(4S)-4-benzyloxycarbonylamino-6',7'-epoxy-1',3,4,4',4'a,8'a-hexahydrospiro[furan-2(5H),5'(8'H)-1',4'-methanonaphthalene]-5',8'-dione

Base Information

Chemical Name:(4S)-4-benzyloxycarbonylamino-6',7'-epoxy-1',3,4,4',4'a,8'a-hexahydrospiro[furan-2(5H),5'(8'H)-1',4'-methanonaphthalene]-5',8'-dione
CAS No.:942618-30-6
Molecular Formula:C₂₂H₂₁NO₆
Molecular Weight:395.412
Hs Code.:

Synonyms:(4S)-4-benzyloxycarbonylamino-6',7'-epoxy-1',3,4,4',4'a,8'a-hexahydrospiro[furan-2(5H),5'(8'H)-1',4'-methanonaphthalene]-5',8'-dione

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Chemical Property of (4S)-4-benzyloxycarbonylamino-6',7'-epoxy-1',3,4,4',4'a,8'a-hexahydrospiro[furan-2(5H),5'(8'H)-1',4'-methanonaphthalene]-5',8'-dione

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Technology Process of (4S)-4-benzyloxycarbonylamino-6',7'-epoxy-1',3,4,4',4'a,8'a-hexahydrospiro[furan-2(5H),5'(8'H)-1',4'-methanonaphthalene]-5',8'-dione

There total 1 articles about (4S)-4-benzyloxycarbonylamino-6',7'-epoxy-1',3,4,4',4'a,8'a-hexahydrospiro[furan-2(5H),5'(8'H)-1',4'-methanonaphthalene]-5',8'-dione 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:

: 542-92-7,25568-84-7,7313-32-8
cyclopenta-1,3-diene

: 141406-16-8
(3S)-3-<(Benzyloxycarbonyl)amino>-1-oxaspiro<4.5>deca-7,10-diene-2,8-dione

: 942618-30-6
(4S)-4-benzyloxycarbonylamino-6',7'-epoxy-1',3,4,4',4'a,8'a-hexahydrospiro[furan-2(5H),5'(8'H)-1',4'-methanonaphthalene]-5',8'-dione

: (4S)-4-benzyloxycarbonylamino-6',7'-epoxy-1',3,4,4',4'a,8'a-hexahydrospiro[furan-2(5H),5'(8'H)-1',4'-methanonaphthalene]-5',8'-dione

Guidance literature:: cyclopenta-1,3-diene; (3S)-3-<(Benzyloxycarbonyl)amino>-1-oxaspiro<4.5>deca-7,10-diene-2,8-dione; In dichloromethane; at 20 ℃; for 72h;

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 ℃; for 6h;

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20 ℃; for 18h; Further stages.;
DOI:10.1021/jo070337k

Reference yield: 83.0%

: 942618-30-6
(4S)-4-benzyloxycarbonylamino-6',7'-epoxy-1',3,4,4',4'a,8'a-hexahydrospiro[furan-2(5H),5'(8'H)-1',4'-methanonaphthalene]-5',8'-dione

: 942618-57-7
C₂₂H₂₃NO₆

Guidance literature:: With samarium diiodide; In tetrahydrofuran; methanol; at 78 ℃; for 1h;
DOI:10.1021/jo070337k

Reference yield:

: 942618-30-6
(4S)-4-benzyloxycarbonylamino-6',7'-epoxy-1',3,4,4',4'a,8'a-hexahydrospiro[furan-2(5H),5'(8'H)-1',4'-methanonaphthalene]-5',8'-dione

: 942618-38-4
(2'S,2''E,4R,4''E,5R,6S,6''E,8''R,10''S,12''E,14''R)-4,5-epoxy-6-hydroxy-6-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxypropyl]-2-cyclohexen-1-one

Guidance literature:: Multi-step reaction with 12 steps

1: 83 percent / SmI₂ / methanol; tetrahydrofuran / 1 h / 78 °C

2: 100 percent / imidazole / CH₂Cl₂ / 14 h / 20 °C

3: 100 percent / maleic anhydride / diphenyl ether / 1 h / 230 °C

4: 95 percent / NaBH₄; CeCl₃*7H₂O / propan-2-ol; tetrahydrofuran / 0.67 h / 0 °C

5: 99 percent / mCPBA / CH₂Cl₂ / 24 h / 20 °C

6: 90 percent / 1,4-diazabicyclo[2.2.2]octane / CH₂Cl₂ / 7 h / 20 °C

7: 99 percent / NaBH₄ / ethanol; tetrahydrofuran / 5 h / 20 °C

8: 99 percent / TBAF / tetrahydrofuran / 0.33 h / 20 °C

9: 96 percent / imidazole / dimethylformamide / 24 h / 20 °C

10: aq. HCl; H₂ / PtO₂ / methanol / 0.33 h / 20 °C / 760.05 Torr

11: 64 percent / EDCI / CH₂Cl₂ / 14 h / 20 °C

12: 71 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; maleic anhydride; hydrogenchloride; sodium tetrahydroborate; samarium diiodide; cerium(III) chloride; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; platinum(IV) oxide; In tetrahydrofuran; methanol; diphenylether; ethanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; 12: Swern oxidation;
DOI:10.1021/jo070337k