n-Glycyl-5-o-phosphonopentofuranosylamine

Base Information

• Chemical Name: n-Glycyl-5-o-phosphonopentofuranosylamine
• CAS No.: 92379-77-6
• Molecular Formula: C₇H₁₅N₂O₈P
• Molecular Weight: 286.178
• NSC Number: 333308
• DSSTox Substance ID: DTXSID80864203
• Wikidata: Q110078106
• Mol file: 92379-77-6.mol

Synonyms:92379-77-6;N-(Aminoacetyl)-5-O-phosphonopentofuranosylamine;NSC 333308;NSC333308;n-glycyl-5-o-phosphonopentofuranosylamine;DTXSID80864203;NSC-333308;[5-[(2-aminoacetyl)amino]-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate;[5-[(2-Aminoacetyl)amino]-3,4-dihydroxyoxolan-2-yl]methyl dihydrogenphosphate

Chemical Property of n-Glycyl-5-o-phosphonopentofuranosylamine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 181.38000
• Density: 1.72g/cm³
• LogP: -2.29150
• XLogP3: -6.8
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 286.05660244
• Heavy Atom Count: 18
• Complexity: 346

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(O1)NC(=O)CN)O)O)OP(=O)(O)O

Technology Process of n-Glycyl-5-o-phosphonopentofuranosylamine

There total 7 articles about n-Glycyl-5-o-phosphonopentofuranosylamine 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: 65.0%

2,3-O-isopropylidene-D-ribofuranosylamine-5-phosphate → glycinamide ribonucleotide (92379-77-6)

Guidance literature:

With trifluoroacetic acid;

DOI:10.3987/COM-18-S(T)50

Reference yield: 60.0%

2,3-O-isopropylidene-D-ribofuranosylamine-5-phosphate (124575-23-1) → glycinamide ribonucleotide (92379-77-6)

Guidance literature:

With trifluoroacetic acid; In water; at 20 ℃; for 5h;

DOI:10.3987/COM-18-S(T)50

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → glycinamide ribonucleotide (92379-77-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / TMSN₃ / SnCl₄ / CH₂Cl₂

2: 1.) H₂; 2.) DCC / 1.) PtO₂ / 1.) acetone

3: 2.) Dowex 50W-X₈ / 1.) NaOMe / 1.) MeOH

4: Dowex 50W-X₈ / acetone

5: 1.) 1H-tetrazole; 2.) m-CPBA / 1.) CH₂Cl₂

6: 64 percent / H₂ / Pd-C / aq. ethanol

7: TFA / H₂O / 24 h / Ambient temperature

With 1H-tetrazole; trimethylsilylazide; Dowex 50W-X₈; hydrogen; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; platinum(IV) oxide; palladium on activated charcoal; sodium methylate; tin(IV) chloride; In ethanol; dichloromethane; water; acetone;

DOI:10.1016/S0040-4039(00)99530-3

upstream raw materials:

2,3-O-isopropylidene-D-ribofuranosylamine-5-phosphate

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

N-(N-benzyloxycarbonyl-glycyl)-α-D-ribofuranosylamine

[((3aR,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylcarbamoyl)-methyl]-carbamic acid benzyl ester