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

Base Information

• Chemical Name: 5',3'-di-O-p-toluoyl-6-chloro-7-N-(t-butoxycarbonyl)aniline-7-deazapurine-2'-deoxyriboside
• CAS No.: 258836-83-8
• Molecular Formula: C₃₈H₃₇ClN₄O₇
• Molecular Weight: 697.187
• Mol file: 258836-83-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about 5',3'-di-O-p-toluoyl-6-chloro-7-N-(t-butoxycarbonyl)aniline-7-deazapurine-2'-deoxyriboside 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: 68.0%

N-tert-butoxycarbonyl-2-trimethylstannylaniline (114552-32-8) + (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) → 5',3'-di-O-p-toluoyl-6-chloro-7-N-(t-butoxycarbonyl)aniline-7-deazapurine-2'-deoxyriboside (258836-83-8)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 60 ℃; for 24h;

DOI:10.1016/S0040-4039(99)01875-4

Reference yield: 55.0%

tributyl (o-tert-butyloxycarbonylaminophenyl) stannane (148493-54-3) + (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) → 5',3'-di-O-p-toluoyl-6-chloro-7-N-(t-butoxycarbonyl)aniline-7-deazapurine-2'-deoxyriboside (258836-83-8)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride; In N,N-dimethyl-formamide; at 100 ℃; for 1h; Inert atmosphere;

DOI:10.1002/chem.201103419

Reference yield:

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) → 5',3'-di-O-p-toluoyl-6-chloro-7-N-(t-butoxycarbonyl)aniline-7-deazapurine-2'-deoxyriboside (258836-83-8)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 2 h / 50 °C / Inert atmosphere

2.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; cesium fluoride; In N,N-dimethyl-formamide; acetonitrile; 2.1: Stille coupling;

DOI:10.1002/chem.201103419

upstream raw materials:

N-tert-butoxycarbonyl-2-trimethylstannylaniline

(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

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

4-methyl-benzoyl chloride

Downstream raw materials:

C₃₃H₂₈N₄O₅

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