3-(O,O-diethylphosphonothio)difluoromethyl-1,2-O-isopropylidene-5-O-(4-chlorobenzoyl)-α-D-allofuranose

Base Information

• Chemical Name: 3-(O,O-diethylphosphonothio)difluoromethyl-1,2-O-isopropylidene-5-O-(4-chlorobenzoyl)-α-D-allofuranose
• CAS No.: 716357-05-0
• Molecular Formula: C₂₀H₂₆ClF₂O₈PS
• Molecular Weight: 530.911
• Mol file: 716357-05-0.mol

Synonyms:3-(O,O-diethylphosphonothio)difluoromethyl-1,2-O-isopropylidene-5-O-(4-chlorobenzoyl)-α-D-allofuranose

Chemical Property of 3-(O,O-diethylphosphonothio)difluoromethyl-1,2-O-isopropylidene-5-O-(4-chlorobenzoyl)-α-D-allofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(O,O-diethylphosphonothio)difluoromethyl-1,2-O-isopropylidene-5-O-(4-chlorobenzoyl)-α-D-allofuranose

There total 1 articles about 3-(O,O-diethylphosphonothio)difluoromethyl-1,2-O-isopropylidene-5-O-(4-chlorobenzoyl)-α-D-allofuranose 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: 72.0%

O,O-diethyl 1,1-difluoro-1-bromomethane phosphonothioate (180627-08-1) + 5-O-(4-chlorobenzoyl)-1,2-O-isopropylidene-α-D-pentofuranose-3-urose (199787-15-0) → 3-(O,O-diethylphosphonothio)difluoromethyl-1,2-O-isopropylidene-5-O-(4-chlorobenzoyl)-α-D-allofuranose (716357-05-0)

Guidance literature:

With isopropylmagnesium chloride; In tetrahydrofuran; diethyl ether; at -45 ℃; for 5h;

DOI:10.1016/j.tet.2004.03.082

Reference yield: 64.0%

3-(O,O-diethylphosphonothio)difluoromethyl-1,2-O-isopropylidene-5-O-(4-chlorobenzoyl)-α-D-allofuranose (716357-05-0) → 3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-1,2-O-isopropylidene-5-O-(4-chlorobenzoyl)-α-D-ribofuranose (716357-07-2)

Guidance literature:

3-(O,O-diethylphosphonothio)difluoromethyl-1,2-O-isopropylidene-5-O-(4-chlorobenzoyl)-α-D-allofuranose; With isopropylmagnesium chloride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 1h;

With monomethyl oxalyl chloride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.333333h;

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 2.33333h; Further stages.;

DOI:10.1016/j.tet.2004.03.082

Reference yield:

3-(O,O-diethylphosphonothio)difluoromethyl-1,2-O-isopropylidene-5-O-(4-chlorobenzoyl)-α-D-allofuranose (716357-05-0) → 5-O-(4-chlorobenzoyl)-1,2-di-O-acetyl-3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-β-D-ribofuranose (716357-09-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: i-PrMgCl / tetrahydrofuran; diethyl ether / 1 h / 0 °C

1.2: methyl oxalyl chloride / tetrahydrofuran; diethyl ether / 0.33 h / 0 °C

1.3: 64 percent / (n-Bu)3SnH; AIBN / toluene / 2.33 h

2.1: 77 percent / AcOH; H₂SO₄ / 20 °C

With sulfuric acid; isopropylmagnesium chloride; acetic acid; In tetrahydrofuran; diethyl ether;

DOI:10.1016/j.tet.2004.03.082

upstream raw materials:

O,O-diethyl 1,1-difluoro-1-bromomethane phosphonothioate

5-O-(4-chlorobenzoyl)-1,2-O-isopropylidene-α-D-pentofuranose-3-urose

Downstream raw materials:

3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-1,2-O-isopropylidene-5-O-(4-chlorobenzoyl)-α-D-ribofuranose

5-O-(4-chlorobenzoyl)-1,2-di-O-acetyl-3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-β-D-ribofuranose