4-chloro-7-[methyl 3,5-bis-O-(2,4-dichlorobenzyl)-α-D-arabinofuranosid-2-yl]-7H-pyrrolo[2,3-d]pyrimidine

Base Information

• Chemical Name: 4-chloro-7-[methyl 3,5-bis-O-(2,4-dichlorobenzyl)-α-D-arabinofuranosid-2-yl]-7H-pyrrolo[2,3-d]pyrimidine
• CAS No.: 1312805-14-3
• Molecular Formula: C₂₆H₂₂Cl₅N₃O₄
• Molecular Weight: 617.743
• Mol file: 1312805-14-3.mol

Synonyms:4-chloro-7-[methyl 3,5-bis-O-(2,4-dichlorobenzyl)-α-D-arabinofuranosid-2-yl]-7H-pyrrolo[2,3-d]pyrimidine

Chemical Property of 4-chloro-7-[methyl 3,5-bis-O-(2,4-dichlorobenzyl)-α-D-arabinofuranosid-2-yl]-7H-pyrrolo[2,3-d]pyrimidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-chloro-7-[methyl 3,5-bis-O-(2,4-dichlorobenzyl)-α-D-arabinofuranosid-2-yl]-7H-pyrrolo[2,3-d]pyrimidine

There total 4 articles about 4-chloro-7-[methyl 3,5-bis-O-(2,4-dichlorobenzyl)-α-D-arabinofuranosid-2-yl]-7H-pyrrolo[2,3-d]pyrimidine 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: 87.0%

methyl 3,5-bis-O-(2,4-dichlorobenzyl)-2-O-(trifluoromethylsulfonyl)-α-D-ribofuranoside (1312805-13-2) + 4-chloro-1H-pyrrolo[2,3-d]pyrimidine (3680-69-1) → 4-chloro-7-[methyl 3,5-bis-O-(2,4-dichlorobenzyl)-α-D-arabinofuranosid-2-yl]-7H-pyrrolo[2,3-d]pyrimidine (1312805-14-3)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1055/s-0030-1259961

Reference yield:

methyl 2,3,5-tris-O-(2,4-dichlorobenzyl)-β-D-ribofuranoside (163759-40-8) → 4-chloro-7-[methyl 3,5-bis-O-(2,4-dichlorobenzyl)-α-D-arabinofuranosid-2-yl]-7H-pyrrolo[2,3-d]pyrimidine (1312805-14-3)

Guidance literature:

Multi-step reaction with 3 steps

1: tin(IV) chloride / dichloromethane / 28 h / 0 °C / Inert atmosphere

2: pyridine / 1 h / -40 - 0 °C / Inert atmosphere

3: caesium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere

With pyridine; tin(IV) chloride; caesium carbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-0030-1259961

Reference yield:

1-O-methyl-D-ribofuranose (7473-45-2) → 4-chloro-7-[methyl 3,5-bis-O-(2,4-dichlorobenzyl)-α-D-arabinofuranosid-2-yl]-7H-pyrrolo[2,3-d]pyrimidine (1312805-14-3)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 13 h / 0 - 20 °C

2: tin(IV) chloride / dichloromethane / 28 h / 0 °C / Inert atmosphere

3: pyridine / 1 h / -40 - 0 °C / Inert atmosphere

4: caesium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere

With pyridine; tin(IV) chloride; sodium hydride; caesium carbonate; In dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1055/s-0030-1259961

upstream raw materials:

methyl 3,5-bis-O-(2,4-dichlorobenzyl)-2-O-(trifluoromethylsulfonyl)-α-D-ribofuranoside

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

(3R,4S,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxytetrahydrofuran-3-ol

methyl 2,3,5-tris-O-(2,4-dichlorobenzyl)-β-D-ribofuranoside

Downstream raw materials:

4-amino-7-[methyl 3,5-bis-O-(2,4-dichlorobenzyl)-α-D-arabinofuranosid-2-yl]-7H-pyrrolo[2,3-d]pyrimidine

7-[methyl 3,5-bis-O-(2,4-dichlorobenzyl)-α-D-arabinofuranosid-2-yl]-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine