[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-4-hydroxy-2-[[hydroxy(phosphonooxy)phosphoryl]oxymethyl]oxolan-3-yl] phosphono hydrogen phosphate

Base Information

• Chemical Name: [(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-4-hydroxy-2-[[hydroxy(phosphonooxy)phosphoryl]oxymethyl]oxolan-3-yl] phosphono hydrogen phosphate
• CAS No.: 32452-17-8
• Molecular Formula: C10H17N5O17P4
• Molecular Weight: 603.16
• Mol file: 32452-17-8.mol

Synonyms:

Chemical Property of [(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-4-hydroxy-2-[[hydroxy(phosphonooxy)phosphoryl]oxymethyl]oxolan-3-yl] phosphono hydrogen phosphate

Chemical Property:

• PKA: 1.38±0.10(Predicted)
• PSA: 402.84000
• Density: 2.85±0.1 g/cm3(Predicted)
• LogP: 0.75290
• XLogP3: -7.7
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 10
• Exact Mass: 602.95699208
• Heavy Atom Count: 36
• Complexity: 1090

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC2=C(N1C3C(C(C(O3)COP(=O)(O)OP(=O)(O)O)OP(=O)(O)OP(=O)(O)O)O)NC(=NC2=O)N
• Isomeric SMILES: C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)O)OP(=O)(O)OP(=O)(O)O)O)NC(=NC2=O)N

Technology Process of [(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-4-hydroxy-2-[[hydroxy(phosphonooxy)phosphoryl]oxymethyl]oxolan-3-yl] phosphono hydrogen phosphate

There total 6 articles about [(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-4-hydroxy-2-[[hydroxy(phosphonooxy)phosphoryl]oxymethyl]oxolan-3-yl] phosphono hydrogen phosphate 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: 25.0%

2'-O-(tert-butyldimethylsilyl)guanosine 3',5'-dipyrophosphate → guanosine 5'-diphosphate 3'-diphosphate (32452-17-8)

Guidance literature:

With water; acetic acid; for 6h; Time;

Reference yield:

2'-O-(tert-butyldimethylsilyl)guanosine 3',5'-diphosphate bis-triethylammonium salt → guanosine 5'-diphosphate 3'-diphosphate (32452-17-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; tributyl-amine; pyridine

1.2: 1 h / 20 °C

1.3: 0.5 h / 20 °C

2.1: palladium on activated carbon; hydrogen / methanol / 4 h / 20 °C

2.2: 1 h / 4 °C

2.3: 1 h / 20 °C

3.1: acetic acid; water / 6 h

With pyridine; tributyl-amine; palladium on activated carbon; water; hydrogen; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol;

Reference yield:

2'-O-(tert-butyldimethylsilyl)guanosine 3',5'-di(dibenzyl pyrophosphate) → guanosine 5'-diphosphate 3'-diphosphate (32452-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: palladium on activated carbon; hydrogen / methanol / 4 h / 20 °C

1.2: 1 h / 4 °C

1.3: 1 h / 20 °C

2.1: acetic acid; water / 6 h

With palladium on activated carbon; water; hydrogen; acetic acid; In methanol;

upstream raw materials:

2'-O-(tert-butyldimethylsilyl)-2-N-(dimethylaminomethylene)guanosine

Refernces

• 1、 Sato,Furuya. "Accumulation of guanosine polyphosphates by Brevibacterium ammoniagenes: isolation and identification of the products". . p. 465 - 474. Retrieved 2007/10/04.