(2R,3R)-4-<(triisopropylsilyl)oxy>-2,3-(isopropylidenedioxy)butanal | 221154-53-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-4-<(triisopropylsilyl)oxy>-2,3-(isopropylidenedioxy)butanal
• 英文别名: (2R,3R)-4-[(triisopropylsilyl)oxy]-2,3-(isopropylidenedioxy)butanal
• CAS: 221154-53-6
• 化学式: C₁₆H₃₂O₄Si
• 分子量: 316.513
• InChiKey: VHNSMELBNYXNAK-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-4-<(triisopropylsilyl)oxy>-2,3-(isopropylidenedioxy)butanal 在 2,6-二甲基吡啶 、 N-甲基吡咯烷酮 、 四丙基高钌酸铵 、 4 Angstroems MS 、 四丁基氟化铵 、 四氯化碲 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 11.5h， 生成 dimethyl (3S,4R)-3,4-isopropylidenedioxy-2-(1,3-dioxolane)-5-oxopentyl phosphate
  参考文献：
  名称：

  Synthesis of 1-Deoxy-d-xylulose and 1-Deoxy-d-xylulose-5-phosphate

  摘要：

  1-Deoxy-D-xylulose (4) and the corresponding 5-phosphate (5) are substrates for the first pathway-specific enzymes in the biosynthesis of thiamine diphosphate (vitamin B-1), pyridoxol phosphate (vitamin B-6), and the nonmevalonate family of isoprenoid compounds recently discovered in bacteria and plant chloroplasts. Both 4 and 5 were synthesized from commercially available (-)-2,3-O-isopropylidene-D-threitol (10). The protected tetraol was converted to (-)-3,4-O-isopropylidene-5-triisopropylsilyl-1-deoxy-D-xylulose (14) in four steps. Treatment of 14 with acetic acid gave 4 in an overall yield of 69%. The corresponding 5-phosphate was obtained by protection the carbonyl group in 14, removal of the triisopropylsilyl moiety, and treatment of the resulting alcohol with trimethyl phosphite/TeCl4, trimethylsilyl bromide, water, and HCl in successive steps to give 5 in 58% overall yield from 10.

  DOI：

  10.1021/jo981966k
• 作为产物：
  描述：

  三异丙基氯硅烷 在 草酰氯 、 sodium hydride 、 二甲基亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,3R)-4-<(triisopropylsilyl)oxy>-2,3-(isopropylidenedioxy)butanal
  参考文献：
  名称：

  用于研究脱氧木酮糖5-磷酸还原异构酶抑制作用的底物类似物：合成和评估。

  摘要：

  合成了5-磷酸脱氧木酮糖（DXP）类似物，并评估了重组拟南芥PCC6803 DXP还原异构酶（DXR; EC 1.1.1.267）的替代底物和抑制剂。测试的化合物中的五种（1,2-二脱氧-D-苏--3-己糖6-磷酸酯，1-脱氧-1-核糖5-磷酸酯，2S，3R-二羟基丁酰胺4-磷酸酯，4S-羟基戊烷-2-酮与磷霉素相比，5-磷酸和3S-羟基戊-2--2-酮（5-磷酸）起相对较弱的竞争性抑制剂的作用。第六种化合物3R，4S-二羟基-5-氧己基膦酸用作替代底物，最近有报道称该化合物与大肠杆菌DXR相同。

  DOI：

  10.1016/j.bmcl.2004.08.023

文献信息

• Synthesis and Evaluation of 1-Deoxy-<scp>d</scp>-xylulose 5-Phosphoric Acid Analogues as Alternate Substrates for Methylerythritol Phosphate Synthase
  作者：David T. Fox、C. Dale Poulter

  DOI：10.1021/jo048022h

  日期：2005.3.1

  [GRAPHICS]Four deoxyxylulose phosphate (DXP) analogues were synthesized and evaluated as substrates/ inhibitors for methylerythritol phosphate (MEP) synthase. In analogues CF3-DXP (1), CF2-DXP (2), and CF-DXP (3), the three methyl hydrogens at Cl of DXP were sequentially replaced by fluorine. In the fourth analogue, Et-DXP (4), the methyl group in DXP was replaced by an ethyl moiety. Analogues 1, 2, and 4 were not substrates for MEP synthase under normal catalytic conditions and were instead modest inhibitors with IC50 values of 2.0, 3.4, and 6.2 mM, respectively. In contrast, 3 was a good substrate (k(cat) = 38 s(-1), K-m = 227 mu M) with a turnover rate similar to that of the natural substrate. These results are consistent with a retro-aldol/aldol mechanism rather than an a-ketol rearrangement for the enzyme-catalyzed conversion of DXP to MEP.