(R)-4-chloro-N-[2-(6-chloropyridin-2-yl)-2-hydroxy-3-(tetrahydropyran-2-yloxy)propyl]-3,N-dimethylbenzenesulfonamide

Base Information

Chemical Name:(R)-4-chloro-N-[2-(6-chloropyridin-2-yl)-2-hydroxy-3-(tetrahydropyran-2-yloxy)propyl]-3,N-dimethylbenzenesulfonamide
CAS No.:369377-97-9
Molecular Formula:C₂₁H₂₆Cl₂N₂O₅S
Molecular Weight:489.42
Hs Code.:

Synonyms:(R)-4-chloro-N-[2-(6-chloropyridin-2-yl)-2-hydroxy-3-(tetrahydropyran-2-yloxy)propyl]-3,N-dimethylbenzenesulfonamide

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Chemical Property of (R)-4-chloro-N-[2-(6-chloropyridin-2-yl)-2-hydroxy-3-(tetrahydropyran-2-yloxy)propyl]-3,N-dimethylbenzenesulfonamide

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Technology Process of (R)-4-chloro-N-[2-(6-chloropyridin-2-yl)-2-hydroxy-3-(tetrahydropyran-2-yloxy)propyl]-3,N-dimethylbenzenesulfonamide

There total 7 articles about (R)-4-chloro-N-[2-(6-chloropyridin-2-yl)-2-hydroxy-3-(tetrahydropyran-2-yloxy)propyl]-3,N-dimethylbenzenesulfonamide 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: 64.0%

: 4-chloro-3,N-dimethylbenzenesulfonamide

: 369377-94-6
(S)-2-chloro-6-[2-(tetrahydropyran-2-yloxymethyl)oxiran-2-yl]pyridine

: 369377-97-9
(R)-4-chloro-N-[2-(6-chloropyridin-2-yl)-2-hydroxy-3-(tetrahydropyran-2-yloxy)propyl]-3,N-dimethylbenzenesulfonamide

Guidance literature:: With sodium hydroxide; tetrabutylammomium bromide; In toluene; at 100 ℃; for 3.5h;
DOI:10.1271/bbb.65.1482

Reference yield:

: 110-87-2
3,4-dihydro-2H-pyran

: 369377-97-9
(R)-4-chloro-N-[2-(6-chloropyridin-2-yl)-2-hydroxy-3-(tetrahydropyran-2-yloxy)propyl]-3,N-dimethylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / p-toluenesulfonic acid monohydrate / CH₂Cl₂ / 1.5 h / 20 °C

2: 64 percent / tetra-N-butylammonium bromide; aq. NaOH / toluene / 3.5 h / 100 °C

With sodium hydroxide; tetrabutylammomium bromide; toluene-4-sulfonic acid; In dichloromethane; toluene;
DOI:10.1271/bbb.65.1482

Reference yield:

: 118775-50-1
2-chloro-6-(1-chloromethylvinyl)pyridine

: 369377-97-9
(R)-4-chloro-N-[2-(6-chloropyridin-2-yl)-2-hydroxy-3-(tetrahydropyran-2-yloxy)propyl]-3,N-dimethylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: 35.5 g / HOAc / 24 h / 100 °C

2.1: 90 percent / Et₃N; H₂O / methanol / 3 h / Heating

3.1: Ti(O-i-Pr)2Cl₂; D-(+)-diethyl tartrate / CH₂Cl₂ / 0.33 h / 20 °C

3.2: t-butyl hydroperoxide / CH₂Cl₂ / 48 h / -20 °C

4.1: aq. NaOH / diethyl ether / 0.5 h / 0 - 5 °C

5.1: 70 percent / p-toluenesulfonic acid monohydrate / CH₂Cl₂ / 1.5 h / 20 °C

6.1: 64 percent / tetra-N-butylammonium bromide; aq. NaOH / toluene / 3.5 h / 100 °C

With sodium hydroxide; titanium(IV) dichlorodiisopropylate; D-(+)-diethyl tartrate; tetrabutylammomium bromide; water; toluene-4-sulfonic acid; acetic acid; triethylamine; In methanol; diethyl ether; dichloromethane; toluene; 3.1: Sharpless asymmetric chlorohydroxylation / 3.2: Sharpless asymmetric chlorohydroxylation;
DOI:10.1271/bbb.65.1482