(4R,5R,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-one

Base Information

Chemical Name:(4R,5R,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-one
CAS No.:713141-54-9
Molecular Formula:C₂₅H₃₂O₃Si
Molecular Weight:408.613
Hs Code.:

Synonyms:(4R,5R,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-one

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Chemical Property of (4R,5R,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-one

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Technology Process of (4R,5R,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-one

There total 6 articles about (4R,5R,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-one 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: 61.0%

: 713141-53-8
tert-Butyl-[(2S,3R,4R)-6-methoxy-3-methyl-2-((E)-propenyl)-tetrahydro-pyran-4-yloxy]-diphenyl-silane

: 713141-54-9
(4R,5R,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-one

Guidance literature:: tert-Butyl-[(2S,3R,4R)-6-methoxy-3-methyl-2-((E)-propenyl)-tetrahydro-pyran-4-yloxy]-diphenyl-silane; With acetic acid; at 70 ℃;

With dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran;
DOI:10.3987/COM-04-10034

Reference yield:

: 8-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-oct-3-en-2-one

: 713141-54-9
(4R,5R,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 96 percent / (R)-Me-CBS; BMS / CH₂Cl₂

2.1: 88 percent / p-TsOH / CH₂Cl₂

3.1: 62 percent / HF*pyridine / tetrahydrofuran

4.1: 87 percent / IBX; DMSO / tetrahydrofuran

5.1: 80 percent / PdCl₂(PhCN)2 / methanol; tetrahydrofuran

6.1: aq. AcOH / 70 °C

6.2: 61 percent / IBX; DMSO / tetrahydrofuran

With dimethylsulfide borane complex; toluene-4-sulfonic acid; pyridine hydrogenfluoride; acetic acid; dimethyl sulfoxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; bis(benzonitrile)palladium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.3987/COM-04-10034

Reference yield:

: 713141-51-6
(E)-(3R,4R,7S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-7-(tetrahydro-pyran-2-yloxy)-oct-5-en-1-ol

: 713141-54-9
(4R,5R,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 87 percent / IBX; DMSO / tetrahydrofuran

2.1: 80 percent / PdCl₂(PhCN)2 / methanol; tetrahydrofuran

3.1: aq. AcOH / 70 °C

3.2: 61 percent / IBX; DMSO / tetrahydrofuran

With acetic acid; dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; bis(benzonitrile)palladium(II) dichloride; In tetrahydrofuran; methanol;
DOI:10.3987/COM-04-10034