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

Base Information

Chemical Name:7-exo-<(benzyloxy)methyl>-α-1-(hydroxydimethylsilyl)-α-3,7-dimethylbicyclo<4.1.0>heptane β-2,α-4-dicarbamate
CAS No.:143143-83-3
Molecular Formula:C₃₃H₄₀N₂O₆Si
Molecular Weight:588.776
Hs Code.:

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

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

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

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

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

: 143143-83-3
7-exo-<(benzyloxy)methyl>-α-1-(hydroxydimethylsilyl)-α-3,7-dimethylbicyclo<4.1.0>heptane β-2,α-4-dicarbamate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; for 6h; Ambient temperature;
DOI:10.1021/jo00046a017

Reference yield:

: 100-39-0
benzyl bromide

: 143143-83-3
7-exo-<(benzyloxy)methyl>-α-1-(hydroxydimethylsilyl)-α-3,7-dimethylbicyclo<4.1.0>heptane β-2,α-4-dicarbamate

Guidance literature:: Multi-step reaction with 5 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

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; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00046a017

Reference yield:

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

: 143143-83-3
7-exo-<(benzyloxy)methyl>-α-1-(hydroxydimethylsilyl)-α-3,7-dimethylbicyclo<4.1.0>heptane β-2,α-4-dicarbamate

Guidance literature:: Multi-step reaction with 7 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

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; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo00046a017