7-exo-<(benzyloxy)methyl>-β-2,α-4-diacetoxy-α-3,7-dimethylbicyclo<4.1.0>heptan-1α-ol

Base Information

Chemical Name:7-exo-<(benzyloxy)methyl>-β-2,α-4-diacetoxy-α-3,7-dimethylbicyclo<4.1.0>heptan-1α-ol
CAS No.:143143-80-0
Molecular Formula:C₂₁H₂₈O₆
Molecular Weight:376.45
Hs Code.:

Synonyms:7-exo-<(benzyloxy)methyl>-β-2,α-4-diacetoxy-α-3,7-dimethylbicyclo<4.1.0>heptan-1α-ol

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Chemical Property of 7-exo-<(benzyloxy)methyl>-β-2,α-4-diacetoxy-α-3,7-dimethylbicyclo<4.1.0>heptan-1α-ol

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Technology Process of 7-exo-<(benzyloxy)methyl>-β-2,α-4-diacetoxy-α-3,7-dimethylbicyclo<4.1.0>heptan-1α-ol

There total 9 articles about 7-exo-<(benzyloxy)methyl>-β-2,α-4-diacetoxy-α-3,7-dimethylbicyclo<4.1.0>heptan-1α-ol 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: 82.0%

: 143143-79-7
7-exo-<(benzyloxy)methyl>-α-1-(fluorodimethylsilyl)-β-2,α-4-diacetoxy-α-3,7-dimethylbicyclo<4.1.0>heptane

: 143143-80-0
7-exo-<(benzyloxy)methyl>-β-2,α-4-diacetoxy-α-3,7-dimethylbicyclo<4.1.0>heptan-1α-ol

Guidance literature:: With potassium fluoride; dihydrogen peroxide; potassium hydrogencarbonate; In tetrahydrofuran; methanol; for 8h; Ambient temperature;
DOI:10.1021/jo00046a017

Reference yield:

: 100-39-0
benzyl bromide

: 143143-80-0
7-exo-<(benzyloxy)methyl>-β-2,α-4-diacetoxy-α-3,7-dimethylbicyclo<4.1.0>heptan-1α-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 42.2 percent / NaH, n-Bu₄NI / tetrahydrofuran / 3 h

2: 1.) LDA, HMPA / 1.) THF, r. t., 14 h

3: 55 percent / AlCl₃, LiAlH₄ / diethyl ether; tetrahydrofuran / 6 h / Ambient temperature

4: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 21 h / Ambient temperature

5: 79 percent / HF*Py, Br₂ / CH₂Cl₂ / 2 h / Ambient temperature

6: 82 percent / KHCO₃, KF, 30percent aq. H₂O₂ / tetrahydrofuran; methanol / 8 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium fluoride; lithium aluminium tetrahydride; aluminium trichloride; dihydrogen peroxide; bromine; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium hydrogencarbonate; pyridine hydrogenfluoride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/jo00046a017

Reference yield:

: 39903-97-4
(S)-carvone oxide

: 143143-80-0
7-exo-<(benzyloxy)methyl>-β-2,α-4-diacetoxy-α-3,7-dimethylbicyclo<4.1.0>heptan-1α-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 81 percent / m-CPBA / CH₂Cl₂ / 6 h

2: t-BuOK / 2-methyl-propan-2-ol / 5 h / 20 °C / <20 deg C

3: 42.2 percent / NaH, n-Bu₄NI / tetrahydrofuran / 3 h

4: 1.) LDA, HMPA / 1.) THF, r. t., 14 h

5: 55 percent / AlCl₃, LiAlH₄ / diethyl ether; tetrahydrofuran / 6 h / Ambient temperature

6: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 21 h / Ambient temperature

7: 79 percent / HF*Py, Br₂ / CH₂Cl₂ / 2 h / Ambient temperature

8: 82 percent / KHCO₃, KF, 30percent aq. H₂O₂ / tetrahydrofuran; methanol / 8 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium fluoride; lithium aluminium tetrahydride; aluminium trichloride; potassium tert-butylate; dihydrogen peroxide; bromine; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium hydrogencarbonate; pyridine hydrogenfluoride; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; tert-butyl alcohol;
DOI:10.1021/jo00046a017