N-Benzyl-N-((E)-(2R,3S)-2,3-bis-benzyloxy-6-hydroxy-hex-4-enyl)-4-methyl-benzenesulfonamide

Base Information

Chemical Name:N-Benzyl-N-((E)-(2R,3S)-2,3-bis-benzyloxy-6-hydroxy-hex-4-enyl)-4-methyl-benzenesulfonamide
CAS No.:94349-12-9
Molecular Formula:C₃₄H₃₇NO₅S
Molecular Weight:571.737
Hs Code.:

Synonyms:N-Benzyl-N-((E)-(2R,3S)-2,3-bis-benzyloxy-6-hydroxy-hex-4-enyl)-4-methyl-benzenesulfonamide

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Chemical Property of N-Benzyl-N-((E)-(2R,3S)-2,3-bis-benzyloxy-6-hydroxy-hex-4-enyl)-4-methyl-benzenesulfonamide

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Technology Process of N-Benzyl-N-((E)-(2R,3S)-2,3-bis-benzyloxy-6-hydroxy-hex-4-enyl)-4-methyl-benzenesulfonamide

There total 12 articles about N-Benzyl-N-((E)-(2R,3S)-2,3-bis-benzyloxy-6-hydroxy-hex-4-enyl)-4-methyl-benzenesulfonamide 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: 93.0%

: 94349-10-7
(E)-(4S,5R)-4,5-Bis-benzyloxy-6-[benzyl-(toluene-4-sulfonyl)-amino]-hex-2-enoic acid ethyl ester

: 94349-12-9
N-Benzyl-N-((E)-(2R,3S)-2,3-bis-benzyloxy-6-hydroxy-hex-4-enyl)-4-methyl-benzenesulfonamide

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃; for 1h;
DOI:10.1021/jo00203a039

Reference yield:

: 1576-37-0
N-benzyl-p-toluenesulfonamide

: 94349-12-9
N-Benzyl-N-((E)-(2R,3S)-2,3-bis-benzyloxy-6-hydroxy-hex-4-enyl)-4-methyl-benzenesulfonamide

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) NaH / 1.) DMF, 2.) DMF, from 0 deg C to RT, 6 h

2: dimethylformamide / 5 h / 120 °C

3: K₂CO₃ / methanol / 2 h / Ambient temperature

4: 91 percent / (-)-Dipt, Ti(O-i-Pr)4, TBHP / CH₂Cl₂ / 2.5 h / -20 °C

5: 71 percent / 0.5 N aq. NaOH / 2-methyl-propan-2-ol / 5 h / 85 °C

6: 91 percent / NaH, n-Bu₄NI / tetrahydrofuran / 18 h / Ambient temperature

7: 100 percent / MCPBA / CH₂Cl₂ / 2 h / -78 °C

8: 71 percent / (CF₃CO)2O, 2,6-lutidine / 3 h / Ambient temperature

9: 92 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

10: (COCl)2, Me₂SO, DBU / CH₂Cl₂ / 0.5 h / -60 °C

11: NaH / toluene / 0 - 20 °C

12: 93 percent / Dibal / toluene / 1 h / -78 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1021/jo00203a039

Reference yield:

: 94348-98-8
N-Benzyl-N-((E)-4-chloro-but-2-enyl)-4-methyl-benzenesulfonamide

: 94349-12-9
N-Benzyl-N-((E)-(2R,3S)-2,3-bis-benzyloxy-6-hydroxy-hex-4-enyl)-4-methyl-benzenesulfonamide

Guidance literature:: Multi-step reaction with 11 steps

1: dimethylformamide / 5 h / 120 °C

2: K₂CO₃ / methanol / 2 h / Ambient temperature

3: 91 percent / (-)-Dipt, Ti(O-i-Pr)4, TBHP / CH₂Cl₂ / 2.5 h / -20 °C

4: 71 percent / 0.5 N aq. NaOH / 2-methyl-propan-2-ol / 5 h / 85 °C

5: 91 percent / NaH, n-Bu₄NI / tetrahydrofuran / 18 h / Ambient temperature

6: 100 percent / MCPBA / CH₂Cl₂ / 2 h / -78 °C

7: 71 percent / (CF₃CO)2O, 2,6-lutidine / 3 h / Ambient temperature

8: 92 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

9: (COCl)2, Me₂SO, DBU / CH₂Cl₂ / 0.5 h / -60 °C

10: NaH / toluene / 0 - 20 °C

11: 93 percent / Dibal / toluene / 1 h / -78 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1021/jo00203a039