(4R,5R)-(2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)methanol | 221154-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-(2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)methanol
• 英文别名: (2R,3R)-4-<(triisopropylsilyl)oxy>-2,3-(isopropylidenedioxy)butanol；[(4R,5R)-2,2-dimethyl-5-[tri(propan-2-yl)silyloxymethyl]-1,3-dioxolan-4-yl]methanol
• CAS: 221154-50-3
• 化学式: C₁₆H₃₄O₄Si
• 分子量: 318.529
• InChiKey: YBJGPRBLTPGEHI-HUUCEWRRSA-N

物化性质

• 沸点：
  366.9±27.0 °C(Predicted)
• 密度：
  0.935±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R)-(2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)methanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.25h， 生成 (3S,4R)-5-<(triisopropylsilyl)oxy>-3,4-(isopropylidenedioxy)pentan-2-ol
  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 、 (-)-2,3-O-亚异丙基-D-苏力糖醇 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到(4R,5R)-(2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)methanol
  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

• Substrate analogs for the investigation of deoxyxylulose 5-phosphate reductoisomerase inhibition: synthesis and evaluation
  作者：Chanokporn Phaosiri、Philip J. Proteau

  DOI：10.1016/j.bmcl.2004.08.023

  日期：2004.11

  Deoxyxylulose 5-phosphate (DXP) analogs were synthesized and evaluated as alternative substrates and inhibitors of recombinant Synechocystis PCC6803 DXP reductoisomerase (DXR; EC 1.1.1.267). Five of the compounds tested (1,2-dideoxy-D-threo-3-hexulose 6-phosphate, 1-deoxy-l-ribulose 5-phosphate, 2S,3R-dihydroxybutyramide 4-phosphate, 4S-hydroxypentan-2-one 5-phosphate, and 3S-hydroxypentan-2-one 5-phosphate)

  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。
• 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.
• Synthesis of 1-Deoxy-<scp>d</scp>-xylulose and 1-Deoxy-<scp>d</scp>-xylulose-5-phosphate
  作者：Brian S. J. Blagg、C. Dale Poulter

  DOI：10.1021/jo981966k

  日期：1999.3.1

  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.
• Synthesis and Evaluation of 1-Deoxy-<scp>d</scp>-xylulose 5-Phosphate Analogues as Chelation-Based Inhibitors of Methylerythritol Phosphate Synthase
  作者：Joel R. Walker、C. Dale Poulter

  DOI：10.1021/jo0516786

  日期：2005.11.1

  A series of 1-deoxy-D-xylulose 5-phosphate (DXP) analogues were synthesized and evaluated as inhibitors of E. coli methylerythritol phosphate (MEP) synthase. In analogues 1-4, the methyl group in DXP was replaced by hydroxyl, hydroxylamino, methoxy, and amino moieties, respectively. In analogues 5 and 6, the acetyl moiety in DXP was replaced by hydroxymethyl and aminomethyl groups. These compounds were designed to coordinate to the active site divalent metal in MEP synthase. The carboxylate (1), methyl ester (3), amide (4), and alcohol (5) analogues were inhibitors with IC50's ranging from 0.25 to 1.0 mM. The hydroxamic acid (2) and amino (6) analogues did not inhibit the enzyme.