Toluene-4-sulfonic acid (4S,5R)-2,2-dimethyl-5-((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-[1,3]dioxolan-4-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (4S,5R)-2,2-dimethyl-5-((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-[1,3]dioxolan-4-ylmethyl ester
• CAS No.: 207454-76-0
• Molecular Formula: C₂₄H₃₄O₁₀S
• Molecular Weight: 514.594
• Mol file: 207454-76-0.mol

Synonyms:

Chemical Property of Toluene-4-sulfonic acid (4S,5R)-2,2-dimethyl-5-((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-[1,3]dioxolan-4-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (4S,5R)-2,2-dimethyl-5-((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-[1,3]dioxolan-4-ylmethyl ester

There total 1 articles about Toluene-4-sulfonic acid (4S,5R)-2,2-dimethyl-5-((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-[1,3]dioxolan-4-ylmethyl 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: 91.0%

p-toluenesulfonyl chloride (98-59-9) + [(4S,5R)-2,2-Dimethyl-5-((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-[1,3]dioxolan-4-yl]-methanol (177421-51-1) → Toluene-4-sulfonic acid (4S,5R)-2,2-dimethyl-5-((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-[1,3]dioxolan-4-ylmethyl ester (207454-76-0)

Guidance literature:

With pyridine; for 20h; Ambient temperature;

DOI:10.1016/S0957-4166(98)00064-0

Reference yield:

Toluene-4-sulfonic acid (4S,5R)-2,2-dimethyl-5-((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-[1,3]dioxolan-4-ylmethyl ester (207454-76-0) → (2R,3S,4S)-3,4-Dihydroxy-2-((1R,2S,3R)-1,2,3,4-tetrahydroxy-butyl)-pyrrolidine-1-carboxylic acid benzyl ester (207454-81-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / NaN₃ / dimethylformamide / 15 h / 80 °C

2: 84 percent / 70percent aq. AcOH / 22 h / 100 °C

3: 88 percent / H₂ / 10percent Pd/C / H₂O / 20 h

4: 81.6 percent / NaHCO₃ / H₂O / 6 h

With sodium azide; hydrogen; sodium hydrogencarbonate; acetic acid; palladium on activated charcoal; In water; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(98)00064-0

Reference yield:

Toluene-4-sulfonic acid (4S,5R)-2,2-dimethyl-5-((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-[1,3]dioxolan-4-ylmethyl ester (207454-76-0) → (2R,3S,4S)-3,4-Dihydroxy-2-[(1R,2S,3R)-1,2,3-trihydroxy-4-(2,4,6-trimethyl-benzenesulfonyloxy)-butyl]-pyrrolidine-1-carboxylic acid benzyl ester (207454-82-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / NaN₃ / dimethylformamide / 15 h / 80 °C

2: 84 percent / 70percent aq. AcOH / 22 h / 100 °C

3: 88 percent / H₂ / 10percent Pd/C / H₂O / 20 h

4: 81.6 percent / NaHCO₃ / H₂O / 6 h

5: 69.4 percent / pyridine, DMAP / 15 h / Ambient temperature

With pyridine; dmap; sodium azide; hydrogen; sodium hydrogencarbonate; acetic acid; palladium on activated charcoal; In water; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(98)00064-0

upstream raw materials:

p-toluenesulfonyl chloride

[(4S,5R)-2,2-Dimethyl-5-((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-[1,3]dioxolan-4-yl]-methanol

Downstream raw materials:

(2R,3S,4S)-3,4-Dihydroxy-2-((1R,2S,3R)-1,2,3,4-tetrahydroxy-butyl)-pyrrolidine-1-carboxylic acid benzyl ester

(2R,3S,4S)-3,4-Dihydroxy-2-[(1R,2S,3R)-1,2,3-trihydroxy-4-(2,4,6-trimethyl-benzenesulfonyloxy)-butyl]-pyrrolidine-1-carboxylic acid benzyl ester