(Z)-1-(5-azido-2,5-dideoxy-3-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl)-5-(phenylmethylene)-2,4-imidazolidinedione

Base Information

• Chemical Name: (Z)-1-(5-azido-2,5-dideoxy-3-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl)-5-(phenylmethylene)-2,4-imidazolidinedione
• CAS No.: 156270-80-3
• Molecular Formula: C₂₃H₂₁N₅O₅
• Molecular Weight: 447.45
• Mol file: 156270-80-3.mol

Synonyms:(Z)-1-(5-azido-2,5-dideoxy-3-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl)-5-(phenylmethylene)-2,4-imidazolidinedione

Chemical Property of (Z)-1-(5-azido-2,5-dideoxy-3-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl)-5-(phenylmethylene)-2,4-imidazolidinedione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-1-(5-azido-2,5-dideoxy-3-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl)-5-(phenylmethylene)-2,4-imidazolidinedione

There total 4 articles about (Z)-1-(5-azido-2,5-dideoxy-3-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl)-5-(phenylmethylene)-2,4-imidazolidinedione 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:

4-methyl-benzoyl chloride (874-60-2) → (Z)-1-(5-azido-2,5-dideoxy-3-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl)-5-(phenylmethylene)-2,4-imidazolidinedione (156270-80-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / pyridine / 16 h / Ambient temperature

2: 1.) (NH₄)2SO₄, 1,1,1,3,3,3-hexamethyldisilazane, 2.) trimethylsilyl trifluoromethanesulfonate / 1.) reflux, 2.) MeCN, -50 - -30 deg C

With ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane; In pyridine;

DOI:10.1080/15257779408013274

Reference yield:

2′-deoxy-1′-O-methyl-5′-azido-D-ribofuranose (170553-85-2) → (Z)-1-(5-azido-2,5-dideoxy-3-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl)-5-(phenylmethylene)-2,4-imidazolidinedione (156270-80-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / pyridine / 16 h / Ambient temperature

2: 1.) (NH₄)2SO₄, 1,1,1,3,3,3-hexamethyldisilazane, 2.) trimethylsilyl trifluoromethanesulfonate / 1.) reflux, 2.) MeCN, -50 - -30 deg C

With ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane; In pyridine;

DOI:10.1080/15257779408013274

Reference yield:

1-O-methyl-2-deoxy-D-ribofuranoside (51255-17-5,51255-18-6,60134-26-1,89577-26-4,96038-80-1,96039-31-5,144301-84-8,144301-85-9) → (Z)-1-(5-azido-2,5-dideoxy-3-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl)-5-(phenylmethylene)-2,4-imidazolidinedione (156270-80-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 51 percent / triphenyl phosphine, NaN₃, CBr₄ / dimethylformamide / 168 h / Ambient temperature

2: 40 percent / pyridine / 16 h / Ambient temperature

3: 1.) (NH₄)2SO₄, 1,1,1,3,3,3-hexamethyldisilazane, 2.) trimethylsilyl trifluoromethanesulfonate / 1.) reflux, 2.) MeCN, -50 - -30 deg C

With ammonium sulfate; sodium azide; carbon tetrabromide; trimethylsilyl trifluoromethanesulfonate; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; In pyridine; N,N-dimethyl-formamide;

DOI:10.1080/15257779408013274

upstream raw materials:

methyl 5-azido-2,5-dideoxy-3-O-(4-methylbenzoyl)-α-D-erythro-pentofuranoside

5-benzylidenehydantoin

4-methyl-benzoyl chloride

2′-deoxy-1′-O-methyl-5′-azido-D-ribofuranose

Downstream raw materials:

(Z)-1-(5-azido-2,5-dideoxy-β-D-erythro-pentofuranosyl)-5-(phenylmethylene)-2,4-imidazolidinedione