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

Base Information

• Chemical Name: (S_S,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine methyl ester
• CAS No.: 878395-97-2
• Molecular Formula: C₁₉H₂₉NO₆S
• Molecular Weight: 399.508

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

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

Chemical Property:

Purity/Quality:

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

There total 1 articles about (S_S,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine methyl 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: 96.0%

tert-butoxycarbonyloxyacetic acid methyl ester (878395-91-6) + (S,E)-N-benzylidene-tert-butylsulfinamide (186249-74-1) → (SS,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine methyl ester (878395-97-2,911199-16-1)

Guidance literature:

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

DOI:10.1021/jo052298n

Reference yield:

(SS,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine methyl ester (878395-97-2,911199-16-1) → methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate (32981-85-4)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / methanol / 1 h

2: 0.123 g / NaHCO₃ / H₂O; tetrahydrofuran / 2 h / 0 °C

With hydrogenchloride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo052298n

Reference yield:

(SS,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine methyl ester (878395-97-2,911199-16-1) → (2R,3S)-3-phenylisoserine methyl ester (157240-36-3)

Guidance literature:

With hydrogenchloride; In methanol; for 1h;

DOI:10.1021/jo052298n

upstream raw materials:

tert-butoxycarbonyloxyacetic acid methyl ester

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

Downstream raw materials:

(2R,3S)-3-phenylisoserine methyl ester

methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

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