(+)-(2S,3R)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate

Base Information

• Chemical Name: (+)-(2S,3R)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate
• CAS No.: 1185729-94-5
• Molecular Formula: C₂₄H₂₅N₃O₅
• Molecular Weight: 435.48
• Mol file: 1185729-94-5.mol

Synonyms:(+)-(2S,3R)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate

Chemical Property of (+)-(2S,3R)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2S,3R)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate

There total 4 articles about (+)-(2S,3R)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate 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:

4-Hydroxyquinazoline (491-36-1) + C19H28BrNO4Si → (+)-(2S,3R)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate (1185729-94-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1016/j.tet.2017.07.041

Reference yield:

(2S,5R,6S)-5-hydroxy-6-[2-(4-oxo-4H-quinazolin-3-ylmethyl)-allyl]piperdine-1-carboxylic acid benzyl ester (1185729-93-4) → (+)-(2S,3R)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate (1185729-94-5)

Guidance literature:

With sodium periodate; osmium(VIII) oxide; In tetrahydrofuran; water; for 2h;

DOI:10.1039/b901670h

Reference yield:

(2S,3R)-3-hydroxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester (1203455-33-7) → (+)-(2S,3R)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate (1185729-94-5)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 h / 0 °C / Inert atmosphere

2: N-Bromosuccinimide / dichloromethane / 0.33 h / 0 - 20 °C / Inert atmosphere

3: potassium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C

With N-Bromosuccinimide; potassium carbonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2017.07.041

upstream raw materials:

(2S,5R,6S)-5-hydroxy-6-[2-(4-oxo-4H-quinazolin-3-ylmethyl)-allyl]piperdine-1-carboxylic acid benzyl ester

(2S,3R)-3-hydroxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester

4-Hydroxyquinazoline

(E)-benzyl (4-hydroxy-7-oxooct-5-en-1-yl)carbamate

Downstream raw materials:

febrifugine dihydrochloride