[(2R,3S)-2,4-diacetyloxy-3-hydroxy-3-methylbutyl] acetate | 77646-72-1

• 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: [(2R,3S)-2,4-diacetyloxy-3-hydroxy-3-methylbutyl] acetate
• CAS: 77646-72-1
• 化学式: C₁₁H₁₈O₇
• 分子量: 262.26
• InChiKey: BHJJQIKZXADFPL-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2R,3S)-2,4-diacetyloxy-3-hydroxy-3-methylbutyl] acetate 在 Amberlite IRA₄₀₀ 作用下， 生成 2-C-甲基-赤藓糖醇
  参考文献：
  名称：

  Stereochemistry of the Reduction Step Mediated by Recombinant 1-Deoxy-d-xylulose 5-Phosphate Isomeroreductase

  摘要：

  [GRAPHICS]The stereochemistry of the 1-deoxy-D-xylulose 5-phosphate (DXP) isomeroreductase reduction step has been examined using the recombinant enzyme from Synechocystis sp. PCC6803, Using [3-H-2]DXP and [4S-H-2]NADPH, it has been determined that the C1 pro-S hydrogen in the 2-C-methyl-D-erythritol 4-phosphate product derives from C3 of DXP, indicating that hydride attack occurs on the re face of the intermediate aldehyde, The 4S-hydride from NADPH is delivered, assigning this enzyme as a class B dehydrogenase.

  DOI：

  10.1021/ol990839n
• 作为产物：
  描述：

  (3aR,5R,6R,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol 在 palladium on activated charcoal sodium tetrahydroborate 、 sodium periodate 、 四丁基氟化铵 、 水 、 氢气 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 水 、 二甲基亚砜 、 异丙醇 为溶剂， -10.0~60.0 ℃ 、101.33 kPa 条件下， 反应 42.0h， 生成 [(2R,3S)-2,4-diacetyloxy-3-hydroxy-3-methylbutyl] acetate
  参考文献：
  名称：

  labeled标记的2 - C-甲基-d-赤藓糖醇的合成，这是阐明类异戊二烯生物合成的甲基赤藓糖醇磷酸途径的有用底物

  摘要：

  自由2- Ç甲基d赤藓糖醇被用于由异戊二烯生物合成大肠埃希氏杆菌缺少甲基赤磷酸途径，脱氧木酮糖磷酸合酶和isomero还原酶的两个第一酶突变体。为了进料实验，从容易获得的1,2 - O-异亚丙基-α-d-木呋喃糖中合成该四醇，总产率为43％，其中包括the标记的可能性。

  DOI：

  10.1016/s0040-4039(00)00726-7

文献信息

• Stereochemistry of the Reduction Step Mediated by Recombinant 1-Deoxy-<scp>d</scp>-xylulose 5-Phosphate Isomeroreductase
  作者：Philip J. Proteau、Youn-Hi Woo、R. Thomas Williamson、Chanokporn Phaosiri

  DOI：10.1021/ol990839n

  日期：1999.9.1

  [GRAPHICS]The stereochemistry of the 1-deoxy-D-xylulose 5-phosphate (DXP) isomeroreductase reduction step has been examined using the recombinant enzyme from Synechocystis sp. PCC6803, Using [3-H-2]DXP and [4S-H-2]NADPH, it has been determined that the C1 pro-S hydrogen in the 2-C-methyl-D-erythritol 4-phosphate product derives from C3 of DXP, indicating that hydride attack occurs on the re face of the intermediate aldehyde, The 4S-hydride from NADPH is delivered, assigning this enzyme as a class B dehydrogenase.
• Synthesis of tritium labelled 2-C-methyl-d-erythritol, a useful substrate for the elucidation of the methylerythritol phosphate pathway for isoprenoid biosynthesis
  作者：Jean-François Hoeffler、Catherine Grosdemange-Billiard、Michel Rohmer

  DOI：10.1016/s0040-4039(00)00726-7

  日期：2000.6

  Free 2-C-methyl-d-erythritol is utilised for isoprenoid biosynthesis by Escherichiacoli mutants lacking the two first enzymes of the methylerythritol phosphate pathway, the deoxyxylulose phosphate synthase and isomero-reductase. For feeding experiments, this tetrol was synthesised with an overall 43% yield from readily available 1,2-O-isopropylidene-α-d-xylofuranose, including the possibility of tritium

  自由2- Ç甲基d赤藓糖醇被用于由异戊二烯生物合成大肠埃希氏杆菌缺少甲基赤磷酸途径，脱氧木酮糖磷酸合酶和isomero还原酶的两个第一酶突变体。为了进料实验，从容易获得的1,2 - O-异亚丙基-α-d-木呋喃糖中合成该四醇，总产率为43％，其中包括the标记的可能性。