(3S,4S,5R)-5-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-3-hydroxy-4-methyl-dihydro-furan-2-one

Base Information

Chemical Name:(3S,4S,5R)-5-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-3-hydroxy-4-methyl-dihydro-furan-2-one
CAS No.:121960-66-5
Molecular Formula:C₁₇H₂₂O₄
Molecular Weight:290.359
Hs Code.:

Synonyms:(3S,4S,5R)-5-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-3-hydroxy-4-methyl-dihydro-furan-2-one

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Chemical Property of (3S,4S,5R)-5-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-3-hydroxy-4-methyl-dihydro-furan-2-one

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Technology Process of (3S,4S,5R)-5-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-3-hydroxy-4-methyl-dihydro-furan-2-one

There total 10 articles about (3S,4S,5R)-5-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-3-hydroxy-4-methyl-dihydro-furan-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: 40.0%

: 111149-35-0
(3S,4S,5S)-(E)-8-benzyloxy-4-hydroxy-3,5-dimethyloct-6-enoic acid lactone

: 121960-66-5
(3S,4S,5R)-5-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-3-hydroxy-4-methyl-dihydro-furan-2-one

: 121896-46-6
(3R,4S,5R)-5-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-3-hydroxy-4-methyl-dihydro-furan-2-one

Guidance literature:: With MoO₅*pyridine*HMPA; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;
DOI:10.1246/cl.1988.2041

Reference yield:

: 111149-31-6
(3R,4S)-(E)-7-benzyloxy-4-methyl-1-trimethylsilylhept-5-en-1-yn-3-ol

: 121960-66-5
(3S,4S,5R)-5-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-3-hydroxy-4-methyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: n-Bu₄NF / tetrahydrofuran / Ambient temperature

2: 87 percent / imidazole / dimethylformamide / Ambient temperature

3: 1.)n-BuLi / 1.) THF, -72 deg C; 2.) THF, -45 deg C

4: H₂ / Lindlar catalyst / benzene / Ambient temperature

5: concd. HCl / methanol / Ambient temperature

6: 87 percent / CuI / diethyl ether / 0 °C

7: 42 percent / LDA, MoOPh / tetrahydrofuran / -78 °C

With 1H-imidazole; hydrogenchloride; copper(l) iodide; n-butyllithium; MoO₅*pyridine*HMPA; tetrabutyl ammonium fluoride; hydrogen; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; benzene;
DOI:10.1246/cl.1988.2041

Reference yield:

: 120448-41-1
(3R,4S)-(E)-7-benzyloxy-4-methylhept-5-en-1-yn-3-ol

: 121960-66-5
(3S,4S,5R)-5-((E)-(S)-4-Benzyloxy-1-methyl-but-2-enyl)-3-hydroxy-4-methyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / imidazole / dimethylformamide / Ambient temperature

2: 1.)n-BuLi / 1.) THF, -72 deg C; 2.) THF, -45 deg C

3: H₂ / Lindlar catalyst / benzene / Ambient temperature

4: concd. HCl / methanol / Ambient temperature

5: 87 percent / CuI / diethyl ether / 0 °C

6: 42 percent / LDA, MoOPh / tetrahydrofuran / -78 °C

With 1H-imidazole; hydrogenchloride; copper(l) iodide; n-butyllithium; MoO₅*pyridine*HMPA; hydrogen; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; benzene;
DOI:10.1246/cl.1988.2041