tert-butyl (3aR,5S,6S,7R,7aR)-6,7-bis(benzyloxy)-5-formyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(2-fluoroethyl)carbamate

Base Information

Chemical Name:tert-butyl (3aR,5S,6S,7R,7aR)-6,7-bis(benzyloxy)-5-formyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(2-fluoroethyl)carbamate
CAS No.:1374662-08-4
Molecular Formula:C₂₈H₃₃FN₂O₆S
Molecular Weight:544.644
Hs Code.:

Synonyms:tert-butyl (3aR,5S,6S,7R,7aR)-6,7-bis(benzyloxy)-5-formyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(2-fluoroethyl)carbamate

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

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

There total 11 articles about tert-butyl (3aR,5S,6S,7R,7aR)-6,7-bis(benzyloxy)-5-formyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(2-fluoroethyl)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: 67.0%

: 1374662-07-3
tert-butyl (3aR,5R,6S,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(2-fluoroethyl)carbamate

: 1374662-08-4
tert-butyl (3aR,5S,6S,7R,7aR)-6,7-bis(benzyloxy)-5-formyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(2-fluoroethyl)carbamate

Guidance literature:: With N-Bromosuccinimide; potassium hydrogencarbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide; In dichloromethane; water; at 10 - 15 ℃; for 0.25h;

Reference yield:

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

: 1374662-08-4
tert-butyl (3aR,5S,6S,7R,7aR)-6,7-bis(benzyloxy)-5-formyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(2-fluoroethyl)carbamate

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine / methanol / 20 °C

2.1: triethylamine / dmap / dichloromethane / 6 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 10 °C / Inert atmosphere

3.2: 0.25 h

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

5.1: N-Bromosuccinimide; potassium hydrogencarbonate / tetrabutylammomium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; water / 0.25 h / 10 - 15 °C

With N-Bromosuccinimide; tetrabutyl ammonium fluoride; sodium hydride; potassium hydrogencarbonate; triethylamine; dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

: (3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-2-(2-fluoroethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl diacetate

: 1374662-08-4
tert-butyl (3aR,5S,6S,7R,7aR)-6,7-bis(benzyloxy)-5-formyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(2-fluoroethyl)carbamate

Guidance literature:: Multi-step reaction with 6 steps

1.1: potassium carbonate; methanol / 20 °C

2.1: triethylamine / methanol / 20 °C

3.1: triethylamine / dmap / dichloromethane / 6 h / 20 °C

4.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 10 °C / Inert atmosphere

4.2: 0.25 h

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

6.1: N-Bromosuccinimide; potassium hydrogencarbonate / tetrabutylammomium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; water / 0.25 h / 10 - 15 °C

With methanol; N-Bromosuccinimide; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; potassium hydrogencarbonate; triethylamine; dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;