(3S,4S,5R)-4-Hydroxy-3-((S)-hydroxy-phenyl-methyl)-5-methyl-dihydro-furan-2-one

Base Information

Chemical Name:(3S,4S,5R)-4-Hydroxy-3-((S)-hydroxy-phenyl-methyl)-5-methyl-dihydro-furan-2-one
CAS No.:90108-59-1
Molecular Formula:C₁₂H₁₄O₄
Molecular Weight:222.241
Hs Code.:

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4S,5R)-4-Hydroxy-3-((S)-hydroxy-phenyl-methyl)-5-methyl-dihydro-furan-2-one

Chemical Property:

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Technology Process of (3S,4S,5R)-4-Hydroxy-3-((S)-hydroxy-phenyl-methyl)-5-methyl-dihydro-furan-2-one

There total 8 articles about (3S,4S,5R)-4-Hydroxy-3-((S)-hydroxy-phenyl-methyl)-5-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:

: 78138-89-3
2-Bromo-2-deoxy-D-arabinono-γ-lactone

: 90108-59-1
(3S,4S,5R)-4-Hydroxy-3-((S)-hydroxy-phenyl-methyl)-5-methyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 1. H₂ 2. CBr₄, PPh₃ / 1. Pd-C / 1. EtOAc, NEt₃ 2. CH₃CN, 0.5 h, room temperature

2: 91.7 percent / tri-n-butyltin hydride, AIBN / toluene / 18 h / 90 °C

3: 1. lithium diisopropylamide 2. ZnCl₂ / 1. THF, -78 deg C 2. -50 deg C, THF

With 2,2'-azobis(isobutyronitrile); carbon tetrabromide; hydrogen; tri-n-butyl-tin hydride; triphenylphosphine; lithium diisopropyl amide; palladium on activated charcoal; In toluene;
DOI:10.1021/jo00186a018

Reference yield:

: 78138-88-2
2,5-Dibromo-2,5-dideoxy-D-arabinono-γ-lactone

: 90108-59-1
(3S,4S,5R)-4-Hydroxy-3-((S)-hydroxy-phenyl-methyl)-5-methyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / H₂, NEt₃ / Pd-C / ethyl acetate

2: 91.7 percent / tri-n-butyltin hydride, AIBN / toluene / 18 h / 90 °C

3: 1. lithium diisopropylamide 2. ZnCl₂ / 1. THF, -78 deg C 2. -50 deg C, THF

With 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In ethyl acetate; toluene;
DOI:10.1021/jo00186a018

Reference yield:

: 20603-44-5,104445-18-3,131614-82-9,131614-83-0
3,5-O-Benzylidene-D-ribonic Acid γ-Lactone

: 90108-59-1
(3S,4S,5R)-4-Hydroxy-3-((S)-hydroxy-phenyl-methyl)-5-methyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 1. sodium hydride / 1. dimethylformamide, room temperature, 30 min 2. 30 min, room temperature

2: 92.5 percent / tri-n-butyltin hydride, AIBN / toluene / 2 h / Heating

3: 1. CF₃COOH 2. CBr₄, PPh₃ / 1. CHCl₃, H₂O, 10 h, reflux

4: 91.7 percent / tri-n-butyltin hydride, AIBN / toluene / 18 h / 90 °C

5: 1. lithium diisopropylamide 2. ZnCl₂ / 1. THF, -78 deg C 2. -50 deg C, THF

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; triphenylphosphine; trifluoroacetic acid; lithium diisopropyl amide; In toluene;
DOI:10.1021/jo00186a018