tert-butyl ((3aR,5R,6R,7R,7aR)-6-(benzyloxy)-7-fluoro-5-((S)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(ethyl)carbamate

Base Information

Chemical Name:tert-butyl ((3aR,5R,6R,7R,7aR)-6-(benzyloxy)-7-fluoro-5-((S)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(ethyl)carbamate
CAS No.:1416709-84-6
Molecular Formula:C₂₂H₃₁FN₂O₅S
Molecular Weight:454.563
Hs Code.:

Synonyms:tert-butyl ((3aR,5R,6R,7R,7aR)-6-(benzyloxy)-7-fluoro-5-((S)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(ethyl)carbamate

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Chemical Property of tert-butyl ((3aR,5R,6R,7R,7aR)-6-(benzyloxy)-7-fluoro-5-((S)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(ethyl)carbamate

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Technology Process of tert-butyl ((3aR,5R,6R,7R,7aR)-6-(benzyloxy)-7-fluoro-5-((S)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(ethyl)carbamate

There total 11 articles about tert-butyl ((3aR,5R,6R,7R,7aR)-6-(benzyloxy)-7-fluoro-5-((S)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(ethyl)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:

: 1416709-82-4
tert-butyl ((3aR,5S,6R,7R,7aR)-6-(benzyloxy)-7-fluoro-5-formyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(ethyl)carbamate

: 75-16-1
methylmagnesium bromide

: 1416709-86-8
tert-butyl ((3aR,5R,6R,7R,7aR)-6-(benzyloxy)-7-fluoro-5-((R)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(ethyl)carbamate

: 1416709-84-6
tert-butyl ((3aR,5R,6R,7R,7aR)-6-(benzyloxy)-7-fluoro-5-((S)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(ethyl)carbamate

Guidance literature:: In tetrahydrofuran; toluene; at 20 ℃; for 2h; Overall yield = 60 %; Overall yield = 0.22 g; Optical yield = 37.5 %de; Inert atmosphere;

Reference yield:

: 1009816-48-1
(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol

: 1416709-86-8
tert-butyl ((3aR,5R,6R,7R,7aR)-6-(benzyloxy)-7-fluoro-5-((R)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(ethyl)carbamate

: 1416709-84-6
tert-butyl ((3aR,5R,6R,7R,7aR)-6-(benzyloxy)-7-fluoro-5-((S)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(ethyl)carbamate

Guidance literature:: Multi-step reaction with 9 steps

1: triethylamine / methanol / 10 h / 25 °C

2: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0 - 20 °C

3: diethylamino-sulfur trifluoride / dichloromethane / 48 h / -78 - 20 °C / Inert atmosphere

4: potassium carbonate; methanol / 3 h / 0 - 20 °C

5: 1H-imidazole / N,N-dimethyl-formamide / 72 h / 20 °C

6: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 16 h / 0 - 20 °C

7: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C

8: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C

9: tetrahydrofuran; toluene / 2 h / 20 °C / Inert atmosphere

With 1H-imidazole; methanol; dmap; diethylamino-sulfur trifluoride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;

Reference yield:

: 1382799-64-5
tert-butyl [(3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-2-yl]ethylcarbamate

: 1416709-86-8
tert-butyl ((3aR,5R,6R,7R,7aR)-6-(benzyloxy)-7-fluoro-5-((R)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(ethyl)carbamate

: 1416709-84-6
tert-butyl ((3aR,5R,6R,7R,7aR)-6-(benzyloxy)-7-fluoro-5-((S)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(ethyl)carbamate

Guidance literature:: Multi-step reaction with 8 steps

1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0 - 20 °C

2: diethylamino-sulfur trifluoride / dichloromethane / 48 h / -78 - 20 °C / Inert atmosphere

3: potassium carbonate; methanol / 3 h / 0 - 20 °C

4: 1H-imidazole / N,N-dimethyl-formamide / 72 h / 20 °C

5: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 16 h / 0 - 20 °C

6: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C

7: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C

8: tetrahydrofuran; toluene / 2 h / 20 °C / Inert atmosphere

With 1H-imidazole; methanol; dmap; diethylamino-sulfur trifluoride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;