(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-carbaldehyde

Base Information

Chemical Name:(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-carbaldehyde
CAS No.:779356-68-2
Molecular Formula:C₂₇H₃₄O₄
Molecular Weight:422.565
Hs Code.:

Synonyms:(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-carbaldehyde

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Chemical Property of (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-carbaldehyde

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Technology Process of (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-carbaldehyde

There total 10 articles about (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-carbaldehyde 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: 99.0%

: 779356-92-2
[(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-methanol

: 779356-68-2
(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: With pyridine-SO₃ complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/ol048418f

Reference yield:

: 6728-31-0
(Z)-4-heptenal

: 779356-68-2
(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 9 steps

1.1: hexamethyldisilazane / CH₂Cl₂ / 18 h / 35 °C

1.2: 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.5 h / -78 °C

1.3: 86 percent / trifluoromethanesulfonic acid / CH₂Cl₂

2.1: ethyl trimethylacetate / tetrahydrofuran / 22 h / Heating

2.2: 100 percent / celite / tetrahydrofuran; hexane / 2 h / 20 °C

3.1: 77 percent / dimethylaluminum chloride; cesium carbonate / CH₂Cl₂ / 1.58 h / -78 - 20 °C

4.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

4.2: 78 percent / (1S)-3,3-dimethoxy-(10-camphorsulfonyl)oxaziridine; hexamethylphosphoramide / tetrahydrofuran; CH₂Cl₂ / 2 h / -60 °C

5.1: 4.32 g / K₂CO₃ / methanol / 1 h

6.1: chlorotrimethylsilane; 4-dimethylaminopyridine; imidazole / CH₂Cl₂ / 24 h / 20 °C

6.2: 85 percent / tetrabutylammonium borohydride / CH₂Cl₂ / 3.5 h / -78 - -40 °C

7.1: 100 percent / sodium hydride / dimethylformamide; tetrahydrofuran / 6 h / 20 °C

8.1: 100 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.05 h / 20 °C

9.1: 99 percent / DMSO; SO₃*Py; N,N-diisopropylethylamine / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; dmap; chloro-trimethyl-silane; ammonium cerium(IV) nitrate; pyridine-SO₃ complex; 2,2-dimethyl-propanoic acid ethyl ester; dimethylaluminum chloride; potassium hexamethylsilazane; sodium hydride; potassium carbonate; caesium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 2.1: Petasis-Tebbe methylenation / 3.1: Petasis-Ferrier rearrangement / 9.1: Parikh-Doering oxidation;
DOI:10.1021/ol048418f

Reference yield:

: 779356-69-3
(2R,3R)-3-Hydroxy-4-(4-methoxy-phenoxy)-2-methyl-butyric acid

: 779356-68-2
(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 9 steps

1.1: hexamethyldisilazane / CH₂Cl₂ / 18 h / 35 °C

1.2: 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.5 h / -78 °C

1.3: 86 percent / trifluoromethanesulfonic acid / CH₂Cl₂

2.1: ethyl trimethylacetate / tetrahydrofuran / 22 h / Heating

2.2: 100 percent / celite / tetrahydrofuran; hexane / 2 h / 20 °C

3.1: 77 percent / dimethylaluminum chloride; cesium carbonate / CH₂Cl₂ / 1.58 h / -78 - 20 °C

4.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

4.2: 78 percent / (1S)-3,3-dimethoxy-(10-camphorsulfonyl)oxaziridine; hexamethylphosphoramide / tetrahydrofuran; CH₂Cl₂ / 2 h / -60 °C

5.1: 4.32 g / K₂CO₃ / methanol / 1 h

6.1: chlorotrimethylsilane; 4-dimethylaminopyridine; imidazole / CH₂Cl₂ / 24 h / 20 °C

6.2: 85 percent / tetrabutylammonium borohydride / CH₂Cl₂ / 3.5 h / -78 - -40 °C

7.1: 100 percent / sodium hydride / dimethylformamide; tetrahydrofuran / 6 h / 20 °C

8.1: 100 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.05 h / 20 °C

9.1: 99 percent / DMSO; SO₃*Py; N,N-diisopropylethylamine / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; dmap; chloro-trimethyl-silane; ammonium cerium(IV) nitrate; pyridine-SO₃ complex; 2,2-dimethyl-propanoic acid ethyl ester; dimethylaluminum chloride; potassium hexamethylsilazane; sodium hydride; potassium carbonate; caesium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 2.1: Petasis-Tebbe methylenation / 3.1: Petasis-Ferrier rearrangement / 9.1: Parikh-Doering oxidation;
DOI:10.1021/ol048418f