(3R,4R,5S)-5-benzyloxycarbonylamino-4-tert-butyloxycarbonylamino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid ethyl ester

Base Information

Chemical Name:(3R,4R,5S)-5-benzyloxycarbonylamino-4-tert-butyloxycarbonylamino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid ethyl ester
CAS No.:903907-89-1
Molecular Formula:C₂₄H₃₄N₂O₈
Molecular Weight:478.543
Hs Code.:

Synonyms:(3R,4R,5S)-5-benzyloxycarbonylamino-4-tert-butyloxycarbonylamino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid ethyl ester

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Chemical Property of (3R,4R,5S)-5-benzyloxycarbonylamino-4-tert-butyloxycarbonylamino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid ethyl ester

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Technology Process of (3R,4R,5S)-5-benzyloxycarbonylamino-4-tert-butyloxycarbonylamino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid ethyl ester

There total 8 articles about (3R,4R,5S)-5-benzyloxycarbonylamino-4-tert-butyloxycarbonylamino-3-methoxymethoxy-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: 85.0%

: 903907-88-0
(3R,4R,5S)-5-Benzyloxycarbonylamino-4-tert-butoxycarbonylamino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid

: 64-17-5
ethanol

: 903907-89-1
(3R,4R,5S)-5-benzyloxycarbonylamino-4-tert-butyloxycarbonylamino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 6h;
DOI:10.1021/jo060633h

Reference yield:

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

: 903907-89-1
(3R,4R,5S)-5-benzyloxycarbonylamino-4-tert-butyloxycarbonylamino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 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

With sodium chlorite; potassium dihydrogenphosphate; 4 A molecular sieve; tetrabutyl ammonium fluoride; 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; 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

: 903907-89-1
(3R,4R,5S)-5-benzyloxycarbonylamino-4-tert-butyloxycarbonylamino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 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

With sodium chlorite; potassium dihydrogenphosphate; bismuth(III) bromide; 4 A molecular sieve; tetrabutyl ammonium fluoride; 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; dichloromethane; water; acetonitrile; tert-butyl alcohol; 2: Grignard addition;
DOI:10.1021/jo060633h