(8R)-3-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepin-8-ol

Base Information

• Chemical Name: (8R)-3-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepin-8-ol
• CAS No.: 82228-59-9
• Molecular Formula: C₂₅H₂₈N₄O₄
• Molecular Weight: 448.522
• Mol file: 82228-59-9.mol

Synonyms:(8R)-3-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepin-8-ol

Chemical Property of (8R)-3-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepin-8-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8R)-3-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepin-8-ol

There total 7 articles about (8R)-3-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepin-8-ol 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:

3-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6,7-dihydroimidazo<4,5-d><1,3>diazepin-8(3H)-one (69196-01-6) → (8R)-3-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepin-8-ol (82228-59-9) + (8S)-3-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepin-8-ol (82228-60-2)

Guidance literature:

With hydrogen; nickel; In tetrahydrofuran; methanol; at 5 - 25 ℃; for 17h; under 760 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00139a015

Reference yield:

2-deoxy-3,5-di-O-(p-toluoyl)-D-erythro-pentofuranosyl chloride (52162-55-7) → (8R)-3-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepin-8-ol (82228-59-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) N,N-bis(trimethylsilyl)trifluoroacetamide, pyridine, 2.) SnCl₄ / 1.) CH₃CN, room temperature, overnight, 2.) CH₃CN, 1,2-dichloroethane, -45 deg C to -35 deg C, 0.75 h

2: H₂ / Raney Nickel / acetone; methanol / 17 h / 5 - 25 °C / 760 Torr

With pyridine; 2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide; hydrogen; tin(IV) chloride; nickel; In methanol; acetone;

DOI:10.1021/jo00139a015

Reference yield:

2-amino-1-(5-amino-1H-imidazol-4-yl)ethanone dihydrochloride (69195-92-2) → (8R)-3-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepin-8-ol (82228-59-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / 0.25 h / 65 °C

2: 1.) N,N-bis(trimethylsilyl)trifluoroacetamide, pyridine, 2.) SnCl₄ / 1.) CH₃CN, room temperature, overnight, 2.) CH₃CN, 1,2-dichloroethane, -45 deg C to -35 deg C, 0.75 h

3: H₂ / Raney Nickel / acetone; methanol / 17 h / 5 - 25 °C / 760 Torr

With pyridine; 2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide; hydrogen; tin(IV) chloride; nickel; In methanol; acetone;

DOI:10.1021/jo00139a015

upstream raw materials:

3-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6,7-dihydroimidazo<4,5-d><1,3>diazepin-8(3H)-one

2-deoxy-3,5-di-O-(p-toluoyl)-D-erythro-pentofuranosyl chloride

2-amino-1-(5-amino-1H-imidazol-4-yl)ethanone dihydrochloride

2-amino-1-[5-amino-1-(phenylmethyl)-1H-imidazol-4-yl]ethanone dihydrochloride