroborate 、 N,N-二乙基亚磷酰胺二叔丁酯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 Acetic acid (2S,3R,6S)-2-methyl-6-{(2S,3S,6S)-2-methyl-6-[(2S,3S,6S)-2-methyl-6-(3,3,9-trimethyl-1,5-dioxa-spiro[5.5]undec-9-yloxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yloxy}-3,6-dihydro-2H-pyran-3-yl ester
  参考文献：
  名称：

  Application of Glycosyltetrazoles in Oligosaccharide Synthesis:  Assembly of the C3 Trisaccharide Component of the Antibiotic PI-080

  摘要：

  DOI：

  10.1021/jo951954o
• 作为产物：
  描述：

  Acetic acid (1S,2S)-1-[2-((4S,5S)-4,5-diphenyl-[1,3]dioxolan-2-yl)-ethyl]-2-hydroxy-propyl ester 在 palladium dihydroxide 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 4-O-acetyl-L-rhodinopyranose
  参考文献：
  名称：

  Synthesis of via a tandem sharpless asymmetric dihydroxylation/lipase-catalyzed transesterification

  摘要：

  An enantioselective synthesis of the trideoxy sugar 4-O-acetyl-L-rhodinopyranose (7) is described. A key feature of the synthetic strategy is a Sharpless asymmetric dihydroxylation followed by a lipase-mediated mono-esterification of the resultant diol (3-->4-->6).

  DOI：

  10.1016/0040-4039(95)00778-b

文献信息

• 2,3,6-Trideoxy sugar nucleotides: synthesis and stability
  作者：Mingxuan Wu、Qingqing Meng、Min Ge、Linquan Bai、Huchen Zhou

  DOI：10.1016/j.tetlet.2011.08.132

  日期：2011.11

  The synthesis and characterization of highly challenging 2,3,6-trideoxy sugar nucleotides were described for the first time. The study of their hydrolysis kinetics in aqueous buffers provided insight into their application as glycosyl donors. (C) 2011 Elsevier Ltd. All rights reserved.