(S_S,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine benzyl ester

Base Information

• Chemical Name: (S_S,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine benzyl ester
• CAS No.: 878395-96-1
• Molecular Formula: C₂₅H₃₃NO₆S
• Molecular Weight: 475.606

Synonyms:(S_S,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine benzyl ester

Chemical Property of (S_S,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine benzyl ester

Chemical Property:

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Technology Process of (S_S,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine benzyl ester

There total 5 articles about (S_S,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine benzyl ester 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: 97.0%

benzyl (tert-butoxycarbonyl)oxycarbamate + (S,E)-N-benzylidene-tert-butylsulfinamide (186249-74-1) → (SS,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine benzyl ester (878395-96-1)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/jo052298n

Reference yield: 46.0%

(R)-N-benzylidene-2-methylpropane-2-sulfinamide (196929-85-8) + benzyl (tert-butoxycarbonyl)oxycarbamate → (SS,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine benzyl ester (878395-96-1)

Guidance literature:

benzyl (tert-butoxycarbonyl)oxycarbamate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -70 ℃; for 0.5h;

(R)-N-benzylidene-2-methylpropane-2-sulfinamide; In tetrahydrofuran; for 4h;

Reference yield:

benzyl glycolate (30379-58-9) → (SS,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine benzyl ester (878395-96-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap / dichloromethane / 0.5 h / 15 - 80 °C

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -70 °C

2.2: 4 h

With dmap; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

upstream raw materials:

(S,E)-N-benzylidene-tert-butylsulfinamide

benzyl glycolate

(R)-N-benzylidene-2-methylpropane-2-sulfinamide

benzaldehyde

Downstream raw materials:

acide (4S,5R)-N-(tert-butoxycarbonyl)-2-(4-O-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylique

(S_S,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine

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