4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate

Base Information

• Chemical Name: 4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate
• CAS No.: 198008-12-7
• Molecular Formula: C₂₄H₂₃N₅O₅
• Molecular Weight: 461.477
• Mol file: 198008-12-7.mol

Synonyms:4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate

Chemical Property of 4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate

There total 4 articles about 4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate 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: 80.0%

diphenylcarbamic chloride (83-01-2) + 4-amino-7-(2-deoxy-β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidin-2(3H)-one (103173-80-4) → 4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate (198008-12-7)

Guidance literature:

With pyridine; N-ethyl-N,N-diisopropylamine; Ambient temperature;

DOI:10.1039/a704866a

Reference yield: 80.0%

diphenylcarbamic chloride (83-01-2) + 4-amino-7-(2'-deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-2H-pyrrolo<2,3-d>pyrimidin-2-one (103173-80-4) → 4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate (198008-12-7) + 4-amino-7-(2-deoxy-5-O-(diphenylcarbamoyl)-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate

Guidance literature:

With pyridine; N-ethyl-N,N-diisopropylamine; at 20 ℃; for 2h;

DOI:10.1002/(SICI)1522-2675(19990505)82:5<726::AID-HLCA726>3.0.CO;2-K

Reference yield:

(2R,3S,5R)-5-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate (104291-20-5) → 4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate (198008-12-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / NH₃; H₂O / dioxane / 70 h / 120 °C

2: 67 percent / NaNO₂; AcOH / H₂O / 1.83 h / 20 °C

3: 80 percent / pyridine; i-Pr₂EtN / 2 h / 20 °C

With pyridine; ammonia; water; acetic acid; N-ethyl-N,N-diisopropylamine; sodium nitrite; In 1,4-dioxane; water; 1: Substitution / 2: Substitution / 3: Acylation;

DOI:10.1002/(SICI)1522-2675(19990505)82:5<726::AID-HLCA726>3.0.CO;2-K

upstream raw materials:

diphenylcarbamic chloride

4-amino-7-(2-deoxy-β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidin-2(3H)-one

4-amino-7-(2'-deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-2H-pyrrolo<2,3-d>pyrimidin-2-one

(2R,3S,5R)-5-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol

Downstream raw materials:

7-(2-deoxy-β-D-erythro-pentofuranosyl)-4-[(2-methylpropanoyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate

diphenyl-carbamic acid 4-(dibutylamino-methyleneamino)-7-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl ester

7-(2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl)-4-[(2-methylpropanoyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate