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

Base Information

Chemical Name:(3R,4R,5S)-5-Benzyloxycarbonylamino-4-tert-butoxycarbonylamino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid
CAS No.:903907-88-0
Molecular Formula:C₂₂H₃₀N₂O₈
Molecular Weight:450.489
Hs Code.:

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

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Chemical Property of (3R,4R,5S)-5-Benzyloxycarbonylamino-4-tert-butoxycarbonylamino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid

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Technology Process of (3R,4R,5S)-5-Benzyloxycarbonylamino-4-tert-butoxycarbonylamino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid

There total 6 articles about (3R,4R,5S)-5-Benzyloxycarbonylamino-4-tert-butoxycarbonylamino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid 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

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

Guidance literature:: Multi-step reaction with 6 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

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

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

Guidance literature:: Multi-step reaction with 7 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

With sodium chlorite; potassium dihydrogenphosphate; bismuth(III) bromide; 4 A molecular sieve; tetrabutyl ammonium fluoride; 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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

With sodium chlorite; potassium dihydrogenphosphate; 4 A molecular sieve; tetrabutyl ammonium fluoride; 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; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo060633h