Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-((3aR,5S,6S,6aR)-2,2-dimethyl-6-vinyloxy-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-vinyloxy-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester
• CAS No.: 189367-65-5
• Molecular Formula: C₂₄H₃₈O₈SSi
• Molecular Weight: 514.712

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

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

There total 5 articles about Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-((3aR,5S,6S,6aR)-2,2-dimethyl-6-vinyloxy-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: 87.0%

Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(3aR,5S,6S,6aR)-6-(1-ethoxy-ethoxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethyl ester (189367-64-4) → Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-((3aR,5S,6S,6aR)-2,2-dimethyl-6-vinyloxy-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester (189367-65-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(97)00248-2

Reference yield:

5-azido-5-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-glucofuranose (4056-11-5) → Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-((3aR,5S,6S,6aR)-2,2-dimethyl-6-vinyloxy-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester (189367-65-5)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; triethylamine; trifluoroacetic acid; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(97)00248-2

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-((3aR,5S,6S,6aR)-2,2-dimethyl-6-vinyloxy-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester (189367-65-5)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; triethylamine; trifluoroacetic acid; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(97)00248-2

upstream raw materials:

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

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

tert-butyldimethylsilyl chloride

1,2-O-isopropylidene-5-O-tosyl-α-D-glucuronolactone

Downstream raw materials:

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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