(2R,3S,5R)-5-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

Base Information

• Chemical Name: (2R,3S,5R)-5-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate
• CAS No.: 178420-94-5
• Molecular Formula: C₂₇H₂₃ClIN₃O₅
• Molecular Weight: 631.854
• Mol file: 178420-94-5.mol

Synonyms:(2R,3S,5R)-5-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

Chemical Property of (2R,3S,5R)-5-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,5R)-5-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

There total 8 articles about (2R,3S,5R)-5-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate 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: 73.0%

4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (123148-78-7) + 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) → (2R,3S,5R)-5-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate (178420-94-5)

Guidance literature:

4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine; With sodium hydride; In acetonitrile; at 20 ℃; for 0.5h;

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride; In acetonitrile; at 50 ℃; for 2h; Inert atmosphere;

DOI:10.1002/chem.201103419

Reference yield:

7-deazahypoxanthine (3680-71-5) → (2R,3S,5R)-5-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate (178420-94-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trichlorophosphate / 0.75 h / 115 °C

2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

3.1: sodium hydride / acetonitrile; mineral oil / 0.5 h / 20 °C / Inert atmosphere

3.2: 2.33 h / 20 °C

With N-iodo-succinimide; sodium hydride; trichlorophosphate; In N,N-dimethyl-formamide; acetonitrile; mineral oil;

Reference yield:

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) → (2R,3S,5R)-5-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate (178420-94-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetyl chloride / methanol / 1.17 h / 20 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

1.3: 0 °C / Inert atmosphere

2.1: sodium hydride / acetonitrile / 0.5 h / 20 °C

2.2: 2 h / 50 °C / Inert atmosphere

With sodium hydride; acetyl chloride; In methanol; acetonitrile;

DOI:10.1002/chem.201103419

upstream raw materials:

4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

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

D-2-deoxyribose

4-methyl-benzoyl chloride

Downstream raw materials:

7-deaza-2'-deoxy-7-iodoadenosine

5',3'-di-O-p-toluoyl-6-chloro-7-N-(t-butoxycarbonyl)aniline-7-deazapurine-2'-deoxyriboside

C₄₇H₅₁N₆O₆P

(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6H-2,3,5,6-tetraaza-aceanthrylen-2-yl)-tetrahydro-furan-3-ol