(1S,4R,4'S,4aS,5S,6S,8aR)-4'-benzyloxycarbonylamino-6-triethylsilyloxy-1,3',4',4,4a,6,7,8a-octahydrospiro[furan-2'(5H),5(8H)-1,4-methanonaphthalene]-5',8-dione

Base Information

Chemical Name:(1S,4R,4'S,4aS,5S,6S,8aR)-4'-benzyloxycarbonylamino-6-triethylsilyloxy-1,3',4',4,4a,6,7,8a-octahydrospiro[furan-2'(5H),5(8H)-1,4-methanonaphthalene]-5',8-dione
CAS No.:942618-31-7
Molecular Formula:C₂₈H₃₇NO₆Si
Molecular Weight:511.69
Hs Code.:

(1S,4R,4'S,4aS,5S,6S,8aR)-4'-benzyloxycarbonylamino-6-triethylsilyloxy-1,3',4',4,4a,6,7,8a-octahydrospiro[furan-2'(5H),5(8H)-1,4-methanonaphthalene]-5',8-dione

Synonyms:(1S,4R,4'S,4aS,5S,6S,8aR)-4'-benzyloxycarbonylamino-6-triethylsilyloxy-1,3',4',4,4a,6,7,8a-octahydrospiro[furan-2'(5H),5(8H)-1,4-methanonaphthalene]-5',8-dione

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Chemical Property of (1S,4R,4'S,4aS,5S,6S,8aR)-4'-benzyloxycarbonylamino-6-triethylsilyloxy-1,3',4',4,4a,6,7,8a-octahydrospiro[furan-2'(5H),5(8H)-1,4-methanonaphthalene]-5',8-dione

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Technology Process of (1S,4R,4'S,4aS,5S,6S,8aR)-4'-benzyloxycarbonylamino-6-triethylsilyloxy-1,3',4',4,4a,6,7,8a-octahydrospiro[furan-2'(5H),5(8H)-1,4-methanonaphthalene]-5',8-dione

There total 3 articles about (1S,4R,4'S,4aS,5S,6S,8aR)-4'-benzyloxycarbonylamino-6-triethylsilyloxy-1,3',4',4,4a,6,7,8a-octahydrospiro[furan-2'(5H),5(8H)-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: 100.0%

: 942618-57-7
C₂₂H₂₃NO₆

: 994-30-9
triethylsilyl chloride

: 942618-31-7
(1S,4R,4'S,4aS,5S,6S,8aR)-4'-benzyloxycarbonylamino-6-triethylsilyloxy-1,3',4',4,4a,6,7,8a-octahydrospiro[furan-2'(5H),5(8H)-1,4-methanonaphthalene]-5',8-dione

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 14h;
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

: 942618-31-7
(1S,4R,4'S,4aS,5S,6S,8aR)-4'-benzyloxycarbonylamino-6-triethylsilyloxy-1,3',4',4,4a,6,7,8a-octahydrospiro[furan-2'(5H),5(8H)-1,4-methanonaphthalene]-5',8-dione

Guidance literature:: Multi-step reaction with 2 steps

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

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

With 1H-imidazole; samarium diiodide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo070337k

Reference yield:

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

: 942618-31-7
(1S,4R,4'S,4aS,5S,6S,8aR)-4'-benzyloxycarbonylamino-6-triethylsilyloxy-1,3',4',4,4a,6,7,8a-octahydrospiro[furan-2'(5H),5(8H)-1,4-methanonaphthalene]-5',8-dione

Guidance literature:: Multi-step reaction with 3 steps

1.1: CH₂Cl₂ / 72 h / 20 °C

1.2: aq. H₂O₂; aq. LiOH / tetrahydrofuran / 6 h / 0 °C

1.3: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / CH₂Cl₂ / 18 h / 20 °C

2.1: 83 percent / SmI₂ / methanol; tetrahydrofuran / 1 h / 78 °C

3.1: 100 percent / imidazole / CH₂Cl₂ / 14 h / 20 °C

With 1H-imidazole; samarium diiodide; In tetrahydrofuran; methanol; dichloromethane; 1.1: Diels-Alder reaction;
DOI:10.1021/jo070337k