1,2,4,6-tetra-O-acetyl-3-O-dodecyl-β-D-glucopyranose | 125867-86-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,4,6-tetra-O-acetyl-3-O-dodecyl-β-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R,6S)-3,5,6-triacetyloxy-4-dodecoxyoxan-2-yl]methyl acetate
• CAS: 125867-86-9
• 化学式: C₂₆H₄₄O₁₀
• 分子量: 516.629
• InChiKey: JLILUHXAKRKMMK-WSGIOKLISA-N

物化性质

• 熔点：
  60-61 °C
• 沸点：
  558.5±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  36.0
• 可旋转键数：
  17.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,2,4,6-tetra-O-acetyl-3-O-dodecyl-β-D-glucopyranose 在 sodium metabisulfite 、 氢溴酸 作用下， 以 四氯化碳 、 溶剂黄146 、 丙酮 为溶剂， 反应 2.42h， 生成 2,4,6-tri-O-acetyl-3-O-dodecyl-1-thio-β-D-glucopyranose
  参考文献：
  名称：

  Organofluorine compounds and fluorinating agents

  摘要：

  Starting with 1,2,4,6-tetra-O-acetyl-3-O-dodecyl-beta-D-glucose (1), mixed alkyl-perfluoroalkyl substituted sugar derivatives with an anomeric perfluoroalkylthio group and an O-alkyl group in the 3 position were synthesized via 2,4,6-tri-O-acetyl-3-O-dodecyl-1-thio-beta-D-glucose (4). The latter was S-perfluorohexylated with 1-iodoperfluorohexane in a dithionite initiated reaction yielding perfluorohexyl 2,4,6-tri-O-acetyl-3-O-dodecyl-1-thio-beta-D-glucopyranoside (5). Experiments with the aim compound 5 completely to deacetylate ended in surprising results. Thus, methanolic methanolate solution produced the orthoester 7 as the result of a-fluoride replacement by methoxy groups as well as the methyl glucoside 8 as the result of a transglycosylation reaction. Alumina supported cesium fluoride cleaved regioselectively the two acetyl groups in the 4- and 6-position yielding perfluorohexyl 2-O-acetyl-3-O-dodecyl-1-thio-beta-D-glucopyranoside (10). A complete deacetylation of 5 to amphiphile 11 succeeded only with methanolic tert-butanolate. However, the products 8 and 10 were likewise formed. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2003.11.006
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-dodecyl-α-D-glucofuranose 在 硫酸 、 sodium acetate 作用下， 反应 5.0h， 生成 1,2,4,6-tetra-O-acetyl-3-O-dodecyl-β-D-glucopyranose
  参考文献：
  名称：

  Miethchen, Ralf; Holz, Jens; Peters, Dietmar, Zeitschrift fur Chemie, 1989, vol. 29, # 11, p. 420 - 421

  摘要：

  DOI：

文献信息

• Lipophilic sugar nucleotide synthesis by structure-based design of nucleotidylyltransferase substrates
  作者：Malcolm P. Huestis、Gaia A. Aish、Joseph P. M. Hui、Evelyn C. Soo、David L. Jakeman

  DOI：10.1039/b716955h

  日期：——

  Structure-based design of alkyl sugar-1-phosphates provides an efficient nucleotidylyltransferase-catalyzed synthesis of a series of new lipophilic sugar nucleotides possessing long or branched alkyl chains, thereby demonstrating the utility of nucleotidylyltransferases to catalyze the synthesis of sugar nucleotides with potential applications in lipopolysaccharide and lipoglycopeptide biosynthesis.

  基于结构的烷基糖-1-磷酸酯设计提供了一种高效的核苷酸转移酶催化合成一系列新型脂溶性糖核苷酸的方法，这些糖核苷酸具有较长或支链的烷基链，从而展示了核苷酸转移酶在催化合成具有潜在应用于脂多糖和脂糖肽生物合成的糖核苷酸方面的实用性。
• MIETHCHEN, RALF;KOLP, GUNDULA;PETERS, DIETMAR;HOLZ, JENS, Z. CHEM., 30,(1990) N, C. 56-57
  作者：MIETHCHEN, RALF、KOLP, GUNDULA、PETERS, DIETMAR、HOLZ, JENS

  DOI：——

  日期：——
• MIETHCHEN, RALF;HOL-, JENS;PETERS, DIETMAR, Z. CHEM., 29,(1989) N1, C. 420-421
  作者：MIETHCHEN, RALF、HOL-, JENS、PETERS, DIETMAR

  DOI：——

  日期：——
• MIETHCHEN, RALF;GABRIEL, TORSTEN;PETERS, DIETMAR;HOLZ, JENS;MICHALIK, MAN+, CARBOHYDR. RES., 214,(1991) N, C. 331-336
  作者：MIETHCHEN, RALF、GABRIEL, TORSTEN、PETERS, DIETMAR、HOLZ, JENS、MICHALIK, MAN+

  DOI：——

  日期：——