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

Base Information

Chemical Name:5-O-(4-chlorobenzoyl)-1,2-di-O-acetyl-3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-β-D-ribofuranose
CAS No.:716357-09-4
Molecular Formula:C₂₁H₂₆ClF₂O₉PS
Molecular Weight:558.922
Hs Code.:

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

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

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

There total 2 articles about 5-O-(4-chlorobenzoyl)-1,2-di-O-acetyl-3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-β-D-ribofuranose 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: 77.0%

: 108-24-7
acetic anhydride

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

: 716357-09-4
5-O-(4-chlorobenzoyl)-1,2-di-O-acetyl-3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-β-D-ribofuranose

Guidance literature:: With sulfuric acid; acetic acid; at 20 ℃;
DOI:10.1016/j.tet.2004.03.082

Reference yield:

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

: 716357-09-4
5-O-(4-chlorobenzoyl)-1,2-di-O-acetyl-3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-β-D-ribofuranose

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