(2S,3S_.4S,5S)-2,5-Bis(N,N-dibenzylamino)-1,6-diphenyl-3,4-bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyloxy)hexane

Base Information

• Chemical Name: (2S,3S_.4S,5S)-2,5-Bis(N,N-dibenzylamino)-1,6-diphenyl-3,4-bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyloxy)hexane
• CAS No.: 247576-11-0
• Molecular Formula: C₆₂H₇₄N₄O₆
• Molecular Weight: 971.293

Synonyms:(2S,3S_.4S,5S)-2,5-Bis(N,N-dibenzylamino)-1,6-diphenyl-3,4-bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyloxy)hexane

Chemical Property of (2S,3S_.4S,5S)-2,5-Bis(N,N-dibenzylamino)-1,6-diphenyl-3,4-bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyloxy)hexane

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Technology Process of (2S,3S_.4S,5S)-2,5-Bis(N,N-dibenzylamino)-1,6-diphenyl-3,4-bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyloxy)hexane

There total 1 articles about (2S,3S_.4S,5S)-2,5-Bis(N,N-dibenzylamino)-1,6-diphenyl-3,4-bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyloxy)hexane 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: 30.0%

2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (S)-2-dibenzylamino-3-phenyl-propyl ester (247575-73-1) → 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (1S,2S,3S)-3-dibenzylamino-1-((S)-1-dibenzylamino-2-phenyl-ethyl)-2-hydroxy-4-phenyl-butyl ester (247575-76-4) + (2S,3S.4S,5S)-2,5-Bis(N,N-dibenzylamino)-1,6-diphenyl-3,4-bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyloxy)hexane (247576-11-0)

Guidance literature:

2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (S)-2-dibenzylamino-3-phenyl-propyl ester; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; hexane; cyclohexane; at -78 ℃; for 6h;

With copper(ll) bromide; In diethyl ether; hexane; cyclohexane; at -78 - 20 ℃;

With oxygen; In diethyl ether; hexane; cyclohexane; at 20 ℃;

DOI:10.1055/s-1999-3576

Reference yield:

(2S,3S.4S,5S)-2,5-Bis(N,N-dibenzylamino)-1,6-diphenyl-3,4-bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyloxy)hexane (247576-11-0) → (2-Hydroxy-1,1-dimethyl-ethyl)-carbamic acid (1S,2S,3S)-3-dibenzylamino-1-((S)-1-dibenzylamino-2-phenyl-ethyl)-2-(2-hydroxy-1,1-dimethyl-ethylcarbamoyloxy)-4-phenyl-butyl ester

Guidance literature:

With 1.3-propanedithiol; methanesulfonic acid; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1055/s-1999-3576

Reference yield:

(2S,3S.4S,5S)-2,5-Bis(N,N-dibenzylamino)-1,6-diphenyl-3,4-bis(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyloxy)hexane (247576-11-0) → (2S,3S,4S,5S)-2,5-diamino-1,6-diphenyl-3,4-hexanediol (134878-06-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,3-propanedithiol; MeSO₃H / CH₂Cl₂ / 24 h / 20 °C

2: K₂CO₃ / methanol / 24 h / Heating

3: HCO₂H; H₂ / Pd/C / methanol / 48 h / 20 °C

With 1.3-propanedithiol; formic acid; methanesulfonic acid; hydrogen; potassium carbonate; palladium on activated charcoal; In methanol; dichloromethane; 1: Ring cleavage / 2: Hydrolysis / 3: Hydrogenolysis;

DOI:10.1055/s-1999-3576

upstream raw materials:

2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (S)-2-dibenzylamino-3-phenyl-propyl ester

Downstream raw materials:

(2S,3S,4S,5S)-2,5-diamino-1,6-diphenyl-3,4-hexanediol

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