Toluene-4-sulfonic acid 4-((2R,3S)-3-benzyloxy-6-oxo-piperidin-2-yl)-butyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid 4-((2R,3S)-3-benzyloxy-6-oxo-piperidin-2-yl)-butyl ester
• CAS No.: 885111-46-6
• Molecular Formula: C₂₃H₂₉NO₅S
• Molecular Weight: 431.553
• Mol file: 885111-46-6.mol

Synonyms:Toluene-4-sulfonic acid 4-((2R,3S)-3-benzyloxy-6-oxo-piperidin-2-yl)-butyl ester

Chemical Property of Toluene-4-sulfonic acid 4-((2R,3S)-3-benzyloxy-6-oxo-piperidin-2-yl)-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid 4-((2R,3S)-3-benzyloxy-6-oxo-piperidin-2-yl)-butyl ester

There total 4 articles about Toluene-4-sulfonic acid 4-((2R,3S)-3-benzyloxy-6-oxo-piperidin-2-yl)-butyl 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: 70.0%

Toluene-4-sulfonic acid 4-[(2R,3S)-3-benzyloxy-1-(4-methoxy-benzyl)-6-oxo-piperidin-2-yl]-butyl ester (885111-45-5) → Toluene-4-sulfonic acid 4-((2R,3S)-3-benzyloxy-6-oxo-piperidin-2-yl)-butyl ester (885111-46-6)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 - 20 ℃;

DOI:10.1021/ol0602203

Reference yield:

(S)-3-benzyloxy-1-(4-methoxybenzyl)-2,6-piperidinedione (763105-88-0) → Toluene-4-sulfonic acid 4-((2R,3S)-3-benzyloxy-6-oxo-piperidin-2-yl)-butyl ester (885111-46-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 3 h / -78 °C

1.2: Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / -78 - 20 °C

2.1: 92 percent / pyridine / CH₂Cl₂ / -30 - -10 °C

3.1: 70 percent / CAN / acetonitrile; H₂O / 0 - 20 °C

With pyridine; ammonium cerium(IV) nitrate; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1021/ol0602203

Reference yield:

(5S,6R)-5-Benzyloxy-6-(4-hydroxy-butyl)-1-(4-methoxy-benzyl)-piperidin-2-one (885111-44-4) → Toluene-4-sulfonic acid 4-((2R,3S)-3-benzyloxy-6-oxo-piperidin-2-yl)-butyl ester (885111-46-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / pyridine / CH₂Cl₂ / -30 - -10 °C

2: 70 percent / CAN / acetonitrile; H₂O / 0 - 20 °C

With pyridine; ammonium cerium(IV) nitrate; In dichloromethane; water; acetonitrile;

DOI:10.1021/ol0602203

upstream raw materials:

Toluene-4-sulfonic acid 4-[(2R,3S)-3-benzyloxy-1-(4-methoxy-benzyl)-6-oxo-piperidin-2-yl]-butyl ester

(S)-3-benzyloxy-1-(4-methoxybenzyl)-2,6-piperidinedione

(5S,6R)-5-Benzyloxy-6-(4-hydroxy-butyl)-1-(4-methoxy-benzyl)-piperidin-2-one

p-toluenesulfonyl chloride

Downstream raw materials:

(1S,9aR)-1-Benzyloxy-octahydro-quinolizin-4-one