tert-butyl [(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(hydroxymethyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]carbamate

Base Information

Chemical Name:tert-butyl [(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(hydroxymethyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]carbamate
CAS No.:1425947-64-3
Molecular Formula:C₁₉H₂₄F₂N₂O₄S
Molecular Weight:414.473
Hs Code.:

Synonyms:tert-butyl [(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(hydroxymethyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]carbamate

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Chemical Property of tert-butyl [(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(hydroxymethyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]carbamate

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Technology Process of tert-butyl [(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(hydroxymethyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]carbamate

There total 11 articles about tert-butyl [(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(hydroxymethyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-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: 83.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 1425947-23-4
[(4aR,6R,8aS)-2-amino-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-6-yl]methanol

: 1425947-64-3
tert-butyl [(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(hydroxymethyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]carbamate

Guidance literature:: With triethylamine; In tetrahydrofuran; methanol; at 20 ℃; for 18h;

Reference yield:

: 1425947-61-0
(3aR,5R,7aS)-5-[(benzyloxy)methyl]-7a-(2,4-difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole

: 1425947-64-3
tert-butyl [(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(hydroxymethyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]carbamate

Guidance literature:: Multi-step reaction with 6 steps

1: acetic acid; zinc / 18 h / 20 °C / Inert atmosphere

2: dichloromethane / 18 h / 20 °C / Inert atmosphere

3: hydrogenchloride / methanol / 3 h / 70 °C / Inert atmosphere

4: hydrogenchloride / 3 h / 120 °C / Inert atmosphere

5: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

6: triethylamine / methanol; tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

With piperidine; hydrogenchloride; acetic acid; triethylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm501833t

Reference yield:

: 1425947-62-1
[(2R,4R,5S)-5-amino-2-[(benzyloxy)methyl]-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol

: 1425947-64-3
tert-butyl [(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(hydroxymethyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]carbamate

Guidance literature:: Multi-step reaction with 5 steps

1: dichloromethane / 18 h / 20 °C / Inert atmosphere

2: hydrogenchloride / methanol / 3 h / 70 °C / Inert atmosphere

3: hydrogenchloride / 3 h / 120 °C / Inert atmosphere

4: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

5: triethylamine / methanol; tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

With piperidine; hydrogenchloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm501833t