(4aS,6S,8aR)-1-Allyl-6-(4-chloro-benzenesulfonyl)-6-(2,5-difluoro-phenyl)-octahydro-benzo[c][1,2]thiazine 2,2-dioxide

Base Information

Chemical Name:(4aS,6S,8aR)-1-Allyl-6-(4-chloro-benzenesulfonyl)-6-(2,5-difluoro-phenyl)-octahydro-benzo[c][1,2]thiazine 2,2-dioxide
CAS No.:894853-80-6
Molecular Formula:C₂₃H₂₄ClF₂NO₄S₂
Molecular Weight:516.03
Hs Code.:

Synonyms:(4aS,6S,8aR)-1-Allyl-6-(4-chloro-benzenesulfonyl)-6-(2,5-difluoro-phenyl)-octahydro-benzo[c][1,2]thiazine 2,2-dioxide

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Chemical Property of (4aS,6S,8aR)-1-Allyl-6-(4-chloro-benzenesulfonyl)-6-(2,5-difluoro-phenyl)-octahydro-benzo[c][1,2]thiazine 2,2-dioxide

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Technology Process of (4aS,6S,8aR)-1-Allyl-6-(4-chloro-benzenesulfonyl)-6-(2,5-difluoro-phenyl)-octahydro-benzo[c][1,2]thiazine 2,2-dioxide

There total 10 articles about (4aS,6S,8aR)-1-Allyl-6-(4-chloro-benzenesulfonyl)-6-(2,5-difluoro-phenyl)-octahydro-benzo[c][1,2]thiazine 2,2-dioxide 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: 85.0%

: 894853-79-3
Toluene-4-sulfonic acid (1S,2R,5S)-2-(allyl-methanesulfonyl-amino)-5-(4-chloro-benzenesulfonyl)-5-(2,5-difluoro-phenyl)-cyclohexylmethyl ester

: 894853-80-6
(4aS,6S,8aR)-1-Allyl-6-(4-chloro-benzenesulfonyl)-6-(2,5-difluoro-phenyl)-octahydro-benzo[c][1,2]thiazine 2,2-dioxide

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -30 - 20 ℃;
DOI:10.1016/j.bmcl.2005.12.083

Reference yield:

: 471903-20-5
4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexanone

: 894853-80-6
(4aS,6S,8aR)-1-Allyl-6-(4-chloro-benzenesulfonyl)-6-(2,5-difluoro-phenyl)-octahydro-benzo[c][1,2]thiazine 2,2-dioxide

Guidance literature:: Multi-step reaction with 10 steps

1.1: nBuLi; LiCl; [S-(R*,R*)]-(-)-bis-α-methylbenzylamine / tetrahydrofuran / -100 °C

1.2: 75 percent / SnCl₄ / CH₂Cl₂ / -40 °C

2.1: 80 percent / NaBH₄ / propan-2-ol / -20 °C

3.1: 97 percent / Et₃N / CH₂Cl₂

4.1: 75 percent / NaN₃ / dimethylformamide / 90 °C

5.1: 95 percent / Ph₃P; water / tetrahydrofuran

6.1: 95 percent / Et₃N / CH₂Cl₂

7.1: 70 percent / NaH / dimethylformamide / 70 °C

8.1: 95 percent / BF₃*Et₂O / CH₂Cl₂

9.1: 80 percent / pyridine; DMAP

10.1: 85 percent / nBuLi / tetrahydrofuran / -30 - 20 °C

With pyridine; dmap; sodium tetrahydroborate; n-butyllithium; sodium azide; [S-(R*,R*)]-(-)-bis-α-methylbenzylamine; boron trifluoride diethyl etherate; water; sodium hydride; triethylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1016/j.bmcl.2005.12.083

Reference yield:

: 894853-74-8
(2R,4S)-4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)-2-[2-(trimethylsilyl)ethoxymethyl]cyclohexanone

: 894853-80-6
(4aS,6S,8aR)-1-Allyl-6-(4-chloro-benzenesulfonyl)-6-(2,5-difluoro-phenyl)-octahydro-benzo[c][1,2]thiazine 2,2-dioxide

Guidance literature:: Multi-step reaction with 9 steps

1: 80 percent / NaBH₄ / propan-2-ol / -20 °C

2: 97 percent / Et₃N / CH₂Cl₂

3: 75 percent / NaN₃ / dimethylformamide / 90 °C

4: 95 percent / Ph₃P; water / tetrahydrofuran

5: 95 percent / Et₃N / CH₂Cl₂

6: 70 percent / NaH / dimethylformamide / 70 °C

7: 95 percent / BF₃*Et₂O / CH₂Cl₂

8: 80 percent / pyridine; DMAP

9: 85 percent / nBuLi / tetrahydrofuran / -30 - 20 °C

With pyridine; dmap; sodium tetrahydroborate; n-butyllithium; sodium azide; boron trifluoride diethyl etherate; water; sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1016/j.bmcl.2005.12.083