(2S,5S,6S,7R,8R,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl (4-nitrobenzene)sulfonate

Base Information

Chemical Name:(2S,5S,6S,7R,8R,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl (4-nitrobenzene)sulfonate
CAS No.:248948-63-2
Molecular Formula:C₃₄H₃₉N₃O₉S
Molecular Weight:665.764
Hs Code.:

(2S,5S,6S,7R,8R,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl (4-nitrobenzene)sulfonate

Synonyms:(2S,5S,6S,7R,8R,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl (4-nitrobenzene)sulfonate

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Chemical Property of (2S,5S,6S,7R,8R,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl (4-nitrobenzene)sulfonate

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Technology Process of (2S,5S,6S,7R,8R,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl (4-nitrobenzene)sulfonate

There total 12 articles about (2S,5S,6S,7R,8R,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl (4-nitrobenzene)sulfonate 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: 65.0%

: 98-74-8
4-Nitrobenzenesulfonyl chloride

: (2S,5S,6S,7S,8R,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocine-6,8-diol

: 248948-63-2
(2S,5S,6S,7R,8R,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl (4-nitrobenzene)sulfonate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 5h;
DOI:10.1021/ja991160h

Reference yield:

: (S)-2-(11-Hydroxy-10-oxo-1,4-dioxa-9-aza-dispiro[4.2.4.2]tetradec-9-yl)-3-(4-methoxy-phenyl)-propionic acid methyl ester

: 248948-63-2
(2S,5S,6S,7R,8R,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl (4-nitrobenzene)sulfonate

Guidance literature:: Multi-step reaction with 11 steps

1.1: DMAP / CH₂Cl₂ / 12 h / 25 °C

2.1: NaN₃ / dimethylformamide / 12 h / 25 °C

3.1: 90 percent / H₂ / 5 percent Pd/C / ethanol / 760 Torr

4.1: 92 percent / NaH / dimethylformamide / 2 h / 25 °C

5.1: LiBH₄ / diethyl ether / 2 h

6.1: aq. HCl / acetic acid / 12 h

7.1: 95 percent / Et₃N / CH₂Cl₂ / 3 h / 25 °C

8.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 25 °C

9.1: KO-t-Bu / 2-methyl-propan-2-ol / 0.5 h / 25 °C

9.2: TFA / CH₂Cl₂ / 2 h / 25 °C

9.3: LAH / tetrahydrofuran / 2 h / Heating

10.1: 52 percent / Et₃N / CH₂Cl₂ / 25 °C

11.1: 65 percent / Et₃N; DMAP / CH₂Cl₂ / 5 h / 0 °C

With hydrogenchloride; dmap; lithium borohydride; sodium azide; potassium tert-butylate; hydrogen; sodium hydride; Dess-Martin periodane; triethylamine; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Tosylation / 2.1: Substitution / 3.1: Hydrogenolysis / 4.1: Methylation / 5.1: Reduction / 6.1: Hydrolysis / 7.1: Acylation / 8.1: Oxidation / 9.1: Cyclization / 9.2: Hydrolysis / 9.3: Reduction / 10.1: Acylation / 11.1: Condensation;
DOI:10.1021/ja991160h

Reference yield:

: 248948-40-5
methyl (αS,3S)-11-azido-α-[(4-methoxyphenyl)methyl]-10-oxo-1,4-dioxa-9-azadispiro[4.2.4.2]tetradecane-9-acetate

: 248948-63-2
(2S,5S,6S,7R,8R,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl (4-nitrobenzene)sulfonate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 90 percent / H₂ / 5 percent Pd/C / ethanol / 760 Torr

2.1: 92 percent / NaH / dimethylformamide / 2 h / 25 °C

3.1: LiBH₄ / diethyl ether / 2 h

4.1: aq. HCl / acetic acid / 12 h

5.1: 95 percent / Et₃N / CH₂Cl₂ / 3 h / 25 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 25 °C

7.1: KO-t-Bu / 2-methyl-propan-2-ol / 0.5 h / 25 °C

7.2: TFA / CH₂Cl₂ / 2 h / 25 °C

7.3: LAH / tetrahydrofuran / 2 h / Heating

8.1: 52 percent / Et₃N / CH₂Cl₂ / 25 °C

9.1: 65 percent / Et₃N; DMAP / CH₂Cl₂ / 5 h / 0 °C

With hydrogenchloride; dmap; lithium borohydride; potassium tert-butylate; hydrogen; sodium hydride; Dess-Martin periodane; triethylamine; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Hydrogenolysis / 2.1: Methylation / 3.1: Reduction / 4.1: Hydrolysis / 5.1: Acylation / 6.1: Oxidation / 7.1: Cyclization / 7.2: Hydrolysis / 7.3: Reduction / 8.1: Acylation / 9.1: Condensation;
DOI:10.1021/ja991160h