Benzoic acid (2R,3R,4S)-2-(2-benzyloxy-ethyl)-4-(imidazole-1-carbothioyloxy)-tetrahydro-furan-3-yl ester

Base Information

Chemical Name:Benzoic acid (2R,3R,4S)-2-(2-benzyloxy-ethyl)-4-(imidazole-1-carbothioyloxy)-tetrahydro-furan-3-yl ester
CAS No.:250697-00-8
Molecular Formula:C₂₄H₂₄N₂O₅S
Molecular Weight:452.531
Hs Code.:

Synonyms:Benzoic acid (2R,3R,4S)-2-(2-benzyloxy-ethyl)-4-(imidazole-1-carbothioyloxy)-tetrahydro-furan-3-yl ester

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Chemical Property of Benzoic acid (2R,3R,4S)-2-(2-benzyloxy-ethyl)-4-(imidazole-1-carbothioyloxy)-tetrahydro-furan-3-yl ester

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Technology Process of Benzoic acid (2R,3R,4S)-2-(2-benzyloxy-ethyl)-4-(imidazole-1-carbothioyloxy)-tetrahydro-furan-3-yl ester

There total 10 articles about Benzoic acid (2R,3R,4S)-2-(2-benzyloxy-ethyl)-4-(imidazole-1-carbothioyloxy)-tetrahydro-furan-3-yl 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: 82.0%

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 250696-88-9
6-O-benzyl-3-O-benzoyl-1,5-dideoxy-D-allofuranose

: 250697-00-8
Benzoic acid (2R,3R,4S)-2-(2-benzyloxy-ethyl)-4-(imidazole-1-carbothioyloxy)-tetrahydro-furan-3-yl ester

Guidance literature:: In 1,2-dichloro-ethane; for 3h; Heating;
DOI:10.1080/07328319908044857

Reference yield:

: 29474-73-5
(+)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl benzoate

: 250697-00-8
Benzoic acid (2R,3R,4S)-2-(2-benzyloxy-ethyl)-4-(imidazole-1-carbothioyloxy)-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 76 percent / 0.4 percent HCl / acetonitrile; H₂O / 8 h / 20 °C

2: 92 percent / imidazole / dimethylformamide; CH₂Cl₂ / -15 - 0 °C

3: 89 percent / 1,2-dichloro-ethane / 4 h / Heating

4: 87 percent / n-Bu₃SnH; AIBN / toluene / 3 h / Heating

5: 78 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

6: 6.07 g / NaH / tetrahydrofuran / 20 °C

7: 64 percent / TMSOTf; Et₃SiH / CH₂Cl₂ / -15 - 20 °C

8: 82 percent / 1,2-dichloro-ethane / 3 h / Heating

With 1H-imidazole; hydrogenchloride; triethylsilane; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Hydrolysis / 2: Silylation / 3: Esterification / 4: Reduction / 5: Desilylation / 6: Benzylation / 7: Reductive cleavage / 8: Esterification;
DOI:10.1080/07328319908044857

Reference yield:

: 31795-13-8
3-O-benzoyl-1,2-O-isopropylidene-α-D-allofuranose

: 250697-00-8
Benzoic acid (2R,3R,4S)-2-(2-benzyloxy-ethyl)-4-(imidazole-1-carbothioyloxy)-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / imidazole / dimethylformamide; CH₂Cl₂ / -15 - 0 °C

2: 89 percent / 1,2-dichloro-ethane / 4 h / Heating

3: 87 percent / n-Bu₃SnH; AIBN / toluene / 3 h / Heating

4: 78 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

5: 6.07 g / NaH / tetrahydrofuran / 20 °C

6: 64 percent / TMSOTf; Et₃SiH / CH₂Cl₂ / -15 - 20 °C

7: 82 percent / 1,2-dichloro-ethane / 3 h / Heating

With 1H-imidazole; triethylsilane; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 1: Silylation / 2: Esterification / 3: Reduction / 4: Desilylation / 5: Benzylation / 6: Reductive cleavage / 7: Esterification;
DOI:10.1080/07328319908044857