2C-Methyl-D-erythritol 2,4-cyclodiphosphate

Base Information

• Chemical Name: 2C-Methyl-D-erythritol 2,4-cyclodiphosphate
• CAS No.: 151435-51-7
• Molecular Formula: C5H12O9P2
• Molecular Weight: 278.092
• DSSTox Substance ID: DTXSID501123383
• Nikkaji Number: J726.915C,J1.317.663I
• Wikidata: Q27103069
• Metabolomics Workbench ID: 51273
• Mol file: 151435-51-7.mol

Synonyms:3-methyl-1,2,3,4-tetrahydroxybutane-1,3-cyclic bisphosphate;3-MTHBCP

Chemical Property of 2C-Methyl-D-erythritol 2,4-cyclodiphosphate

Chemical Property:

• Boiling Point: 483.1±55.0 °C(Predicted)
• PKA: 0.93±0.60(Predicted)
• PSA: 162.37000
• Density: 1.79±0.1 g/cm3(Predicted)
• LogP: -0.63750
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 1
• Exact Mass: 277.99565595
• Heavy Atom Count: 16
• Complexity: 356

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(COP(=O)(OP(=O)(O1)O)O)O)CO
• Isomeric SMILES: C[C@@]1([C@@H](COP(=O)(OP(=O)(O1)O)O)O)CO

Technology Process of 2C-Methyl-D-erythritol 2,4-cyclodiphosphate

There total 2 articles about 2C-Methyl-D-erythritol 2,4-cyclodiphosphate 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:

2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol → cytidine monophosphate (63-37-6,30811-80-4) + 2C-methyl-D-erythritol 2,4-O-cyclodiphosphate (151435-51-7,141816-32-2)

Guidance literature:

With 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase; magnesium chloride; In various solvent(s); at 37 ℃; for 2h; pH=8.0;

DOI:10.1016/S0040-4039(00)00375-0

Reference yield:

(2R,3R)-4-hydorxy-3-methyl-2,3-epoxybutanyl diphosphate (1196056-86-6) → 2C-methyl-D-erythritol 2,4-O-cyclodiphosphate (151435-51-7,141816-32-2)

Guidance literature:

With IspG enzyme; at 37 ℃; pH=8; aq. buffer; Inert atmosphere; Enzymatic reaction;

DOI:10.1039/c0cc02594a

Reference yield:

2C-methyl-D-erythritol 2,4-O-cyclodiphosphate (151435-51-7,141816-32-2) → (E)-1,4-diacetoxy-2-methyl-2-butene (59054-99-8,30264-54-1)

Guidance literature:

Multi-step reaction with 3 steps

1: Escherichia coli; yfgA, yfgB, gcpE genes / H₂O / 20 h / 37 °C

2: Escherichia coli Type III S alkaline phosphatase / H₂O

3: pyridine / 20 °C

With pyridine; Escherichia coli; Escherichia coli Type III S alkaline phosphatase; gcpE genes; In water;

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

upstream raw materials:

(2R,3R)-4-hydorxy-3-methyl-2,3-epoxybutanyl diphosphate

Downstream raw materials:

(E)-(4-hydroxy-3-methylbut-2-enyl)phosphonophosphoric acid

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