(S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1S)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine methyl ester

Base Information

Chemical Name:(S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1S)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine methyl ester
CAS No.:137330-22-4
Molecular Formula:C₁₈H₂₇ClN₂O₆
Molecular Weight:402.875
Hs Code.:

Synonyms:(S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1S)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine methyl ester

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Chemical Property of (S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1S)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine methyl ester

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Technology Process of (S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1S)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine methyl ester

There total 11 articles about (S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1S)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine 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: 56.0%

: (S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(4S/R)-3-chloro-4-hydroxy-2-cyclohexen-1-yl>alanine methyl ester

: 137330-22-4
(S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1S)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine methyl ester

: 137232-93-0
(S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1R)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine methyl ester

Guidance literature:: With manganese(IV) oxide; In dichloromethane; for 3h;
DOI:10.1021/jo00089a019

Reference yield:

: 137232-86-1
(3S,6R)-2,5-Dimethoxy-6-isopropyl-3-<(4-oxo-1-cyclohexenyl)methyl>-3,6-dihydro-1,4-pyrazine

: 137330-22-4
(S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1S)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 97 percent / H₂ / Pd-C / ethyl acetate / 2 h / 2280 Torr

2: 76 percent / (R,R)-lithium-bis(phenylethyl)amid / tetrahydrofuran / -78 °C

3: 1) MeLi / 1) THF, 0 deg C, 2) THF, -78 deg C

4: TosN₃, NEt₃ / acetonitrile / 2 h

5: 1) PhSeCl, 2) H₂O₂, pyridine / 1) CH₂Cl₂, -5 deg C, 2) CH₂Cl₂, 0 deg C, 1 h

6: 89 percent / NaBH₄, CeCl₃ / methanol

7: HCl / acetonitrile; H₂O / 2 h

8: dicyclohexylcarbodiimide, hydroxybenzotriazole / tetrahydrofuran / 1 h

9: MnO₂ / CH₂Cl₂ / 6 h

With pyridine; hydrogenchloride; manganese(IV) oxide; sodium tetrahydroborate; 4-toluenesulfonyl azide; Phenylselenyl chloride; cerium(III) chloride; methyllithium; hydrogen; dihydrogen peroxide; lithium [R(R*,R*)]-(+)-bis(α-methylbenzyl)amide; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetonitrile;

Reference yield:

: 137232-95-2,137331-07-8
(S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1R,4S/R)-3-chloro-4-hydroxy-2-cyclohexen-1-yl>alanine methyl ester

: 137330-22-4
(S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1S)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine methyl ester

: 137232-93-0
(S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1R)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine methyl ester

Guidance literature:: With manganese(IV) oxide; In dichloromethane; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1021/jo00089a019