(2R,3S,4S,6S)-4-Benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-6-trimethylsilanyloxy-3-vinyl-cyclohexanone

Base Information

Chemical Name:(2R,3S,4S,6S)-4-Benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-6-trimethylsilanyloxy-3-vinyl-cyclohexanone
CAS No.:326922-38-7
Molecular Formula:C₂₅H₃₈O₅Si
Molecular Weight:446.659
Hs Code.:

Synonyms:(2R,3S,4S,6S)-4-Benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-6-trimethylsilanyloxy-3-vinyl-cyclohexanone

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Chemical Property of (2R,3S,4S,6S)-4-Benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-6-trimethylsilanyloxy-3-vinyl-cyclohexanone

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Technology Process of (2R,3S,4S,6S)-4-Benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-6-trimethylsilanyloxy-3-vinyl-cyclohexanone

There total 12 articles about (2R,3S,4S,6S)-4-Benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-6-trimethylsilanyloxy-3-vinyl-cyclohexanone 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: 53.0%

: 75-77-4
chloro-trimethyl-silane

: 326922-37-6
(2R,3S,4S)-4-(benzyloxy)-3-methyl-2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-3-vinylcyclohexan-1-one

: (2R,3S,4S,6R)-4-Benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-6-trimethylsilanyloxy-3-vinyl-cyclohexanone

: 326922-38-7
(2R,3S,4S,6S)-4-Benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-6-trimethylsilanyloxy-3-vinyl-cyclohexanone

Guidance literature:: Multistep reaction;
DOI:10.1039/b006170k

Reference yield:

: 100-39-0
benzyl bromide

: 326922-38-7
(2R,3S,4S,6S)-4-Benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-6-trimethylsilanyloxy-3-vinyl-cyclohexanone

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / dimethylformamide / 0 °C

1.2: 80 percent / n-Bu₄NI / dimethylformamide / 0 °C

2.1: Hg(OCOCF₃)2 / acetone; H₂O / 0 °C

2.2: 80 percent / MsCl; Et₃N / CH₂Cl₂ / 0 °C

3.1: diethyl ether / -78 °C

4.1: PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

5.1: CuCN / diethyl ether / 0.17 h / -78 °C

5.2: 62 percent / tetrahydrofuran; diethyl ether / 0.25 h / -60 °C

6.1: 90 percent / PPTS / CH₂Cl₂ / 20 °C

7.1: 53 percent

With 4 A molecular sieve; mercury(II) trifluoroacetate; pyridinium p-toluenesulfonate; sodium hydride; pyridinium chlorochromate; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; 2.1: Ferrier's carbocyclization;
DOI:10.1039/b006170k

Reference yield:

: 23339-17-5
methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hexopyranoside

: 326922-38-7
(2R,3S,4S,6S)-4-Benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-6-trimethylsilanyloxy-3-vinyl-cyclohexanone

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaOMe / methanol / 0 °C

1.2: 87 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 20 °C

2.1: NaH / dimethylformamide / 0 °C

2.2: 80 percent / n-Bu₄NI / dimethylformamide / 0 °C

3.1: Hg(OCOCF₃)2 / acetone; H₂O / 0 °C

3.2: 80 percent / MsCl; Et₃N / CH₂Cl₂ / 0 °C

4.1: diethyl ether / -78 °C

5.1: PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

6.1: CuCN / diethyl ether / 0.17 h / -78 °C

6.2: 62 percent / tetrahydrofuran; diethyl ether / 0.25 h / -60 °C

7.1: 90 percent / PPTS / CH₂Cl₂ / 20 °C

8.1: 53 percent

With 4 A molecular sieve; sodium methylate; mercury(II) trifluoroacetate; pyridinium p-toluenesulfonate; sodium hydride; pyridinium chlorochromate; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; 3.1: Ferrier's carbocyclization;
DOI:10.1039/b006170k