(3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester
• CAS No.: 176108-67-1
• Molecular Formula: C₂₅H₃₈N₂O₇S
• Molecular Weight: 510.652
• Mol file: 176108-67-1.mol

Synonyms:(3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester

Chemical Property of (3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester

There total 12 articles about (3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine-5-carboxylic acid tert-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: 97.0%

di-tert-butyl dicarbonate (24424-99-5) + (3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine (397883-99-7) → (3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester (176108-67-1)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 33h;

DOI:10.1021/ol010221p

Reference yield: 73.0%

(3aR,6S,7aS)-2,2-Dimethyl-6-phenylsulfanylmethyl-tetrahydro-oxazolo[4,5-c]pyridine-3,5-dicarboxylic acid di-tert-butyl ester (176108-66-0) → (3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester (176108-67-1)

Guidance literature:

With diphenyl diselenide; dihydrogen peroxide; In diethyl ether; dichloromethane; at 0 - 20 ℃; for 7h;

DOI:10.1016/0040-4020(96)00137-8

Reference yield:

(4S,5R)-5-tert-butoxycarbonylamino-4-hydroxy-2-oxo-piperidine (317819-12-8) → (3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester (176108-67-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 95 percent / TsOH / acetone / 40 h / 20 °C

2.1: nBuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

2.2: 75 percent / tetrahydrofuran; hexane / 0.42 h / -78 °C

3.1: 41 percent / tetrahydrofuran / 0.75 h / -76 °C

4.1: 76 percent / H₂ / Pd(OH)2 / methanol / 50 h / 760.05 Torr

5.1: 97 percent / NaHCO₃ / tetrahydrofuran; H₂O / 33 h / 20 °C

With n-butyllithium; hydrogen; sodium hydrogencarbonate; toluene-4-sulfonic acid; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; water; acetone;

DOI:10.1021/ol010221p

upstream raw materials:

(3aR,6S,7aS)-2,2-Dimethyl-6-phenylsulfanylmethyl-tetrahydro-oxazolo[4,5-c]pyridine-3,5-dicarboxylic acid di-tert-butyl ester

di-tert-butyl dicarbonate

(3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine

(4S,5R)-5-tert-butoxycarbonylamino-4-hydroxy-2-oxo-piperidine