(R,R)-tert-butyl 7a-(2-fluoro-5-bromophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate

Base Information

• Chemical Name: (R,R)-tert-butyl 7a-(2-fluoro-5-bromophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate
• CAS No.: 1415208-86-4
• Molecular Formula: C₁₂H₁₂BrFN₂OS
• Molecular Weight: 331.208
• Mol file: 1415208-86-4.mol

Synonyms:(R,R)-tert-butyl 7a-(2-fluoro-5-bromophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate

Chemical Property of (R,R)-tert-butyl 7a-(2-fluoro-5-bromophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,R)-tert-butyl 7a-(2-fluoro-5-bromophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate

There total 2 articles about (R,R)-tert-butyl 7a-(2-fluoro-5-bromophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate 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:

C18H28BrFN2O2SSi → (R,R)-tert-butyl 7a-(2-fluoro-5-bromophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate (1415208-86-4) + (S,S)-tert-butyl 7a-(2-fluoro-5-bromophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 70 ℃; for 6h;

DOI:10.1021/acs.joc.5b02705

Reference yield:

1-(5-bromo-2-fluorophenyl)-4-((tert-butyldimethylsilyl)oxy)-2-methylenebutan-1-ol → (R,R)-tert-butyl 7a-(2-fluoro-5-bromophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate (1415208-86-4) + (S,S)-tert-butyl 7a-(2-fluoro-5-bromophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate

Guidance literature:

Multi-step reaction with 3 steps

1: manganese(IV) oxide / chloroform / 12 h / Reflux

2: acetic acid / 12 h / 20 °C / Inert atmosphere

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 70 °C

With manganese(IV) oxide; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; chloroform;

DOI:10.1021/acs.joc.5b02705

Reference yield: 56.0%

di-tert-butyl dicarbonate (24424-99-5) + (R,R)-tert-butyl 7a-(2-fluoro-5-bromophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate (1415208-86-4) → tert-butyl ((4aR,7aR)-7a-(5-bromo-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate (1415208-88-6)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 20 ℃; for 12h;

Downstream raw materials:

tert-butyl ((4aR,7aR)-7a-(5-bromo-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate

tert-butyl ((4aR,7aR)-7a-(5-azido-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate

tert-butyl ((4aR,7aR)-7a-(5-amino-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate