Benzoic acid 2-[(2R,3R,4S)-4-hydroxy-3-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-ethyl ester

Base Information

Chemical Name:Benzoic acid 2-[(2R,3R,4S)-4-hydroxy-3-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-ethyl ester
CAS No.:289665-47-0
Molecular Formula:C₂₀H₂₂O₇S
Molecular Weight:406.456
Hs Code.:

Synonyms:Benzoic acid 2-[(2R,3R,4S)-4-hydroxy-3-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-ethyl ester

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Chemical Property of Benzoic acid 2-[(2R,3R,4S)-4-hydroxy-3-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-ethyl ester

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Technology Process of Benzoic acid 2-[(2R,3R,4S)-4-hydroxy-3-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-ethyl ester

There total 5 articles about Benzoic acid 2-[(2R,3R,4S)-4-hydroxy-3-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-ethyl ester 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: 53.0%

: 289665-46-9
6-benzoyl-1,2-O-isopropylidene-3-O-tosyl-5-deoxy-α-D-glucofuranose

: 289665-47-0
Benzoic acid 2-[(2R,3R,4S)-4-hydroxy-3-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-ethyl ester

: 289665-48-1
C₄₀H₄₂O₁₄S₂

Guidance literature:: 6-benzoyl-1,2-O-isopropylidene-3-O-tosyl-5-deoxy-α-D-glucofuranose; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 0.5h;

With triethylsilane; In dichloromethane; at 0 ℃; for 48h;
DOI:10.1016/S0957-4166(00)00136-1

Reference yield:

: 62102-11-8
5-deoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-xylo-hexofuranose

: 289665-47-0
Benzoic acid 2-[(2R,3R,4S)-4-hydroxy-3-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 98 percent / pyridine / 18 h / 20 °C

2.1: TMSOTf / CH₂Cl₂ / 0.5 h / 20 °C

2.2: 53 percent / Et₃SiH / CH₂Cl₂ / 48 h / 0 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; 1.1: Esterification / 2.1: Ring cleavage / 2.2: Reduction;
DOI:10.1016/S0957-4166(00)00136-1

Reference yield:

: 43138-33-6
5β-vinyl-4β-tosyl-2α,3α-O-isopropylidene tetrahydrofuran

: 289665-47-0
Benzoic acid 2-[(2R,3R,4S)-4-hydroxy-3-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: BH₃*SMe₂ / tetrahydrofuran / 2 h / 20 °C

1.2: 53.5 percent / NaOH; aq. H₂O₂ / methanol; tetrahydrofuran / 2 h / 20 °C

2.1: 98 percent / pyridine / 18 h / 20 °C

3.1: TMSOTf / CH₂Cl₂ / 0.5 h / 20 °C

3.2: 53 percent / Et₃SiH / CH₂Cl₂ / 48 h / 0 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; In tetrahydrofuran; dichloromethane; 1.1: Reduction / 1.2: Hydrolysis / 2.1: Esterification / 3.1: Ring cleavage / 3.2: Reduction;
DOI:10.1016/S0957-4166(00)00136-1