(4R,5S)-7-Benzyloxy-9-(4-methoxy-phenoxymethyl)-4-phenylsulfanyl-1,2,3,4,5,6-hexahydro-benzo[b]azocin-5-ol

Base Information

Chemical Name:(4R,5S)-7-Benzyloxy-9-(4-methoxy-phenoxymethyl)-4-phenylsulfanyl-1,2,3,4,5,6-hexahydro-benzo[b]azocin-5-ol
CAS No.:137964-88-6
Molecular Formula:C₃₂H₃₃NO₄S
Molecular Weight:527.684
Hs Code.:

Synonyms:(4R,5S)-7-Benzyloxy-9-(4-methoxy-phenoxymethyl)-4-phenylsulfanyl-1,2,3,4,5,6-hexahydro-benzo[b]azocin-5-ol

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Chemical Property of (4R,5S)-7-Benzyloxy-9-(4-methoxy-phenoxymethyl)-4-phenylsulfanyl-1,2,3,4,5,6-hexahydro-benzo[b]azocin-5-ol

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Technology Process of (4R,5S)-7-Benzyloxy-9-(4-methoxy-phenoxymethyl)-4-phenylsulfanyl-1,2,3,4,5,6-hexahydro-benzo[b]azocin-5-ol

There total 16 articles about (4R,5S)-7-Benzyloxy-9-(4-methoxy-phenoxymethyl)-4-phenylsulfanyl-1,2,3,4,5,6-hexahydro-benzo[b]azocin-5-ol 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:

: 137964-81-9
2-Benzylamino-6-hydroxy-4-methyl-benzoic acid ethyl ester

: 137964-88-6
(4R,5S)-7-Benzyloxy-9-(4-methoxy-phenoxymethyl)-4-phenylsulfanyl-1,2,3,4,5,6-hexahydro-benzo[b]azocin-5-ol

Guidance literature:: Multi-step reaction with 15 steps

1: H₂ / Pd/C / ethanol / 2 h / 23 °C / 62057.8 Torr

2: 1.) aq. NaNO₂, HCl, 2.) NaN₃ / 1.) EtOH, 0 deg C, 20 min, 2.) EtOH, 0 deg C, 40 min

3: i-Pr₂NEt / CH₂Cl₂ / 23 °C

4: NBS, Bz₂O₂ / benzene / 2 h / Heating

5: K₂CO₃ / dimethylformamide / 0.25 h / 70 °C

6: TFA / CH₂Cl₂ / 3 h / 23 °C

7: K₂CO₃ / dimethylformamide / 80 °C

8: 100 percent / DIBAL / CH₂Cl₂ / -78 °C

9: 98 percent / PCC / CH₂Cl₂ / 23 °C

10: 1.) SnCl₄, 2.) aq. HCl / 1.) CH₂Cl₂, -78 deg C, 5 min, 2.) THF, 23 deg C

11: Et₃N / CH₂Cl₂ / 0.5 h / 23 °C

12: pyridine / 2 h / 23 °C

13: Et₃SiH, BF₃*Et₂O / CH₂Cl₂ / 23 °C

14: Zn, AcOH / diethyl ether; CH₂Cl₂ / 23 °C

15: 1.) DIBAL, 2.) NaBH₃CN, TFA / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, CH₃OH, 23 deg C, 10 min

With pyridine; hydrogenchloride; triethylsilane; N-Bromosuccinimide; sodium azide; boron trifluoride diethyl etherate; hydrogen; tin(IV) chloride; diisobutylaluminium hydride; sodium cyanoborohydride; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; trifluoroacetic acid; zinc; sodium nitrite; dibenzoyl peroxide; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00027a071

Reference yield:

: 100-44-7
benzyl chloride

: 137964-88-6
(4R,5S)-7-Benzyloxy-9-(4-methoxy-phenoxymethyl)-4-phenylsulfanyl-1,2,3,4,5,6-hexahydro-benzo[b]azocin-5-ol

Guidance literature:: Multi-step reaction with 9 steps

1: K₂CO₃ / dimethylformamide / 80 °C

2: 100 percent / DIBAL / CH₂Cl₂ / -78 °C

3: 98 percent / PCC / CH₂Cl₂ / 23 °C

4: 1.) SnCl₄, 2.) aq. HCl / 1.) CH₂Cl₂, -78 deg C, 5 min, 2.) THF, 23 deg C

5: Et₃N / CH₂Cl₂ / 0.5 h / 23 °C

6: pyridine / 2 h / 23 °C

7: Et₃SiH, BF₃*Et₂O / CH₂Cl₂ / 23 °C

8: Zn, AcOH / diethyl ether; CH₂Cl₂ / 23 °C

9: 1.) DIBAL, 2.) NaBH₃CN, TFA / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, CH₃OH, 23 deg C, 10 min

With pyridine; hydrogenchloride; triethylsilane; boron trifluoride diethyl etherate; tin(IV) chloride; diisobutylaluminium hydride; sodium cyanoborohydride; potassium carbonate; acetic acid; triethylamine; pyridinium chlorochromate; trifluoroacetic acid; zinc; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00027a071

Reference yield:

: 2-Amino-6-hydroxy-4-methyl-benzoic acid ethyl ester

: 137964-88-6
(4R,5S)-7-Benzyloxy-9-(4-methoxy-phenoxymethyl)-4-phenylsulfanyl-1,2,3,4,5,6-hexahydro-benzo[b]azocin-5-ol

Guidance literature:: Multi-step reaction with 14 steps

1: 1.) aq. NaNO₂, HCl, 2.) NaN₃ / 1.) EtOH, 0 deg C, 20 min, 2.) EtOH, 0 deg C, 40 min

2: i-Pr₂NEt / CH₂Cl₂ / 23 °C

3: NBS, Bz₂O₂ / benzene / 2 h / Heating

4: K₂CO₃ / dimethylformamide / 0.25 h / 70 °C

5: TFA / CH₂Cl₂ / 3 h / 23 °C

6: K₂CO₃ / dimethylformamide / 80 °C

7: 100 percent / DIBAL / CH₂Cl₂ / -78 °C

8: 98 percent / PCC / CH₂Cl₂ / 23 °C

9: 1.) SnCl₄, 2.) aq. HCl / 1.) CH₂Cl₂, -78 deg C, 5 min, 2.) THF, 23 deg C

10: Et₃N / CH₂Cl₂ / 0.5 h / 23 °C

11: pyridine / 2 h / 23 °C

12: Et₃SiH, BF₃*Et₂O / CH₂Cl₂ / 23 °C

13: Zn, AcOH / diethyl ether; CH₂Cl₂ / 23 °C

14: 1.) DIBAL, 2.) NaBH₃CN, TFA / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, CH₃OH, 23 deg C, 10 min

With pyridine; hydrogenchloride; triethylsilane; N-Bromosuccinimide; sodium azide; boron trifluoride diethyl etherate; tin(IV) chloride; diisobutylaluminium hydride; sodium cyanoborohydride; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; trifluoroacetic acid; zinc; sodium nitrite; dibenzoyl peroxide; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00027a071