(3S,4R)-4-(1-Benzyloxy-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one

Base Information

Chemical Name:(3S,4R)-4-(1-Benzyloxy-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one
CAS No.:141993-95-5
Molecular Formula:C₂₁H₃₅NO₄Si
Molecular Weight:393.599
Hs Code.:

Synonyms:(3S,4R)-4-(1-Benzyloxy-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one

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Chemical Property of (3S,4R)-4-(1-Benzyloxy-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one

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Technology Process of (3S,4R)-4-(1-Benzyloxy-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one

There total 4 articles about (3S,4R)-4-(1-Benzyloxy-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-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: 68.0%

: 141964-96-7
(2S,3S,4S)-4-Benzyloxy-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-pentanoic acid methoxy-amide

: 141993-95-5
(3S,4R)-4-(1-Benzyloxy-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one

Guidance literature:: With dimethyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 1.5h;
DOI:10.1016/S0040-4039(00)91648-4

Reference yield:

: 81445-44-5
(S)-2-(benzyloxy)propanal

: 141993-95-5
(3S,4R)-4-(1-Benzyloxy-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 2) 1N HCl / 1) Pr(fod)3 / 1) CH₂Cl₂, -40 deg C, 2) THF

2: 93 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

3: 82 percent / Me₃Al / toluene / 2 h / Ambient temperature

4: 68 percent / Ph₃P, dimethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 °C

With 1H-imidazole; hydrogenchloride; trimethylaluminum; dimethyl azodicarboxylate; triphenylphosphine; (tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato))praseodymium(III); In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(00)91648-4

Reference yield:

: 141964-94-5
(2S,3S,4S)-4-Benzyloxy-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-pentanoic acid methyl ester

: 141993-95-5
(3S,4R)-4-(1-Benzyloxy-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 82 percent / Me₃Al / toluene / 2 h / Ambient temperature

2: 68 percent / Ph₃P, dimethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 °C

With trimethylaluminum; dimethyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; toluene;
DOI:10.1016/S0040-4039(00)91648-4