(3R,4R)-1-Benzyl-4-[(S)-(tert-butyl-dimethyl-silanyloxy)-thiazol-2-yl-methyl]-3-methoxy-azetidin-2-one

Base Information

Chemical Name:(3R,4R)-1-Benzyl-4-[(S)-(tert-butyl-dimethyl-silanyloxy)-thiazol-2-yl-methyl]-3-methoxy-azetidin-2-one
CAS No.:869720-60-5
Molecular Formula:C₂₁H₃₀N₂O₃SSi
Molecular Weight:418.632
Hs Code.:

Synonyms:(3R,4R)-1-Benzyl-4-[(S)-(tert-butyl-dimethyl-silanyloxy)-thiazol-2-yl-methyl]-3-methoxy-azetidin-2-one

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Chemical Property of (3R,4R)-1-Benzyl-4-[(S)-(tert-butyl-dimethyl-silanyloxy)-thiazol-2-yl-methyl]-3-methoxy-azetidin-2-one

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Technology Process of (3R,4R)-1-Benzyl-4-[(S)-(tert-butyl-dimethyl-silanyloxy)-thiazol-2-yl-methyl]-3-methoxy-azetidin-2-one

There total 6 articles about (3R,4R)-1-Benzyl-4-[(S)-(tert-butyl-dimethyl-silanyloxy)-thiazol-2-yl-methyl]-3-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: 67.0%

: 869720-56-9
(3R,4S)-1-Benzyl-4-((S)-hydroxy-thiazol-2-yl-methyl)-3-methoxy-azetidin-2-one

: 69739-34-0
t-butyldimethylsiyl triflate

: 869720-60-5
(3R,4R)-1-Benzyl-4-[(S)-(tert-butyl-dimethyl-silanyloxy)-thiazol-2-yl-methyl]-3-methoxy-azetidin-2-one

Guidance literature:: With dmap; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 5h;
DOI:10.1021/jo051402y

Reference yield:

: 100777-91-1
(2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine

: 869720-60-5
(3R,4R)-1-Benzyl-4-[(S)-(tert-butyl-dimethyl-silanyloxy)-thiazol-2-yl-methyl]-3-methoxy-azetidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂ / 16 h / 20 °C

2: p-TsOH*H₂O / tetrahydrofuran; H₂O / 2 h / Heating

3: 2.1 g / sodium periodate; sodium hydrogen carbonate / H₂O; CH₂Cl₂ / 2 h / 25 °C

4: 23 percent / CH₂Cl₂ / 16 h / 0 °C

5: 67 percent / Et₃N; 4-(dimethylamino)pyridine / dimethylformamide / 5 h / 20 °C

With dmap; sodium periodate; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1: Staudinger reaction;
DOI:10.1021/jo051402y

Reference yield:

: 115828-83-6
(3R,4S)-cis-1-benzyl-3-methoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

: 869720-60-5
(3R,4R)-1-Benzyl-4-[(S)-(tert-butyl-dimethyl-silanyloxy)-thiazol-2-yl-methyl]-3-methoxy-azetidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: p-TsOH*H₂O / tetrahydrofuran; H₂O / 2 h / Heating

2: 2.1 g / sodium periodate; sodium hydrogen carbonate / H₂O; CH₂Cl₂ / 2 h / 25 °C

3: 23 percent / CH₂Cl₂ / 16 h / 0 °C

4: 67 percent / Et₃N; 4-(dimethylamino)pyridine / dimethylformamide / 5 h / 20 °C

With dmap; sodium periodate; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo051402y