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

Base Information

Chemical Name:7-exo-<(benzyloxy)methyl>-α-1-(fluorodimethylsilyl)-β-2,α-4-(dicarbamoyloxy)-α-3,7-dimethylbicyclo<4.1.0>heptane
CAS No.:143143-84-4
Molecular Formula:C₃₃H₃₉FN₂O₅Si
Molecular Weight:590.767
Hs Code.:

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

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Chemical Property of 7-exo-<(benzyloxy)methyl>-α-1-(fluorodimethylsilyl)-β-2,α-4-(dicarbamoyloxy)-α-3,7-dimethylbicyclo<4.1.0>heptane

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Technology Process of 7-exo-<(benzyloxy)methyl>-α-1-(fluorodimethylsilyl)-β-2,α-4-(dicarbamoyloxy)-α-3,7-dimethylbicyclo<4.1.0>heptane

There total 9 articles about 7-exo-<(benzyloxy)methyl>-α-1-(fluorodimethylsilyl)-β-2,α-4-(dicarbamoyloxy)-α-3,7-dimethylbicyclo<4.1.0>heptane 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: 90.0%

: 143143-82-2
α-1-(allyldimethylsilyl)-7-exo-<(benzyloxy)methyl>-β-2,α-4-(dicarbamoyloxy)-α-3,7-dimethylbicyclo<4.1.0>heptane

: 143143-84-4
7-exo-<(benzyloxy)methyl>-α-1-(fluorodimethylsilyl)-β-2,α-4-(dicarbamoyloxy)-α-3,7-dimethylbicyclo<4.1.0>heptane

Guidance literature:: With pyridine; bromine; pyridine hydrogenfluoride; In dichloromethane; for 5h; 0 deg C - r. t.;
DOI:10.1021/jo00046a017

Reference yield:

: 100-39-0
benzyl bromide

: 143143-84-4
7-exo-<(benzyloxy)methyl>-α-1-(fluorodimethylsilyl)-β-2,α-4-(dicarbamoyloxy)-α-3,7-dimethylbicyclo<4.1.0>heptane

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: 85 percent / pyridine, DMAP / CH₂Cl₂ / 9 h / Ambient temperature

5: 100 percent / TBAF / tetrahydrofuran; dimethylformamide / 6 h / Ambient temperature

6: 628 mg / HF*pyridine, pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; aluminium trichloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridine hydrogenfluoride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00046a017

Reference yield:

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

: 143143-84-4
7-exo-<(benzyloxy)methyl>-α-1-(fluorodimethylsilyl)-β-2,α-4-(dicarbamoyloxy)-α-3,7-dimethylbicyclo<4.1.0>heptane

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: 85 percent / pyridine, DMAP / CH₂Cl₂ / 9 h / Ambient temperature

7: 100 percent / TBAF / tetrahydrofuran; dimethylformamide / 6 h / Ambient temperature

8: 628 mg / HF*pyridine, pyridine / CH₂Cl₂ / 2 h / Ambient temperature

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