O²,O³,O⁵,O⁶-tetraacetyl-L-galactonic acid-lactone | 210100-08-6

• 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: O²,O³,O⁵,O⁶-tetraacetyl-L-galactonic acid-lactone
• 英文别名: O²,O³,O⁵,O⁶-Tetraacetyl-L-galactonsaeure-lacton；[(2S)-2-acetyloxy-2-[(2R,3R,4S)-3,4-diacetyloxy-5-oxooxolan-2-yl]ethyl] acetate
• CAS: 210100-08-6
• 化学式: C₁₄H₁₈O₁₀
• 分子量: 346.291
• InChiKey: DDWMFFZVZXMXCS-LOWDOPEQSA-N

物化性质

• 沸点：
  383.3±42.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  O²,O³,O⁵,O⁶-tetraacetyl-L-galactonic acid-lactone 在 palladium on activated charcoal 盐酸 、 六甲基磷酰三胺 、 samarium diiodide 、 氢气 、 二正丁基氧化锡 、 三乙胺 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙二醇 、 乙酸乙酯 为溶剂， 反应 56.0h， 生成 (5S)-5-[(1S)-2-benzyloxy-1-hydroxyethyl]tetrahydrofuran-2-one
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol. 13. Protein Kinase C Ligands Based on Templates Derived from 2,3-Dideoxy-l-erythro(threo)-hexono-1,4-lactone and 2-Deoxyapiolactone

  摘要：

  In the present investigation, the last two possible modes of generating conformationally semirigid diacylglycerol (DAG) analogues embedded into five-membered ring lactones as templates III and IV are investigated. The first two templates studied in previous investigations corresponded to 2-deoxyribonolactone (template I) and 4,4-disubstituted gamma-butyrolactone (template II), with the latter producing potent protein kinase C (PK-C) ligands with low nanomolar binding affinities. The templates reported in this work correspond to 2,3-dideoxy-L-erythro- or -threo-hexono-1,4-lactone (template III) and 2-deoxyapiolactone (template IV). Compounds constructed with the dideoxy-L-erythro- or -threo-hexono-1,4-lactone template were synthesized stereospecifically from tri-O-acetyl-L-glucal and L-galactono-1,4-lactone, respectively. Compounds constructed with the 2-deoxyapiolactone template were synthesized stereoselectively from di-O-isopropylidene-alpha-D-apiose. Inhibition of the binding of [H-3]phorbol-12,13-dibutyrate to PK-C alpha showed that only the threo-isomer, 5-O-tetradecanoyl-2,3-dideoxy-L-threo-hexono-1,4-lactone (2) was a good PK-C ligand (K-i = 1 mu M). The rest of the ligands had poorer affinities with K-i values between 10 and 28 mu M. With these results, the order of importance of five-membered ring lactones as competent templates for the construction of semirigid DAG surrogates with effective PK-C binding affinity can be established as II much greater than I similar to III > IV.

  DOI：

  10.1021/jm960525v
• 作为产物：
  描述：

  乙酸酐 、 半乳糖酸內酯 在 吡啶 作用下， 生成 O²,O³,O⁵,O⁶-tetraacetyl-L-galactonic acid-lactone
  参考文献：
  名称：

  Synthesis of Perseulose (L-Galaheptulose)

  摘要：

  DOI：

  10.1021/ja01175a030

文献信息

• Chemical synthesis of GDP-l-galactose and analogues
  作者：Hayley Binch、Katja Stangier、Joachim Thiem

  DOI：10.1016/s0008-6215(97)10094-5

  日期：1998.1

  Succinct syntheses for L-galactose, 3-deoxy-L-xylo-hexose (3-deoxy-L-galactose), 6-deoxy-L-galactopyranose (L-fucose) and 3,6-dideoxy-L-xylo-hexose (3,6-dideoxy-L-galactose) have been developed starting from commercially available L-galactono-1,4-lactone. L-Galactose and variants were then converted to the guanosine diphosphate derivatives, via the formation of the anomeric phosphates and coupling to guanosine monophosphate morpholidate. (C) 1998 Elsevier Science Ltd. All rights reserved.