Acetic acid (2R,3S,4S,5R,6R,2'R,3'S,4'S,5'R,6'R)-4,5,3',4',5'-pentaacetoxy-6,6'-bis-acetoxymethyl-octahydro-[2,2']bipyranyl-3-yl ester | 190323-37-6

• 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: Acetic acid (2R,3S,4S,5R,6R,2'R,3'S,4'S,5'R,6'R)-4,5,3',4',5'-pentaacetoxy-6,6'-bis-acetoxymethyl-octahydro-[2,2']bipyranyl-3-yl ester
• 英文别名: [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxan-2-yl]methyl acetate
• CAS: 190323-37-6
• 化学式: C₂₈H₃₈O₁₈
• 分子量: 662.599
• InChiKey: VZAPLHIYWBTWMR-AXXYRMHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  229
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4S,5R,6R,2'R,3'S,4'S,5'R,6'R)-4,5,3',4',5'-pentaacetoxy-6,6'-bis-acetoxymethyl-octahydro-[2,2']bipyranyl-3-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以100%的产率得到1α-(α'-glucosyl)-1,5-anhydro-glucitol
  参考文献：
  名称：

  Synthesis and characterisation of hexa- and tetrasaccharide mimics from acetobromomaltotriose and acetobromomaltose, and of C-disaccharide mimics from acetobromoglucose, obtained by electrochemical reduction on silver

  摘要：

  Glucose-based glycomimetics characterised by a direct C-interglycosidic bond were synthesised from acetobromomaltotriose (ABMT), acetobromomaltose (ABM) and acetobromoglucose (ABG). Electroreduction on silver cathode of acetobromomaltotriose afforded the diastereoisomeric hexasaccharide mimics 1-3, which were deacetylated to 4-6. The same procedure afforded biglucosyl derivatives 10-12 from acetobromoglucose and tetrasaccharide mimics 15 and 16 from acetobromomaltose. The C-Br bond was reduced affording an intermediate anomeric radical whose coupling formed the new C-C bond. The electrochemical induced coupling resulted in a one-pot reaction to double the parent sugar units. NMR and molecular modelling were used for the conformational analysis of the diastereoisomers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.052
• 作为产物：
  描述：

  2-(Tetraacetyl-1-β-D-glucosylsulfonyl)-pyridin 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以20%的产率得到乙酰化葡萄烯糖
  参考文献：
  名称：

  在HMPA存在下，用碘化sa（II）对糖基2-吡啶基砜进行自由基二聚

  摘要：

  在HMPA存在下，通过碘化sa（II）还原糖基2-吡啶基砜可导致糖基二聚体的产率高达74％。这是通过自由基机制合理化的。

  DOI：

  10.1016/s0040-4039(98)00568-1

文献信息

• Reactivity of glucosyl radical in the presence of phenols
  作者：Angelo Alberti、Maria A. Della Bona、Dante Macciantelli、Francesca Pelizzoni、Guido Sello、Giangiacomo Torri、Elena Vismara

  DOI：10.1016/0040-4020(96)00558-3

  日期：1996.7

  Glucosyl radicals from the photoreaction of α-bromo-2,3,4,6-tetra-O-acetylglucose (ABG) with hexabutylditin react with phenols. 4-H3COC6H4O• was identified by means of EPR spectroscopy in the case of 4-methoxyphenol, and the corresponding α-O-glucoside was isolated along with 1- and 2-deoxysugars and the dimers of glucosyl radical. The present results are consistent with the formation of α-O-glucosides

  α-溴-2,3,4,6-四-O-乙酰葡萄糖（ABG）与六丁基二锡发生光反应的葡萄糖基与酚类发生反应。在4-甲氧基苯酚的情况下，通过EPR光谱法鉴定了4-H 3 COC 6 H 4 O•，并分离了相应的α - O-葡糖苷以及1-和2-脱氧糖以及葡糖基的二聚体。尽管在这种情况下，二聚体是主要反应产物，但本结果与在ABG和苯酚的电化学反应中观察到的α - O-葡萄糖苷的形成是一致的。