(1S,3S,4S,5R)-3-[4-amino-3-fluoro-5-(2,2,2-trifluoro-ethoxy)-benzyl]-5-(3-tert-butyl-benzylamino)-1-oxo-tetrahydro-thiopyran-4-ol (trans-sulfoxide)

Base Information

Chemical Name:(1S,3S,4S,5R)-3-[4-amino-3-fluoro-5-(2,2,2-trifluoro-ethoxy)-benzyl]-5-(3-tert-butyl-benzylamino)-1-oxo-tetrahydro-thiopyran-4-ol (trans-sulfoxide)
CAS No.:1123173-31-8
Molecular Formula:C₂₅H₃₂F₄N₂O₃S
Molecular Weight:516.6
Hs Code.:

Synonyms:(1S,3S,4S,5R)-3-[4-amino-3-fluoro-5-(2,2,2-trifluoro-ethoxy)-benzyl]-5-(3-tert-butyl-benzylamino)-1-oxo-tetrahydro-thiopyran-4-ol (trans-sulfoxide)

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Chemical Property of (1S,3S,4S,5R)-3-[4-amino-3-fluoro-5-(2,2,2-trifluoro-ethoxy)-benzyl]-5-(3-tert-butyl-benzylamino)-1-oxo-tetrahydro-thiopyran-4-ol (trans-sulfoxide)

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Technology Process of (1S,3S,4S,5R)-3-[4-amino-3-fluoro-5-(2,2,2-trifluoro-ethoxy)-benzyl]-5-(3-tert-butyl-benzylamino)-1-oxo-tetrahydro-thiopyran-4-ol (trans-sulfoxide)

There total 7 articles about (1S,3S,4S,5R)-3-[4-amino-3-fluoro-5-(2,2,2-trifluoro-ethoxy)-benzyl]-5-(3-tert-butyl-benzylamino)-1-oxo-tetrahydro-thiopyran-4-ol (trans-sulfoxide) 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:

: 1123173-38-5
(1S,3R,4S,5S)-3-(3-tert-butyl-benzylamino)-5-[3-fluoro-4-nitro-5-(2,2,2-trifluoro-ethoxy)-benzyl]-1-oxo-tetrahydro-thiopyran-4-ol

: 1123173-31-8
(1S,3S,4S,5R)-3-[4-amino-3-fluoro-5-(2,2,2-trifluoro-ethoxy)-benzyl]-5-(3-tert-butyl-benzylamino)-1-oxo-tetrahydro-thiopyran-4-ol (trans-sulfoxide)

Guidance literature:: With hydrogen; palladium 10% on activated carbon; In methanol; at 45 ℃; for 4h;

Reference yield:

: 1123172-99-5
((3R,4S,5S)-5-(3,5-difluoro-4-nitrobenzyl)-4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-3-yl)carbamate

: 1123173-31-8
(1S,3S,4S,5R)-3-[4-amino-3-fluoro-5-(2,2,2-trifluoro-ethoxy)-benzyl]-5-(3-tert-butyl-benzylamino)-1-oxo-tetrahydro-thiopyran-4-ol (trans-sulfoxide)

Guidance literature:: Multi-step reaction with 6 steps

1: potassium hexamethylsilazane / tetrahydrofuran / 24 h / 25 °C

2: dihydrogen peroxide / tetrahydrofuran; acetic acid / 6 h / 25 °C

3: trifluoroacetic acid / dichloromethane / 1 h / 25 °C

4: sodium acetate / dichloromethane; methanol / 2 h / 25 °C

5: sodium cyanoborohydride / methanol / 1 h / 25 °C

6: hydrogen; palladium 10% on activated carbon / methanol / 45 °C

With palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; sodium acetate; potassium hexamethylsilazane; sodium cyanoborohydride; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; acetic acid;
DOI:10.1016/j.bmcl.2013.07.071

Reference yield:

: 1123173-46-5
{(1S,3R,4S,5S)-5-[3-fluoro-4-nitro-5-(2,2,2-trifluoro-ethoxy)-benzyl]-4-hydroxy-1-oxo-tetrahydro-thiopyran-3-yl}-carbamic acid tert-butyl ester

: 1123173-31-8
(1S,3S,4S,5R)-3-[4-amino-3-fluoro-5-(2,2,2-trifluoro-ethoxy)-benzyl]-5-(3-tert-butyl-benzylamino)-1-oxo-tetrahydro-thiopyran-4-ol (trans-sulfoxide)

Guidance literature:: Multi-step reaction with 4 steps

1: trifluoroacetic acid / dichloromethane / 1 h / 25 °C

2: sodium acetate / dichloromethane; methanol / 2 h / 25 °C

3: sodium cyanoborohydride / methanol / 1 h / 25 °C

4: hydrogen; palladium 10% on activated carbon / methanol / 45 °C

With palladium 10% on activated carbon; hydrogen; sodium acetate; sodium cyanoborohydride; trifluoroacetic acid; In methanol; dichloromethane;
DOI:10.1016/j.bmcl.2013.07.071