(3aR,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-N,N-dimethyl-5-(2,2,2-trifluoroethyl)-5,6,7,7a tetrahydro-3aH-pyrano[3,2-d]thiazol-2-amine

Base Information

Chemical Name:(3aR,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-N,N-dimethyl-5-(2,2,2-trifluoroethyl)-5,6,7,7a tetrahydro-3aH-pyrano[3,2-d]thiazol-2-amine
CAS No.:1374768-50-9
Molecular Formula:C₂₄H₂₇F₃N₂O₃S
Molecular Weight:480.551
Hs Code.:

Synonyms:(3aR,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-N,N-dimethyl-5-(2,2,2-trifluoroethyl)-5,6,7,7a tetrahydro-3aH-pyrano[3,2-d]thiazol-2-amine

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Chemical Property of (3aR,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-N,N-dimethyl-5-(2,2,2-trifluoroethyl)-5,6,7,7a tetrahydro-3aH-pyrano[3,2-d]thiazol-2-amine

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Technology Process of (3aR,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-N,N-dimethyl-5-(2,2,2-trifluoroethyl)-5,6,7,7a tetrahydro-3aH-pyrano[3,2-d]thiazol-2-amine

There total 10 articles about (3aR,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-N,N-dimethyl-5-(2,2,2-trifluoroethyl)-5,6,7,7a tetrahydro-3aH-pyrano[3,2-d]thiazol-2-amine 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: 87.0%

: O-1-((3aR,5S,6S,7R,7aR)-6,7-bis(benzyloxy)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)-2,2,2-trifluoroethyl S-methylcarbonodithioate

: 1374768-50-9
(3aR,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-N,N-dimethyl-5-(2,2,2-trifluoroethyl)-5,6,7,7a tetrahydro-3aH-pyrano[3,2-d]thiazol-2-amine

Guidance literature:: With tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile); In toluene; at 100 ℃; for 1h;

Reference yield:

: 191281-31-9
(3aR,5R,6S,7R,7aR)-(5-(acetoxymethyl)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl)diacetate

: 1374768-50-9
(3aR,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-N,N-dimethyl-5-(2,2,2-trifluoroethyl)-5,6,7,7a tetrahydro-3aH-pyrano[3,2-d]thiazol-2-amine

Guidance literature:: Multi-step reaction with 8 steps

1.1: potassium carbonate; methanol / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

2.2: 2 h / 20 °C

3.1: zinc(II) chloride; acetic acid / 2 h / 0 - 20 °C

4.1: potassium carbonate; methanol / 8 h / 30 °C

5.1: oxalyl dichloride / dimethyl sulfoxide / dichloromethane / 4 h / -20 °C

5.2: 1 h / -78 - -50 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / -30 - 20 °C / Molecular sieve

7.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 5 °C

8.1: tri-n-butyl-tin hydride / 2,2'-azobis(isobutyronitrile) / toluene / 1 h / 100 °C

With methanol; oxalyl dichloride; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; potassium carbonate; acetic acid; zinc(II) chloride; 2,2'-azobis(isobutyronitrile); dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;

Reference yield:

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

: 1374768-50-9
(3aR,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-N,N-dimethyl-5-(2,2,2-trifluoroethyl)-5,6,7,7a tetrahydro-3aH-pyrano[3,2-d]thiazol-2-amine

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

1.2: 2 h / 20 °C

2.1: zinc(II) chloride; acetic acid / 2 h / 0 - 20 °C

3.1: potassium carbonate; methanol / 8 h / 30 °C

4.1: oxalyl dichloride / dimethyl sulfoxide / dichloromethane / 4 h / -20 °C

4.2: 1 h / -78 - -50 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / -30 - 20 °C / Molecular sieve

6.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 5 °C

7.1: tri-n-butyl-tin hydride / 2,2'-azobis(isobutyronitrile) / toluene / 1 h / 100 °C

With methanol; oxalyl dichloride; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; potassium carbonate; acetic acid; zinc(II) chloride; 2,2'-azobis(isobutyronitrile); dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;