E-(S_S,2S,3S)-(+)-N-p-toluenesulfinyl-2-benzyloxymethyl-2-carbomethoxy-3-phenylaziridine

Base Information

• Chemical Name: E-(S_S,2S,3S)-(+)-N-p-toluenesulfinyl-2-benzyloxymethyl-2-carbomethoxy-3-phenylaziridine
• CAS No.: 365402-91-1
• Molecular Formula: C₂₅H₂₅NO₄S
• Molecular Weight: 435.544

Synonyms:E-(S_S,2S,3S)-(+)-N-p-toluenesulfinyl-2-benzyloxymethyl-2-carbomethoxy-3-phenylaziridine

Chemical Property of E-(S_S,2S,3S)-(+)-N-p-toluenesulfinyl-2-benzyloxymethyl-2-carbomethoxy-3-phenylaziridine

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Technology Process of E-(S_S,2S,3S)-(+)-N-p-toluenesulfinyl-2-benzyloxymethyl-2-carbomethoxy-3-phenylaziridine

There total 1 articles about E-(S_S,2S,3S)-(+)-N-p-toluenesulfinyl-2-benzyloxymethyl-2-carbomethoxy-3-phenylaziridine 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: 70.0%

(S,E)-N-benzylidene-4-methylbenzenesulfinamide (350479-90-2) + 2-bromo-3-(phenylmethoxy)propanoic acid methyl ester (113933-16-7) → (2R,3S)-2-Benzyloxymethyl-3-phenyl-1-((S)-toluene-4-sulfinyl)-aziridine-2-carboxylic acid methyl ester + E-(SS,2S,3S)-(+)-N-p-toluenesulfinyl-2-benzyloxymethyl-2-carbomethoxy-3-phenylaziridine (365402-91-1)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1016/S0040-4020(01)00500-2

Reference yield: 89.0%

E-(SS,2S,3S)-(+)-N-p-toluenesulfinyl-2-benzyloxymethyl-2-carbomethoxy-3-phenylaziridine (365402-91-1) → methyl E-(2S,3S)-(-)-2-benzyloxymethyl-3-phenyl-1H-aziridine-2-carboxylate (365402-92-2)

Guidance literature:

With trifluoroacetic acid; In water; acetone; at 20 ℃; for 0.25h;

DOI:10.1016/S0040-4020(01)00500-2

Reference yield:

E-(SS,2S,3S)-(+)-N-p-toluenesulfinyl-2-benzyloxymethyl-2-carbomethoxy-3-phenylaziridine (365402-91-1) → (S)-(+)-2-amino-2-hydroxymethyl-3-phenylpropionic acid methyl ester (365402-94-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / TFA / acetone; H₂O / 0.25 h / 20 °C

2: 98 percent / H₂ / Pd(OH)2 / tetrahydrofuran / 8 h / 20 °C

3: 97 percent / H₂; TFA / Pd(OH)2 / ethanol; tetrahydrofuran / 8 h / 20 °C

With hydrogen; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; ethanol; water; acetone;

DOI:10.1016/S0040-4020(01)00500-2

upstream raw materials:

(S,E)-N-benzylidene-4-methylbenzenesulfinamide

2-bromo-3-(phenylmethoxy)propanoic acid methyl ester

Downstream raw materials:

methyl E-(2S,3S)-(-)-2-benzyloxymethyl-3-phenyl-1H-aziridine-2-carboxylate

(S)-α-(hydroxymethyl)-D-phenylalanine

(S)-(+)-2-amino-2-hydroxymethyl-3-phenylpropionic acid methyl ester

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