(3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-3-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester

Base Information

Chemical Name:(3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-3-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester
CAS No.:903907-90-4
Molecular Formula:C₁₉H₂₄N₂O₆
Molecular Weight:376.409
Hs Code.:

Synonyms:(3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-3-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester

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Chemical Property of (3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-3-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester

Chemical Property:

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Technology Process of (3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-3-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester

There total 10 articles about (3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-3-hydroxy-cyclohex-1-enecarboxylic acid ethyl 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:

: 903907-80-2
[(2S)-benzyloxycarbonylamino-4-(tert-butyldiphenylsilanyloxymethyl)-(1R)-hydroxymethyl-pent-4-enyl]carbamic acid tert-butyl ester

: 903907-90-4
(3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-3-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 1.81 g / ZnBr₂ / tetrahydrofuran / 6 h / -70 - -30 °C

2: 98 percent / DIPEA / CH₂Cl₂ / 24 h / 20 °C

3: 98 percent / 2nd generation Grubbs catalyst / CH₂Cl₂ / 24 h / 20 °C

4: 96 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

5: 4 Angstroem molecular sieves; PCC / CH₂Cl₂ / 2 h / 20 °C

6: 342 mg / 2,3-dimethyl-1,3-butadiene; NaClO₂; KH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 6 h / 20 °C

7: 85 percent / DIPEA; HOBt*H₂O; EDCI / CH₂Cl₂ / 6 h / 20 °C

8: HCl / ethanol / 0 - 20 °C

9: 262 mg / Na₂CO₃ / ethanol

With hydrogenchloride; sodium chlorite; potassium dihydrogenphosphate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,3-dimethyl-buta-1,3-diene; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; zinc dibromide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; ethanol; dichloromethane; water; tert-butyl alcohol; 1: Grignard addition;
DOI:10.1021/jo060633h

Reference yield:

: 903907-79-9
tert-butyl (R)-4-((S)-11,11-dimethyl-7-methylene-3-oxo-1,10,10-triphenyl-2,9-dioxa-4-aza-10-sila dodecan-5-yl)-2,2-dimethyloxazolidine-3-carboxylate

: 903907-90-4
(3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-3-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 89 percent / BiBr₃ / acetonitrile / 5 h / 20 °C

2: 1.81 g / ZnBr₂ / tetrahydrofuran / 6 h / -70 - -30 °C

3: 98 percent / DIPEA / CH₂Cl₂ / 24 h / 20 °C

4: 98 percent / 2nd generation Grubbs catalyst / CH₂Cl₂ / 24 h / 20 °C

5: 96 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

6: 4 Angstroem molecular sieves; PCC / CH₂Cl₂ / 2 h / 20 °C

7: 342 mg / 2,3-dimethyl-1,3-butadiene; NaClO₂; KH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 6 h / 20 °C

8: 85 percent / DIPEA; HOBt*H₂O; EDCI / CH₂Cl₂ / 6 h / 20 °C

9: HCl / ethanol / 0 - 20 °C

10: 262 mg / Na₂CO₃ / ethanol

With hydrogenchloride; sodium chlorite; potassium dihydrogenphosphate; bismuth(III) bromide; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,3-dimethyl-buta-1,3-diene; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; zinc dibromide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile; tert-butyl alcohol; 2: Grignard addition;
DOI:10.1021/jo060633h

Reference yield:

: 903907-81-3
[(2R)-benzyloxycarbonylamino-4-(tert-butyldiphenylsilanyloxymethyl)-(1R)-((1R)-hydroxy-allyl)-pent-4-enyl]carbamic acid tert-butyl ester

: 903907-90-4
(3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-3-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / DIPEA / CH₂Cl₂ / 24 h / 20 °C

2: 98 percent / 2nd generation Grubbs catalyst / CH₂Cl₂ / 24 h / 20 °C

3: 96 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

4: 4 Angstroem molecular sieves; PCC / CH₂Cl₂ / 2 h / 20 °C

5: 342 mg / 2,3-dimethyl-1,3-butadiene; NaClO₂; KH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 6 h / 20 °C

6: 85 percent / DIPEA; HOBt*H₂O; EDCI / CH₂Cl₂ / 6 h / 20 °C

7: HCl / ethanol / 0 - 20 °C

8: 262 mg / Na₂CO₃ / ethanol

With hydrogenchloride; sodium chlorite; potassium dihydrogenphosphate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,3-dimethyl-buta-1,3-diene; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; ethanol; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo060633h