phenyl 5-O-benzyl-1,2,3-trideoxy-3-fluoro-1-seleno-β-D-erythro-pentofuranoside

Base Information

• Chemical Name: phenyl 5-O-benzyl-1,2,3-trideoxy-3-fluoro-1-seleno-β-D-erythro-pentofuranoside
• CAS No.: 220718-09-2
• Molecular Formula: C₁₈H₁₉FO₂Se
• Molecular Weight: 365.306
• Mol file: 220718-09-2.mol

Synonyms:phenyl 5-O-benzyl-1,2,3-trideoxy-3-fluoro-1-seleno-β-D-erythro-pentofuranoside

Chemical Property of phenyl 5-O-benzyl-1,2,3-trideoxy-3-fluoro-1-seleno-β-D-erythro-pentofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 5-O-benzyl-1,2,3-trideoxy-3-fluoro-1-seleno-β-D-erythro-pentofuranoside

There total 3 articles about phenyl 5-O-benzyl-1,2,3-trideoxy-3-fluoro-1-seleno-β-D-erythro-pentofuranoside 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: 62.0%

Benzeneselenol (645-96-5) + methyl 5-O-benzyl-2,3-dideoxy-3-fluoro-α-D-erythro-pentofuranoside (220718-08-1) → phenyl 5-O-benzyl-1,2,3-trideoxy-3-fluoro-1-seleno-α-D-erythro-pentofuranoside (220718-10-5) + phenyl 5-O-benzyl-1,2,3-trideoxy-3-fluoro-1-seleno-β-D-erythro-pentofuranoside (220718-09-2)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jo980911f

Reference yield:

methyl 5-O-benzyl-3-fluoro-3-deoxy-α-D-arabino-furanoside (14980-09-7) → phenyl 5-O-benzyl-1,2,3-trideoxy-3-fluoro-1-seleno-β-D-erythro-pentofuranoside (220718-09-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / toluene / 1 h / 0 °C

1.2: toluene / 2 h / 20 °C

2.1: 3.15 g / tri-n-butyltin hydride; AIBN / toluene / 5 h / Heating

3.1: 33.5 percent / boron trifluoride ethyl etherate / CH₂Cl₂ / 1 h / 20 °C

With 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; sodium hydride; In dichloromethane; toluene; 1.1: Addition / 1.2: Methylation / 2.1: Barton's deoxygenation / 3.1: Condensation;

DOI:10.1021/jo980911f

Reference yield:

dithiocarbonic acid O-(5-benzyloxymethyl-4-fluoro-2-methoxy-tetrahydro-furan-3-yl) ester S-methyl ester → phenyl 5-O-benzyl-1,2,3-trideoxy-3-fluoro-1-seleno-β-D-erythro-pentofuranoside (220718-09-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.15 g / tri-n-butyltin hydride; AIBN / toluene / 5 h / Heating

2: 33.5 percent / boron trifluoride ethyl etherate / CH₂Cl₂ / 1 h / 20 °C

With 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; In dichloromethane; toluene; 1: Barton's deoxygenation / 2: Condensation;

DOI:10.1021/jo980911f

upstream raw materials:

Benzeneselenol

methyl 5-O-benzyl-2,3-dideoxy-3-fluoro-α-D-erythro-pentofuranoside

methyl 5-O-benzyl-3-fluoro-3-deoxy-α-D-arabino-furanoside

Downstream raw materials:

2-benzyloxymethylfuran