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

Base Information

• Chemical Name: (2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6H-2,3,5,6-tetraaza-aceanthrylen-2-yl)-tetrahydro-furan-3-ol
• CAS No.: 258836-90-7
• Molecular Formula: C₃₈H₃₄N₄O₅
• Molecular Weight: 626.712
• Mol file: 258836-90-7.mol

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

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

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6H-2,3,5,6-tetraaza-aceanthrylen-2-yl)-tetrahydro-furan-3-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: 68.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + (2R,3S,5R)-2-Hydroxymethyl-5-(6H-2,3,5,6-tetraaza-aceanthrylen-2-yl)-tetrahydro-furan-3-ol (258836-80-5) → (2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6H-2,3,5,6-tetraaza-aceanthrylen-2-yl)-tetrahydro-furan-3-ol (258836-90-7)

Guidance literature:

With pyridine; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/chem.201103419

Reference yield:

(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) → (2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6H-2,3,5,6-tetraaza-aceanthrylen-2-yl)-tetrahydro-furan-3-ol (258836-90-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 68 percent / (Ph₃P)2PdCl₂ / dimethylformamide / 24 h / 60 °C

2.1: Dabco; DBU / dimethylformamide / 21 h / 75 °C

2.2: 96 percent / aq. TFA / CH₂Cl₂ / 3 h / 20 °C

3.1: 64 percent / NaOMe; MeOH / 20 °C

4.1: 65 percent / pyridine

With 1,4-diaza-bicyclo[2.2.2]octane; methanol; bis-triphenylphosphine-palladium(II) chloride; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; N,N-dimethyl-formamide; 1.1: Arylation / 2.1: Cyclization / 2.2: Hydrolysis / 3.1: Hydrolysis / 4.1: Alkylation;

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

Reference yield:

5',3'-di-O-p-toluoyl-6-chloro-7-N-(t-butoxycarbonyl)aniline-7-deazapurine-2'-deoxyriboside (258836-83-8) → (2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6H-2,3,5,6-tetraaza-aceanthrylen-2-yl)-tetrahydro-furan-3-ol (258836-90-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Dabco; DBU / dimethylformamide / 21 h / 75 °C

1.2: 96 percent / aq. TFA / CH₂Cl₂ / 3 h / 20 °C

2.1: 64 percent / NaOMe; MeOH / 20 °C

3.1: 65 percent / pyridine

With 1,4-diaza-bicyclo[2.2.2]octane; methanol; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; N,N-dimethyl-formamide; 1.1: Cyclization / 1.2: Hydrolysis / 2.1: Hydrolysis / 3.1: Alkylation;

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

upstream raw materials:

4,4'-dimethoxytrityl chloride

(2R,3S,5R)-2-Hydroxymethyl-5-(6H-2,3,5,6-tetraaza-aceanthrylen-2-yl)-tetrahydro-furan-3-ol

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

Downstream raw materials:

C₄₇H₅₁N₆O₆P