methyl 4-[(3S,4S,5R)-3-hydroxy-1-(toluene-4-sulphonyl)-5-trityloxymethylpiperidin-4-yl]benzoate

Base Information

• Chemical Name: methyl 4-[(3S,4S,5R)-3-hydroxy-1-(toluene-4-sulphonyl)-5-trityloxymethylpiperidin-4-yl]benzoate
• CAS No.: 912347-29-6
• Molecular Formula: C₄₀H₃₉NO₆S
• Molecular Weight: 661.819
• Mol file: 912347-29-6.mol

Synonyms:methyl 4-[(3S,4S,5R)-3-hydroxy-1-(toluene-4-sulphonyl)-5-trityloxymethylpiperidin-4-yl]benzoate

Chemical Property of methyl 4-[(3S,4S,5R)-3-hydroxy-1-(toluene-4-sulphonyl)-5-trityloxymethylpiperidin-4-yl]benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-[(3S,4S,5R)-3-hydroxy-1-(toluene-4-sulphonyl)-5-trityloxymethylpiperidin-4-yl]benzoate

There total 1 articles about methyl 4-[(3S,4S,5R)-3-hydroxy-1-(toluene-4-sulphonyl)-5-trityloxymethylpiperidin-4-yl]benzoate 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:

methyl 4-[(3S,4S,5R)-3-hydroxy-5-hydroxymethyl-1-(toluene-4-sulphonyl)-piperidin-4-yl]-benzoate (912347-30-9) + trityl chloride (76-83-5) → methyl 4-[(3S,4S,5R)-3-hydroxy-1-(toluene-4-sulphonyl)-5-trityloxymethylpiperidin-4-yl]benzoate (912347-29-6)

Guidance literature:

With dmap; In pyridine; at 70 ℃; for 12h;

Reference yield:

methyl 4-[(3S,4S,5R)-3-hydroxy-1-(toluene-4-sulphonyl)-5-trityloxymethylpiperidin-4-yl]benzoate (912347-29-6) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → methyl 4-[(3S,4S,5R)-1-(toluene-4-sulphonyl)-3-triisopropylsilanyloxy-5-trityloxymethylpiperidin-4-yl]benzoate (912347-28-5)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 3.16667h;

Reference yield:

methyl 4-[(3S,4S,5R)-3-hydroxy-1-(toluene-4-sulphonyl)-5-trityloxymethylpiperidin-4-yl]benzoate (912347-29-6) → methyl 4-[(3R,4S,5S)-3-{2-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-ethyl}-1-(toluene-4-sulphonyl)-5-triisopropylsilanyloxypiperidin-4-yl]benzoate (912347-23-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 3.17 h / 0 °C

2.1: methanol; toluene-4-sulfonic acid / tetrahydrofuran / 20 h / 0 - 20 °C

3.1: 4-methylmorpholine N-oxide / dichloromethane / 0.17 h / 20 °C / Molecular sieve

3.2: 0.33 h / 20 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 20 °C

4.2: 4.17 h / 20 °C

5.1: hydrogen / palladium 10% on activated carbon / ethanol / 2 h / 20 °C

With 2,6-dimethylpyridine; methanol; n-butyllithium; hydrogen; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; palladium 10% on activated carbon; In tetrahydrofuran; ethanol; hexane; dichloromethane;

upstream raw materials:

methyl 4-[(3S,4S,5R)-3-hydroxy-5-hydroxymethyl-1-(toluene-4-sulphonyl)-piperidin-4-yl]-benzoate

trityl chloride

Downstream raw materials:

methyl 4-[(3S,4S,5R)-1-(toluene-4-sulphonyl)-3-triisopropylsilanyloxy-5-trityloxymethylpiperidin-4-yl]benzoate

methyl 4-[(3R,4S,5S)-3-formyl-1-(toluene-4-sulphonyl)-5-triisopropylsilanyloxypiperidin-4-yl]benzoate

methyl 4-[(3R,4S,5S)-3-hydroxymethyl-1-(toluene-4-sulphonyl)-5-triisopropylsilanyloxypiperidin-4-yl]benzoate

methyl 4-[(3R,4S,5S)-3-{2-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-ethyl}-1-(toluene-4-sulphonyl)-5-triisopropylsilanyloxypiperidin-4-yl]benzoate