(2S,3S)-2-(allyoxy)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-butan-1-ol

Base Information

Chemical Name:(2S,3S)-2-(allyoxy)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-butan-1-ol
CAS No.:866343-60-4
Molecular Formula:C₁₈H₂₆O₄
Molecular Weight:306.402
Hs Code.:

Synonyms:(2S,3S)-2-(allyoxy)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-butan-1-ol

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Chemical Property of (2S,3S)-2-(allyoxy)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-butan-1-ol

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Technology Process of (2S,3S)-2-(allyoxy)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-butan-1-ol

There total 6 articles about (2S,3S)-2-(allyoxy)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-butan-1-ol 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: 98.0%

: 866343-59-1
ethyl (2S,3R)-2-(allyoxy)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-butanoate

: 866343-60-4
(2S,3S)-2-(allyoxy)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-butan-1-ol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 5 - 20 ℃;
DOI:10.1002/chem.200500282

Reference yield:

: 39806-16-1
ethyl (2E,4E)-5-phenyl-penta-2,4-dienoate

: 866343-60-4
(2S,3S)-2-(allyoxy)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-butan-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1,4-bis-(9-O-dihydroquinidinyl)phthalazine; K₃[Fe(CN)6]; K₂OsO₄*2H₂O / K₂CO₃; CH₃SO₂NH₂ / 2-methyl-propan-2-ol / 0 °C

1.2: 8.732 g / p-TsOH*H₂O / acetone / 20 °C

2.1: 72 percent / Me₃SiCl / diethyl ether; hexane / 6 h / -78 °C

3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

3.2: 59 percent / oxodiperoxymolybdenum(pyridine)-hexamethylphosphorictriamide / tetrahydrofuran / 3 h / -78 °C

4.1: NaH / 1,2-dimethoxy-ethane

4.2: 89 percent / 1,2-dimethoxy-ethane / 2 h / 20 - 60 °C

5.1: 98 percent / LiAlH₄ / tetrahydrofuran / 5 - 20 °C

With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; potassium osmate(VI); lithium aluminium tetrahydride; chloro-trimethyl-silane; sodium hydride; potassium hexacyanoferrate(III); lithium diisopropyl amide; methanesulfonamide; potassium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; hexane; tert-butyl alcohol;
DOI:10.1002/chem.200500282

Reference yield:

: 866343-55-7
ethyl (2S,3R)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-2-hydroxybutanoate

: 866343-60-4
(2S,3S)-2-(allyoxy)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-butan-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaH / 1,2-dimethoxy-ethane

1.2: 89 percent / 1,2-dimethoxy-ethane / 2 h / 20 - 60 °C

2.1: 98 percent / LiAlH₄ / tetrahydrofuran / 5 - 20 °C

With lithium aluminium tetrahydride; sodium hydride; In tetrahydrofuran; 1,2-dimethoxyethane;
DOI:10.1002/chem.200500282