(1S,3R,4S,5S)-5-Benzyloxy-4-methyl-2-methylene-3-(tetrahydro-pyran-2-yloxymethyl)-4-vinyl-cyclohexanol

Base Information

Chemical Name:(1S,3R,4S,5S)-5-Benzyloxy-4-methyl-2-methylene-3-(tetrahydro-pyran-2-yloxymethyl)-4-vinyl-cyclohexanol
CAS No.:326922-39-8
Molecular Formula:C₂₃H₃₂O₄
Molecular Weight:372.505
Hs Code.:

Synonyms:(1S,3R,4S,5S)-5-Benzyloxy-4-methyl-2-methylene-3-(tetrahydro-pyran-2-yloxymethyl)-4-vinyl-cyclohexanol

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Chemical Property of (1S,3R,4S,5S)-5-Benzyloxy-4-methyl-2-methylene-3-(tetrahydro-pyran-2-yloxymethyl)-4-vinyl-cyclohexanol

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Technology Process of (1S,3R,4S,5S)-5-Benzyloxy-4-methyl-2-methylene-3-(tetrahydro-pyran-2-yloxymethyl)-4-vinyl-cyclohexanol

There total 13 articles about (1S,3R,4S,5S)-5-Benzyloxy-4-methyl-2-methylene-3-(tetrahydro-pyran-2-yloxymethyl)-4-vinyl-cyclohexanol 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: 64.0%

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

: 326922-39-8
(1S,3R,4S,5S)-5-Benzyloxy-4-methyl-2-methylene-3-(tetrahydro-pyran-2-yloxymethyl)-4-vinyl-cyclohexanol

Guidance literature:: (2R,3S,4S,6S)-4-Benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-6-trimethylsilanyloxy-3-vinyl-cyclohexanone; Tebbe reagent; In tetrahydrofuran; at 20 ℃;

With potassium carbonate; In methanol; at 20 ℃;
DOI:10.1039/b006170k

Reference yield:

: 100-39-0
benzyl bromide

: 326922-39-8
(1S,3R,4S,5S)-5-Benzyloxy-4-methyl-2-methylene-3-(tetrahydro-pyran-2-yloxymethyl)-4-vinyl-cyclohexanol

Guidance literature:: Multi-step reaction with 8 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

8.1: tetrahydrofuran / 20 °C

8.2: 64 percent / K₂CO₃ / methanol / 20 °C

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

Reference yield:

: 136611-27-3
4-<(benzyl)oxy>-3-methyl-2-cyclohexenone

: 326922-39-8
(1S,3R,4S,5S)-5-Benzyloxy-4-methyl-2-methylene-3-(tetrahydro-pyran-2-yloxymethyl)-4-vinyl-cyclohexanol

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 62 percent / tetrahydrofuran; diethyl ether / 0.25 h / -60 °C

2.1: 90 percent / PPTS / CH₂Cl₂ / 20 °C

3.1: 53 percent

4.1: tetrahydrofuran / 20 °C

4.2: 64 percent / K₂CO₃ / methanol / 20 °C

With pyridinium p-toluenesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1039/b006170k