O²,O^2'-anhydro-3-(3',5'-di-O-benzyl-β-D-arabinofuranosyl)-2,4-quinazolinedione

Base Information

• Chemical Name: O²,O^2'-anhydro-3-(3',5'-di-O-benzyl-β-D-arabinofuranosyl)-2,4-quinazolinedione
• CAS No.: 343921-87-9
• Molecular Formula: C₂₇H₂₄N₂O₅
• Molecular Weight: 456.498
• Mol file: 343921-87-9.mol

Synonyms:O²,O^2'-anhydro-3-(3',5'-di-O-benzyl-β-D-arabinofuranosyl)-2,4-quinazolinedione

Chemical Property of O²,O^2'-anhydro-3-(3',5'-di-O-benzyl-β-D-arabinofuranosyl)-2,4-quinazolinedione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O²,O^2'-anhydro-3-(3',5'-di-O-benzyl-β-D-arabinofuranosyl)-2,4-quinazolinedione

There total 3 articles about O²,O^2'-anhydro-3-(3',5'-di-O-benzyl-β-D-arabinofuranosyl)-2,4-quinazolinedione 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: 89.0%

anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) + 2-benzylthio-4,5-dihydro-(3',5'-di-O-benzyl-1',2'-dideoxy-β-D-arabinofuranoso)[1,2-d]-oxazole (343921-81-3) → O2,O2'-anhydro-3-(3',5'-di-O-benzyl-β-D-arabinofuranosyl)-2,4-quinazolinedione (343921-87-9)

Guidance literature:

With 3 A molecular sieve; camphor-10-sulfonic acid; In tert-butyl alcohol; Heating;

DOI:10.1016/j.tet.2004.01.032

Reference yield:

2-thiono-(1,2-dideoxy-β-D-arabinofurano)<1,2-d>oxazolidine (56270-92-9) → O2,O2'-anhydro-3-(3',5'-di-O-benzyl-β-D-arabinofuranosyl)-2,4-quinazolinedione (343921-87-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / NaH / dimethylformamide / 20 °C

2: 89 percent / molecular sieves 3 Angstroem; camphorsulfonic acid / 2-methyl-propan-2-ol / Heating

With 3 A molecular sieve; camphor-10-sulfonic acid; sodium hydride; In N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/j.tet.2004.01.032

Reference yield:

D-arabinofuranose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → O2,O2'-anhydro-3-(3',5'-di-O-benzyl-β-D-arabinofuranosyl)-2,4-quinazolinedione (343921-87-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / 37 percent HCl / H₂O / 20 - 55 °C

2: 0.695 g / NaH / dimethylformamide / 20 °C

3: 79 percent / molecular sieves 3 Angstroem / ethanol / 24 h / Heating

With hydrogenchloride; 3 A molecular sieve; sodium hydride; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)00357-4

upstream raw materials:

anthranilic acid

2-benzylthio-4,5-dihydro-(3',5'-di-O-benzyl-1',2'-dideoxy-β-D-arabinofuranoso)[1,2-d]-oxazole

2-thiono-(1,2-dideoxy-β-D-arabinofurano)<1,2-d>oxazolidine

D-arabinofuranose

Downstream raw materials:

3-(3',5'-di-O-benzyl-β-D-arabinosyl)-2,4-quinazolinedione

3-(3',5'-di-O-benzyl-β-D-ribosyl)-2,4-quinazolinedione

3-(3',5'-di-O-benzyl-2'-deoxy-β-D-ribofuranosyl)-2,4-quinazolinedione

3-(3',5'-di-O-benzyl-2'-O-phenoxythiocarbonyl-β-D-arabinosyl)-2,4-quinazolinedione