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

Base Information

• Chemical Name: Toluene-4-sulfonic acid (S)-2-azido-2-((3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester
• CAS No.: 511269-83-3
• Molecular Formula: C₁₇H₂₃N₃O₇S
• Molecular Weight: 413.452
• Mol file: 511269-83-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (S)-2-azido-2-((3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester

There total 6 articles about Toluene-4-sulfonic acid (S)-2-azido-2-((3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-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: 95.0%

1,2-O-isopropylidene-3-O-methyl-6-O-tosyl-5-O-trifluoromethanesulfonyl-α-D-glucofuranose (511269-81-1) → Toluene-4-sulfonic acid (S)-2-azido-2-((3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester (511269-83-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1016/S0040-4020(02)01294-2

Reference yield:

1,2-O-isopropylidene-3-O-methyl-6-O-(p-toluenesulfonyl)-α-D-glucofuranose (32579-95-6) → Toluene-4-sulfonic acid (S)-2-azido-2-((3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester (511269-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / pyridine / CH₂Cl₂ / 1 h / -18 °C

2: 95 percent / NaN₃ / dimethylformamide / 4 h / 20 °C

With pyridine; sodium azide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(02)01294-2

Reference yield:

D-glucose (50-99-7) → Toluene-4-sulfonic acid (S)-2-azido-2-((3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester (511269-83-3)

Guidance literature:

Multi-step reaction with 6 steps

1: sulfuric acid / 5 h / 20 °C

2: 94 percent / KOH; tetrabutylammonium bromide / acetone / 0 - 20 °C

3: 90 percent / H₂O; AcOH / 0.83 h / 60 °C

4: 94 percent / pyridine / 4 h / -18 °C

5: 100 percent / pyridine / CH₂Cl₂ / 1 h / -18 °C

6: 95 percent / NaN₃ / dimethylformamide / 4 h / 20 °C

With pyridine; potassium hydroxide; sodium azide; sulfuric acid; tetrabutylammomium bromide; water; acetic acid; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(02)01294-2

upstream raw materials:

1,2-O-isopropylidene-3-O-methyl-6-O-tosyl-5-O-trifluoromethanesulfonyl-α-D-glucofuranose

1,2-O-isopropylidene-3-O-methyl-6-O-(p-toluenesulfonyl)-α-D-glucofuranose

D-glucose

1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose