(2'R,4S)-5-[1'-(toluene-4-sulfonyl)-1',2',3',6'-tetrahydropyridin-2'-yl]pentane-1,2,4-triol

Base Information

Chemical Name:(2'R,4S)-5-[1'-(toluene-4-sulfonyl)-1',2',3',6'-tetrahydropyridin-2'-yl]pentane-1,2,4-triol
CAS No.:756821-42-8
Molecular Formula:C₁₇H₂₅NO₅S
Molecular Weight:355.455
Hs Code.:

Synonyms:(2'R,4S)-5-[1'-(toluene-4-sulfonyl)-1',2',3',6'-tetrahydropyridin-2'-yl]pentane-1,2,4-triol

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Chemical Property of (2'R,4S)-5-[1'-(toluene-4-sulfonyl)-1',2',3',6'-tetrahydropyridin-2'-yl]pentane-1,2,4-triol

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Technology Process of (2'R,4S)-5-[1'-(toluene-4-sulfonyl)-1',2',3',6'-tetrahydropyridin-2'-yl]pentane-1,2,4-triol

There total 8 articles about (2'R,4S)-5-[1'-(toluene-4-sulfonyl)-1',2',3',6'-tetrahydropyridin-2'-yl]pentane-1,2,4-triol 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: 60.0%

: 756821-40-6
(2R,2'R)-1-[1'-(toluene-4-sulfonyl)-1',2',3',6'-tetrahydropyridin-2'-yl]pent-4-en-2-ol

: 756821-42-8
(2'R,4S)-5-[1'-(toluene-4-sulfonyl)-1',2',3',6'-tetrahydropyridin-2'-yl]pentane-1,2,4-triol

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; at 0 - 20 ℃;
DOI:10.1016/j.tet.2004.06.051

Reference yield:

: 18303-04-3
N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide

: 756821-42-8
(2'R,4S)-5-[1'-(toluene-4-sulfonyl)-1',2',3',6'-tetrahydropyridin-2'-yl]pentane-1,2,4-triol

Guidance literature:: Multi-step reaction with 7 steps

1: 50 percent / PPh₃; DEAD / tetrahydrofuran / 2 h / 20 °C

2: TFA / CH₂Cl₂ / 0.5 h

3: 290 mg / Et₃N / CH₂Cl₂ / 12 h

4: 85 percent / NaH / dimethylformamide / 1 h / 20 °C

5: 82 percent / Grubbs ruthenium-based catalyst 2nd generation / CH₂Cl₂ / 2 h

6: 98 percent / NaOH / methanol; H₂O / 10 h / 45 °C

7: 60 percent / OsO₄; N-methylmorpholine-N-oxide / H₂O / 0 - 20 °C

With sodium hydroxide; osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Mitsunobu reaction;
DOI:10.1016/j.tet.2004.06.051

Reference yield:

: (1R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohept-3-enol

: 756821-42-8
(2'R,4S)-5-[1'-(toluene-4-sulfonyl)-1',2',3',6'-tetrahydropyridin-2'-yl]pentane-1,2,4-triol

Guidance literature:: Multi-step reaction with 7 steps

1: 50 percent / PPh₃; DEAD / tetrahydrofuran / 2 h / 20 °C

2: TFA / CH₂Cl₂ / 0.5 h

3: 290 mg / Et₃N / CH₂Cl₂ / 12 h

4: 85 percent / NaH / dimethylformamide / 1 h / 20 °C

5: 82 percent / Grubbs ruthenium-based catalyst 2nd generation / CH₂Cl₂ / 2 h

6: 98 percent / NaOH / methanol; H₂O / 10 h / 45 °C

7: 60 percent / OsO₄; N-methylmorpholine-N-oxide / H₂O / 0 - 20 °C

With sodium hydroxide; osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Mitsunobu reaction;
DOI:10.1016/j.tet.2004.06.051