BENZYL-3,5-DI-O-BENZYL-2-DEOXY-2-FLUORO-ALPHA-D-ARABINOFURANOSIDE

Base Information

• Chemical Name: BENZYL-3,5-DI-O-BENZYL-2-DEOXY-2-FLUORO-ALPHA-D-ARABINOFURANOSIDE
• CAS No.: 80765-80-6
• Molecular Formula: C26H27 F O4
• Molecular Weight: 422.496
• Mol file: 80765-80-6.mol

Synonyms:BENZYL-3,5-DI-O-BENZYL-2-DEOXY-2-FLUORO-ALPHA-D-ARABINOFURANOSIDE

Chemical Property of BENZYL-3,5-DI-O-BENZYL-2-DEOXY-2-FLUORO-ALPHA-D-ARABINOFURANOSIDE

Chemical Property:

• Boiling Point: 536.2±50.0 °C(Predicted)
• PSA: 36.92000
• Density: 1.19
• LogP: 5.06840

Purity/Quality:

98%,99%, ^*data from raw suppliers

BENZYL-3,5-DI-O-BENZYL-2-DEOXY-2-FLUORO-ALPHA-D-ARABINOFURANOSIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BENZYL-3,5-DI-O-BENZYL-2-DEOXY-2-FLUORO-ALPHA-D-ARABINOFURANOSIDE

There total 5 articles about BENZYL-3,5-DI-O-BENZYL-2-DEOXY-2-FLUORO-ALPHA-D-ARABINOFURANOSIDE 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: 50.0%

1,3,5-tri-O-benzyl-2-O-(trifluoromethanesulfonyl)-α-D-ribofuranose (80765-79-3) → 2-fluoro-2-deoxy-1,3,5-tri-O-benzoyl-α-D-arabinofuranose (80765-80-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -10 ℃; for 3h;

DOI:10.1021/jo00347a027

Reference yield:

(3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol (16054-77-6) → 2-fluoro-2-deoxy-1,3,5-tri-O-benzoyl-α-D-arabinofuranose (80765-80-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) dibutyltin oxide, 2.) potassium carbonate / 1.) methanol, reflux, 1.5 h, 2.) DMF, RT, 12 h

2: 89.7 percent / pyridine / CH₂Cl₂ / 1.5 h / -20 °C

3: 50 percent / tetra-n-butylammonium fluoride (TBAF) / tetrahydrofuran / 3 h / -10 °C

With pyridine; tetrabutyl ammonium fluoride; di(n-butyl)tin oxide; potassium carbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00347a027

Reference yield:

benzyl bromide (100-39-0) → 2-fluoro-2-deoxy-1,3,5-tri-O-benzoyl-α-D-arabinofuranose (80765-80-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) dibutyltin oxide, 2.) potassium carbonate / 1.) methanol, reflux, 1.5 h, 2.) DMF, RT, 12 h

2: 89.7 percent / pyridine / CH₂Cl₂ / 1.5 h / -20 °C

3: 50 percent / tetra-n-butylammonium fluoride (TBAF) / tetrahydrofuran / 3 h / -10 °C

With pyridine; tetrabutyl ammonium fluoride; di(n-butyl)tin oxide; potassium carbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00347a027

upstream raw materials:

1,3,5-tri-O-benzyl-2-O-(trifluoromethanesulfonyl)-α-D-ribofuranose

(3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol

benzyl bromide

3,5-O-dibenzyloxy-1,2-O-isorpopylidene-α-D-ribofuranose

Downstream raw materials:

1-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)uracil

(2R,3R,4S,5R)-1-(3-fluoro-4-hydroxy-5-(monophosphoryloxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Refernces