(1S,2S,3S,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Base Information

Chemical Name:(1S,2S,3S,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
CAS No.:792910-58-8
Molecular Formula:C₁₂H₁₇NO₅
Molecular Weight:255.271
Hs Code.:

Synonyms:(1S,2S,3S,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

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Chemical Property of (1S,2S,3S,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

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Technology Process of (1S,2S,3S,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

There total 1 articles about (1S,2S,3S,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic 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:

: (1S,2S,3S,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

: 792910-58-8,148257-14-1
(1S,2S,3S,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Guidance literature:: With lithium hydroxide; In methanol; water; at 20 ℃; for 18h;
DOI:10.1021/ol0484106

Reference yield:

: 792910-58-8,148257-14-1
(1S,2S,3S,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

: 792911-08-1
Benzyl-((2R,3S,3aS,8aS)-4-oxo-2-vinyl-2,3,3a,4,6,8a-hexahydro-furo[3,2-c]oxepin-3-yl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: Cs₂CO₃ / methanol; H₂O / pH 7

1.2: 66 percent / dimethylformamide / 20 °C

2.1: 78 percent / NaH / dimethylformamide / 0.5 h / 20 °C

3.1: (N,N'-Mes₂imidazolidin-2-yl)Ru=CHPh(PCy₃)Cl₂ / CH₂Cl₂ / 1 h / 20 °C

3.2: CH₂Cl₂ / 2 h / 20 °C

3.3: 57 percent / CH₂Cl₂ / 4 h / Heating

With sodium hydride; caesium carbonate; tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol0484106

Reference yield:

: 792910-58-8,148257-14-1
(1S,2S,3S,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

: (2S,3S,3aS,7aR)-3-[Benzyl-((2R,3S,3aS,8aS)-4-oxo-2-vinyl-2,3,3a,4,6,8a-hexahydro-furo[3,2-c]oxepin-3-yl)-carbamoyl]-2-vinyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyridine-4-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: Cs₂CO₃ / methanol; H₂O / pH 7

1.2: 66 percent / dimethylformamide / 20 °C

2.1: 78 percent / NaH / dimethylformamide / 0.5 h / 20 °C

3.1: TFA / CH₂Cl₂ / 1 h / 0 - 20 °C

3.2: 56 percent / aq. KHCO₃ / CH₂Cl₂ / 0.75 h

4.1: 39 percent / DIPEA / CH₂Cl₂ / 1 h / 0 - 20 °C

5.1: (N,N'-Mes₂imidazolidin-2-yl)Ru=CHPh(PCy₃)Cl₂ / CH₂Cl₂ / 2 h / 25 °C

5.2: 2 h / 25 °C

5.3: 7 percent / CH₂Cl₂ / 20 h / Heating

With sodium hydride; caesium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol0484106