(S)-1-[(2R,5R)-5-((E)-(R)-5-Benzyloxy-2,4-dimethyl-pent-3-enyl)-5-methyl-tetrahydro-furan-2-yl]-ethanol

Base Information

Chemical Name:(S)-1-[(2R,5R)-5-((E)-(R)-5-Benzyloxy-2,4-dimethyl-pent-3-enyl)-5-methyl-tetrahydro-furan-2-yl]-ethanol
CAS No.:500102-79-4
Molecular Formula:C₂₁H₃₂O₃
Molecular Weight:332.483
Hs Code.:

Synonyms:(S)-1-[(2R,5R)-5-((E)-(R)-5-Benzyloxy-2,4-dimethyl-pent-3-enyl)-5-methyl-tetrahydro-furan-2-yl]-ethanol

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Chemical Property of (S)-1-[(2R,5R)-5-((E)-(R)-5-Benzyloxy-2,4-dimethyl-pent-3-enyl)-5-methyl-tetrahydro-furan-2-yl]-ethanol

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Technology Process of (S)-1-[(2R,5R)-5-((E)-(R)-5-Benzyloxy-2,4-dimethyl-pent-3-enyl)-5-methyl-tetrahydro-furan-2-yl]-ethanol

There total 14 articles about (S)-1-[(2R,5R)-5-((E)-(R)-5-Benzyloxy-2,4-dimethyl-pent-3-enyl)-5-methyl-tetrahydro-furan-2-yl]-ethanol 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: 95.0%

: 500102-98-7
(2R,5R)-2-((E)-(R)-5-Benzyloxy-2,4-dimethyl-pent-3-enyl)-5-[(S)-1-(4-methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan

: 500102-79-4
(S)-1-[(2R,5R)-5-((E)-(R)-5-Benzyloxy-2,4-dimethyl-pent-3-enyl)-5-methyl-tetrahydro-furan-2-yl]-ethanol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; pH=7;
DOI:10.1002/1521-3773(20021202)41:23<4560::AID-ANIE4560>3.0.CO;2-B

Reference yield:

: 133005-35-3
(2S,3R)-(+)-2,4-dimethyl-4-pentene-1,3-diol

: 500102-79-4
(S)-1-[(2R,5R)-5-((E)-(R)-5-Benzyloxy-2,4-dimethyl-pent-3-enyl)-5-methyl-tetrahydro-furan-2-yl]-ethanol

Guidance literature:: Multi-step reaction with 13 steps

1: imidazole / CH₂Cl₂

2: 52 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂

3: [(cyclopentadienyl)2TiCl₂] / tetrahydrofuran

4: toluene / 110 °C

5: 74 percent / Zn(BH₄)2 / diethyl ether / -78 °C

6: 89 percent / N-iodosuccinimide / acetonitrile / -40 °C

7: 100 percent / Bu₃SnH; 2,2'-azobisisobutyronitrile / toluene

8: 95 percent / tetra-(n-butyl)ammonium fluoride / tetrahydrofuran

9: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂

10: 100 percent / tetrahydrofuran / 65 °C

11: 92 percent / LiAlH₄ / diethyl ether / 0 °C

12: 94 percent / NaH; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; dimethylformamide

13: 95 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / pH 7

With pyridine; 1H-imidazole; dmap; bis(cyclopentadienyl)titanium dichloride; N-iodo-succinimide; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 4: Claisen rearrangement / 10: Wittig reaction;
DOI:10.1002/1521-3773(20021202)41:23<4560::AID-ANIE4560>3.0.CO;2-B

Reference yield:

: 186885-60-9
[[3-(2R,3R)-4R]-3-(3-hydroxy-2,4-dimethyl-1-oxopent-4-enyl)-4-(phenylmethyl)]-2-oxazolidinone

: 500102-79-4
(S)-1-[(2R,5R)-5-((E)-(R)-5-Benzyloxy-2,4-dimethyl-pent-3-enyl)-5-methyl-tetrahydro-furan-2-yl]-ethanol

Guidance literature:: Multi-step reaction with 14 steps

1: LiBH₄ / tetrahydrofuran / 0 °C

2: imidazole / CH₂Cl₂

3: 52 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂

4: [(cyclopentadienyl)2TiCl₂] / tetrahydrofuran

5: toluene / 110 °C

6: 74 percent / Zn(BH₄)2 / diethyl ether / -78 °C

7: 89 percent / N-iodosuccinimide / acetonitrile / -40 °C

8: 100 percent / Bu₃SnH; 2,2'-azobisisobutyronitrile / toluene

9: 95 percent / tetra-(n-butyl)ammonium fluoride / tetrahydrofuran

10: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂

11: 100 percent / tetrahydrofuran / 65 °C

12: 92 percent / LiAlH₄ / diethyl ether / 0 °C

13: 94 percent / NaH; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; dimethylformamide

14: 95 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / pH 7

With pyridine; 1H-imidazole; dmap; bis(cyclopentadienyl)titanium dichloride; N-iodo-succinimide; lithium aluminium tetrahydride; lithium borohydride; zinc(II) tetrahydroborate; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 5: Claisen rearrangement / 11: Wittig reaction;
DOI:10.1002/1521-3773(20021202)41:23<4560::AID-ANIE4560>3.0.CO;2-B