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

Base Information

• Chemical Name: methyl 3,5-bis-O-(2,4-dichlorobenzyl)-2-O-(trifluoromethylsulfonyl)-α-D-ribofuranoside
• CAS No.: 1312805-13-2
• Molecular Formula: C₂₁H₁₉Cl₄F₃O₇S
• Molecular Weight: 614.251
• Mol file: 1312805-13-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about methyl 3,5-bis-O-(2,4-dichlorobenzyl)-2-O-(trifluoromethylsulfonyl)-α-D-ribofuranoside 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: 74.0%

trifluoromethylsulfonic anhydride (358-23-6) + (3R,4S,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxytetrahydrofuran-3-ol (168427-35-8) → methyl 3,5-bis-O-(2,4-dichlorobenzyl)-2-O-(trifluoromethylsulfonyl)-α-D-ribofuranoside (1312805-13-2)

Guidance literature:

With pyridine; at -40 - 0 ℃; for 1h; Inert atmosphere;

DOI:10.1055/s-0030-1259961

Reference yield:

1-O-methyl-D-ribofuranose (7473-45-2) → methyl 3,5-bis-O-(2,4-dichlorobenzyl)-2-O-(trifluoromethylsulfonyl)-α-D-ribofuranoside (1312805-13-2)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1055/s-0030-1259961

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

upstream raw materials:

trifluoromethylsulfonic anhydride

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

1-O-methyl-D-ribofuranose

Downstream raw materials:

3-[methyl α-D-arabinofuranosid-2-yl]adenine

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

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