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

Base Information

• Chemical Name: 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
• CAS No.: 1415208-88-6
• Molecular Formula: C₁₇H₂₀BrFN₂O₃S
• Molecular Weight: 431.326
• Mol file: 1415208-88-6.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 2 articles about 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 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: 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;

Reference yield:

(+/-)-(4aR,7aR)-7a-(5-bromo-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-amine → 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:

Multi-step reaction with 2 steps

1: Resolution of racemate; chiral HPLC

2: sodium hydrogencarbonate / 1,4-dioxane; water / 12 h / 20 °C

With sodium hydrogencarbonate; In 1,4-dioxane; water;

Reference yield: 36.5%

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) → 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 (1415208-89-7)

Guidance literature:

With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate; In ethanol; water; at 80 ℃; for 1h;

upstream raw materials:

di-tert-butyl dicarbonate

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

Downstream raw materials:

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

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

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