(3R,4S)-1-<(S)-1-(tert-butoxycarbonyl)-ethyl>-3-(benzyloxy)-4-phenylazetidin-2-one

Base Information

• Chemical Name: (3R,4S)-1-<(S)-1-(tert-butoxycarbonyl)-ethyl>-3-(benzyloxy)-4-phenylazetidin-2-one
• CAS No.: 98380-70-2
• Molecular Formula: C₂₃H₂₇NO₄
• Molecular Weight: 381.472

Synonyms:(3R,4S)-1-<(S)-1-(tert-butoxycarbonyl)-ethyl>-3-(benzyloxy)-4-phenylazetidin-2-one

Chemical Property of (3R,4S)-1-<(S)-1-(tert-butoxycarbonyl)-ethyl>-3-(benzyloxy)-4-phenylazetidin-2-one

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Technology Process of (3R,4S)-1-<(S)-1-(tert-butoxycarbonyl)-ethyl>-3-(benzyloxy)-4-phenylazetidin-2-one

There total 1 articles about (3R,4S)-1-<(S)-1-(tert-butoxycarbonyl)-ethyl>-3-(benzyloxy)-4-phenylazetidin-2-one 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: 33.0%

Benzyloxyacetyl chloride (19810-31-2) + (S)-N-benzylidene-1-t-butoxycarbonylethylamine (78688-64-9) → (3S,4R)-1-<(S)-1-(tert-butoxycarbonyl)-ethyl>-3-(benzyloxy)-4-phenylazetidin-2-one (98463-80-0) + (3R,4S)-1-<(S)-1-(tert-butoxycarbonyl)-ethyl>-3-(benzyloxy)-4-phenylazetidin-2-one (98380-70-2)

Guidance literature:

With triethylamine;

DOI:10.1016/S0040-4039(00)94772-5

Reference yield: 92.0%

(3R,4S)-1-<(S)-1-(tert-butoxycarbonyl)-ethyl>-3-(benzyloxy)-4-phenylazetidin-2-one (98380-70-2) → (3R,4S)-1-<(S)-1-(hydroxycarbonyl)ethyl>-3-(benzyloxy)-4-phenylazetidin-2-one (98380-68-8)

Guidance literature:

With trifluoroacetic acid; In various solvent(s); at 0 - 25 ℃; for 12h;

DOI:10.1016/S0040-4039(00)94772-5

Reference yield: 89.0%

(3R,4S)-1-<(S)-1-(tert-butoxycarbonyl)-ethyl>-3-(benzyloxy)-4-phenylazetidin-2-one (98380-70-2) → (2S,3S)-1-<(S)-2-hydroxy-1-methylethyl>-2-phenyl-3-(benzyloxy)azetidine (136693-57-7)

Guidance literature:

With chlorohydroalane; In diethyl ether; at 34 ℃; for 4h;

DOI:10.1021/jo00018a012

upstream raw materials:

Benzyloxyacetyl chloride

(S)-N-benzylidene-1-t-butoxycarbonylethylamine

Downstream raw materials:

(3R,4S)-1-<(S)-1-(hydroxycarbonyl)ethyl>-3-(benzyloxy)-4-phenylazetidin-2-one

(2S,3S)-1-<(S)-2-hydroxy-1-methylethyl>-2-phenyl-3-(benzyloxy)azetidine

(3R,4S)-1-<(S)-1-<(benzyloxy)methyl>-3-methylbutyl>-3-<(S)-2-<(3'R,4'S)-3'-(benzyloxy)-2'-oxo-4'-phenylazetidin-1'-yl>propanoyl>-4-phenylazetidin-2-one

(2R,5S,8S,11S)-2,8-dibenzyl-5,13-dimethyl-11-(hydroxymethyl)-1-oxa-4,7,10-triazatetradecane

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