Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-((R)-4-oxo-azetidin-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-((R)-4-oxo-azetidin-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethyl ester
CAS No.:189367-66-6
Molecular Formula:C₂₅H₃₉NO₉SSi
Molecular Weight:557.737
Hs Code.:

Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-((R)-4-oxo-azetidin-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethyl ester

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Chemical Property of Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-((R)-4-oxo-azetidin-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethyl ester

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Technology Process of Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-((R)-4-oxo-azetidin-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethyl ester

There total 6 articles about Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-((R)-4-oxo-azetidin-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxol-5-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:

: 4056-11-5
5-azido-5-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-glucofuranose

: 189367-66-6
Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-((R)-4-oxo-azetidin-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / imidazole / acetonitrile / 1) 0 deg C -> room temperature, 2) room temperature, 3 h

2: 97 percent / CF₃CO₂H / 120 h / Ambient temperature

3: 87 percent / Et₃N, TMSOTf / CH₂Cl₂ / 2 h / 0 °C

4: 1) Na₂CO₃, 2) Red-Al / 1) toluene, -70 deg C, 3 h, 2) toluene, -70 deg C, 30 min

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; sodium carbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; In dichloromethane; acetonitrile;
DOI:10.1016/S0040-4020(97)00248-2

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 189367-66-6
Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-((R)-4-oxo-azetidin-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / imidazole / acetonitrile / 1) 0 deg C -> room temperature, 2) room temperature, 3 h

2: 97 percent / CF₃CO₂H / 120 h / Ambient temperature

3: 87 percent / Et₃N, TMSOTf / CH₂Cl₂ / 2 h / 0 °C

4: 1) Na₂CO₃, 2) Red-Al / 1) toluene, -70 deg C, 3 h, 2) toluene, -70 deg C, 30 min

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; sodium carbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; In dichloromethane; acetonitrile;
DOI:10.1016/S0040-4020(97)00248-2

Reference yield:

: 55263-78-0
1,2-O-isopropylidene-5-O-tosyl-α-D-glucuronolactone

: 189367-66-6
Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-((R)-4-oxo-azetidin-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / NaBH₄ / tetrahydrofuran; H₂O / 1 h / 0 °C

2: 89 percent / imidazole / acetonitrile / 1) 0 deg C -> room temperature, 2) room temperature, 3 h

3: 97 percent / CF₃CO₂H / 120 h / Ambient temperature

4: 87 percent / Et₃N, TMSOTf / CH₂Cl₂ / 2 h / 0 °C

5: 1) Na₂CO₃, 2) Red-Al / 1) toluene, -70 deg C, 3 h, 2) toluene, -70 deg C, 30 min

With 1H-imidazole; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; sodium carbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1016/S0040-4020(97)00248-2