(2E)-4-hydroxy-3-methylbut-2-en-1-yl trihydrogen diphosphate

Base Information

• Chemical Name: (2E)-4-hydroxy-3-methylbut-2-en-1-yl trihydrogen diphosphate
• CAS No.: 396726-03-7
• Molecular Formula: C5H12O8P2
• Molecular Weight: 262.093
• ChEMBL ID: CHEMBL145233
• DSSTox Substance ID: DTXSID60649459
• Metabolomics Workbench ID: 28000
• Nikkaji Number: J1.892.495A,J1.669.907A
• Pharos Ligand ID: MFQ3XXRKZ456
• Wikidata: Q76285996
• Mol file: 396726-03-7.mol

Synonyms:(E)-4-hydroxy-3-methylbut-2-enyl diphosphate;4-HMDP cpd

Chemical Property of (2E)-4-hydroxy-3-methylbut-2-en-1-yl trihydrogen diphosphate

Chemical Property:

• PSA: 161.63000
• LogP: 1.46590
• Storage Temp.: ?20°C
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 262.00074133
• Heavy Atom Count: 15
• Complexity: 317

Purity/Quality:

99% ^*data from raw suppliers

1-Hydroxy-2-methyl-2-buten-4-yl4-Diphosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCOP(=O)(O)OP(=O)(O)O)CO
• Isomeric SMILES: C/C(=C\COP(=O)(O)OP(=O)(O)O)/CO
• Uses: 1-Hydroxy-2-methyl-2-buten-4-yl 4-Diphosphate is an isoprenoid precursor produced by Plasmodium falciparum that affects A. gambiae s.l. blood meal seeking and feeding behaviours as well as susceptibility to infection.

Technology Process of (2E)-4-hydroxy-3-methylbut-2-en-1-yl trihydrogen diphosphate

There total 6 articles about (2E)-4-hydroxy-3-methylbut-2-en-1-yl trihydrogen diphosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

trans-3-hydroxymethyl-2-butenyl chloride (56904-88-2) → (E)-(4-hydroxy-3-methylbut-2-enyl)phosphonophosphoric acid (396726-03-7)

Guidance literature:

trans-3-hydroxymethyl-2-butenyl chloride; With tris(tetra-n-butylammonium) hydrogen pyrophosphate; In acetonitrile; at 20 ℃; for 2h;

With DOWEX 50WX₈-200; ammonium bicarbonate; In isopropyl alcohol; pH=8.0; Further stages.;

DOI:10.1021/jo0258453

Reference yield:

2-hydroxy-2-methyl-3-butenal dimethyl acetal (3330-23-2) → (E)-(4-hydroxy-3-methylbut-2-enyl)phosphonophosphoric acid (396726-03-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 164 mg / NaCl; conc. HCl / CuCl₂ / benzene / 0 - 50 °C

2.1: 80 percent / NaBH₄ / tetrahydrofuran / 5 h / -20 °C

3.1: tris(tetra-n-butylammonium) hydrogen pyrophosphate / acetonitrile / 2 h / 20 °C

3.2: 83 percent / Dowex 50WX₈-200; NH₄HCO₃ / propan-2-ol / pH 8.0

With hydrogenchloride; sodium tetrahydroborate; tris(tetra-n-butylammonium) hydrogen pyrophosphate; sodium chloride; copper dichloride; In tetrahydrofuran; acetonitrile; benzene;

DOI:10.1021/jo0258453

Reference yield:

2C-methyl-D-erythritol 2,4-O-cyclodiphosphate (151435-51-7,141816-32-2) → (E)-(4-hydroxy-3-methylbut-2-enyl)phosphonophosphoric acid (396726-03-7)

Guidance literature:

With Escherichia coli; gcpE genes; In water; at 37 ℃; for 20h;

DOI:10.1016/S0040-4039(02)00003-5

upstream raw materials:

2C-methyl-D-erythritol 2,4-O-cyclodiphosphate

trans-3-hydroxymethyl-2-butenyl chloride

((E)-4-bromo-2-methylbut-2-en-1-ol)

(E)-4-chloro-2-methylbut-2-enal

Downstream raw materials:

dimethylallyl diphosphate

isopentyl pyrophosphate

(E)-1,4-diacetoxy-2-methyl-2-butene

Refernces

• 1、 Reichenberg, Armin,Hintz, Martin,Kletschek, Yvonne,Kuhl, Tanja,Haug, Christian,Engel, Rosel,Moll, Jens,Ostrovsky, Dmitry N.,Jomaa, Hassan,Eberl, Matthias. "Replacing the pyrophosphate group of HMB-PP by a diphosphonate function abrogates its potential to activate human γδ T cells but does not lead to competitive antagonism". . p. 1257 - 1260. Retrieved 2003.
• 2、 Seemann, Myriam,Campos, Narciso,Rodriguez-Concepción, Manuel,Iba?ez, Ester,Duvold, Tore,Tritsch, Denis,Boronat, Albert,Rohmer, Michel. "Isoprenoid biosynthesis in Escherichia coli via the methylerythritol phosphate pathway: Enzymatic conversion of methylerythritol cyclodiphosphate into a phosphorylated derivative of (E)-2-methylbut-2-ene-1,4-diol". . p. 1413 - 1415. Retrieved 2007/10/03.