(4S)-4-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2,2-dimethyl-1,3-dioxan-5-one | 148839-58-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S)-4-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2,2-dimethyl-1,3-dioxan-5-one
• CAS: 148839-58-1
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: ZTRJKTLXNSXAIA-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-4-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2,2-dimethyl-1,3-dioxan-5-one 在 acid resin Dowex 作用下， 以 水 为溶剂， 反应 1.0h， 生成 4-deoxy-D-fructose
  参考文献：
  名称：

  Syntheses of 4-deoxy-d-fructose and enzymatic affinity study

  摘要：

  Enantiomerically pure 4-deoxy-D-fructose has been prepared and characterised in a protected form, acidic hydrolysis of which led to an aqueous solution of 4-deoxy-D-fructose. Activities of this compound with enzymes of the glycolysis pathway involved in glucose metabolism make possible access to 4-deoxy-D-fructose-6-phosphate, 4-deoxy-D-glucose-6-phosphate and 4-deoxy-D-gluconate-6-phosphate. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00398-x
• 作为产物：
  描述：

  (R)-(-)-对甲基苯磺酸-2,2-二甲基-1,3-二氧戊环基-4-甲酯 在 正丁基锂 、 臭氧 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.5h， 生成 (4S)-4-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2,2-dimethyl-1,3-dioxan-5-one
  参考文献：
  名称：

  Syntheses of 4-deoxy-d-fructose and enzymatic affinity study

  摘要：

  Enantiomerically pure 4-deoxy-D-fructose has been prepared and characterised in a protected form, acidic hydrolysis of which led to an aqueous solution of 4-deoxy-D-fructose. Activities of this compound with enzymes of the glycolysis pathway involved in glucose metabolism make possible access to 4-deoxy-D-fructose-6-phosphate, 4-deoxy-D-glucose-6-phosphate and 4-deoxy-D-gluconate-6-phosphate. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00398-x

文献信息

• Preparation and Reactions of 2,2-Dimethyl-1,3-dioxan-5-one-SAMP-Hydrazone: A Versatile Chiral Dihydroxyacetone Equivalent
  作者：Dieter Enders、Matthias Voith、Stuart J. Ince

  DOI：10.1055/s-2002-33646

  日期：——

  The SAMP-hydrazone of 2,2-dimethyl-1,3-dioxan-5-one represents a valuable chiral dihydroxyacetone equivalent. Asymmetric mono- or α,α′-bisalkylations followed by auxiliary cleavage leads to the corresponding mono- or α,α′-disubstituted, acetonide protected ketodiols in excellent diastereo- and enantiomeric excesses.

  2,2-二甲基-1,3-二恶烷-5-酮的SAMP-脒代表了有价值的手性二羟基丙酮等效物。通过不对称单烷基化或α,α'-双烷基化，随后辅助断裂，可以高对映选择性和立体选择性地得到相应的单或α,α'-双取代、乙缩醛保护的酮二醇。
• 1,3-Dioxan-5-one as C3-building block for the diastereo- and enantioselective synthesis of C5- to C9-deoxy sugars using the SAMP-/RAMP-hydrazone method
  作者：D. Enders、U. Jegelka

  DOI：10.1016/s0040-4039(00)60439-2

  日期：1993.4

  The diastereo- and enantioselective synthesis of deoxy- and, dideoxysugars is demonstrated using the protected dihydroxyacetone derivative 8 as a C3-building block in combination with the SAMP-/RAMP-hydrazone method.
• Syntheses of 4-deoxy-d-fructose and enzymatic affinity study
  作者：Corinne André、Jean Bolte、Colette Demuynck

  DOI：10.1016/s0957-4166(98)00398-x

  日期：1998.11

  Enantiomerically pure 4-deoxy-D-fructose has been prepared and characterised in a protected form, acidic hydrolysis of which led to an aqueous solution of 4-deoxy-D-fructose. Activities of this compound with enzymes of the glycolysis pathway involved in glucose metabolism make possible access to 4-deoxy-D-fructose-6-phosphate, 4-deoxy-D-glucose-6-phosphate and 4-deoxy-D-gluconate-6-phosphate. (C) 1998 Elsevier Science Ltd. All rights reserved.