N-[(2'R,3'S)-4'-(tert-Butyldiphenylsilyloxy)-2',3'-methanobutanoyl]-(S)-cysteine methyl ester

Base Information

Chemical Name:N-[(2'R,3'S)-4'-(tert-Butyldiphenylsilyloxy)-2',3'-methanobutanoyl]-(S)-cysteine methyl ester
CAS No.:251444-06-1
Molecular Formula:C₂₅H₃₃NO₄SSi
Molecular Weight:471.693
Hs Code.:

Synonyms:N-[(2'R,3'S)-4'-(tert-Butyldiphenylsilyloxy)-2',3'-methanobutanoyl]-(S)-cysteine methyl ester

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Chemical Property of N-[(2'R,3'S)-4'-(tert-Butyldiphenylsilyloxy)-2',3'-methanobutanoyl]-(S)-cysteine methyl ester

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Technology Process of N-[(2'R,3'S)-4'-(tert-Butyldiphenylsilyloxy)-2',3'-methanobutanoyl]-(S)-cysteine methyl ester

There total 6 articles about N-[(2'R,3'S)-4'-(tert-Butyldiphenylsilyloxy)-2',3'-methanobutanoyl]-(S)-cysteine 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:

: 18598-63-5
L-cysteine methyl ester hydrochloride

: 251444-05-0
C₂₆H₃₄O₅Si

: 251444-06-1
N-[(2'R,3'S)-4'-(tert-Butyldiphenylsilyloxy)-2',3'-methanobutanoyl]-(S)-cysteine methyl ester

Guidance literature:: With 4-methyl-morpholine; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1039/a904378k

Reference yield:

: 154001-53-3
(1Z,4'S)-3-<(tert-Butyldiphenylsilyl)oxy>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-propene

: 251444-06-1
N-[(2'R,3'S)-4'-(tert-Butyldiphenylsilyloxy)-2',3'-methanobutanoyl]-(S)-cysteine methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / Et₂Zn / hexane; CH₂Cl₂ / -23 - 0 °C

2: 100 percent / H₅IO₆ / diethyl ether / 10 h / 20 °C

3: 97 percent / KMnO₄; potassium hydrogen orthophosphate buffer; H₂O / 2-methyl-propan-2-ol / 0.08 h / pH 4.4

4: N-methylmorpholine / CH₂Cl₂ / 0.25 h / -10 °C

5: N-methylmorpholine / CH₂Cl₂ / 2 h / 20 °C

With 4-methyl-morpholine; potassium permanganate; potassium hydrogen orthophosphate buffer; water; diethylzinc; periodic acid; In diethyl ether; hexane; dichloromethane; tert-butyl alcohol; 1: Addition / 2: Oxidation / 3: Oxidation / 4: Substitution / 5: Acylation;
DOI:10.1039/a904378k

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 251444-06-1
N-[(2'R,3'S)-4'-(tert-Butyldiphenylsilyloxy)-2',3'-methanobutanoyl]-(S)-cysteine methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / Et₃N; DMAP / CH₂Cl₂

2: 97 percent / Et₂Zn / hexane; CH₂Cl₂ / -23 - 0 °C

3: 100 percent / H₅IO₆ / diethyl ether / 10 h / 20 °C

4: 97 percent / KMnO₄; potassium hydrogen orthophosphate buffer; H₂O / 2-methyl-propan-2-ol / 0.08 h / pH 4.4

5: N-methylmorpholine / CH₂Cl₂ / 0.25 h / -10 °C

6: N-methylmorpholine / CH₂Cl₂ / 2 h / 20 °C

With 4-methyl-morpholine; dmap; potassium permanganate; potassium hydrogen orthophosphate buffer; water; diethylzinc; periodic acid; triethylamine; In diethyl ether; hexane; dichloromethane; tert-butyl alcohol; 1: Etherification / 2: Addition / 3: Oxidation / 4: Oxidation / 5: Substitution / 6: Acylation;
DOI:10.1039/a904378k