[(2S,3R)-2-((S)-1-Benzyloxy-ethyl)-5-hydroxy-tetrahydro-furan-3-yl]-acetic acid

Base Information

Chemical Name:[(2S,3R)-2-((S)-1-Benzyloxy-ethyl)-5-hydroxy-tetrahydro-furan-3-yl]-acetic acid
CAS No.:473806-61-0
Molecular Formula:C₁₅H₂₀O₅
Molecular Weight:280.321
Hs Code.:

Synonyms:[(2S,3R)-2-((S)-1-Benzyloxy-ethyl)-5-hydroxy-tetrahydro-furan-3-yl]-acetic acid

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Chemical Property of [(2S,3R)-2-((S)-1-Benzyloxy-ethyl)-5-hydroxy-tetrahydro-furan-3-yl]-acetic acid

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Technology Process of [(2S,3R)-2-((S)-1-Benzyloxy-ethyl)-5-hydroxy-tetrahydro-furan-3-yl]-acetic acid

There total 8 articles about [(2S,3R)-2-((S)-1-Benzyloxy-ethyl)-5-hydroxy-tetrahydro-furan-3-yl]-acetic acid 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:

: 473806-57-4
[(2S,3S)-2-((S)-1-Benzyloxy-ethyl)-5-oxo-tetrahydro-furan-3-yl]-acetic acid

: 473806-61-0
[(2S,3R)-2-((S)-1-Benzyloxy-ethyl)-5-hydroxy-tetrahydro-furan-3-yl]-acetic acid

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 - 0 ℃; for 0.666667h;
DOI:10.1016/S0040-4039(02)01053-5

Reference yield:

: 2396-84-1
(2E,4E)-ethyl hexa-2,4-dienoate

: 473806-61-0
[(2S,3R)-2-((S)-1-Benzyloxy-ethyl)-5-hydroxy-tetrahydro-furan-3-yl]-acetic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: α-AD-mix; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 18 h / 4 °C

1.2: TsOH / acetone

2.1: 58 percent / NaOEt / ethanol / 4 h / 20 °C

3.1: 58 percent / NaCl; H₂O / dimethylsulfoxide / 0.25 h / Irradiation; microwave

4.1: 42 percent / CF₃COOH / ethanol; CH₂Cl₂

5.1: 76 percent / MeSO₃H / cyclohexane; CH₂Cl₂ / 4 h / 20 °C

6.1: 65 percent / Bacillus licheniformis protease Novozyme 243 / various solvent(s); diisopropyl ether / pH 6.8

7.1: DIBAL / toluene / 0.67 h / -78 - 0 °C

With methanesulfonic acid; methanesulfonamide; α-AD mix {K4[Fe(CN)6], OsO4, Na2CO3, (DHQ)2-PHAL}; Bacillus licheniformis protease Novozyme 243; water; sodium ethanolate; diisobutylaluminium hydride; trifluoroacetic acid; sodium chloride; In ethanol; dichloromethane; di-isopropyl ether; cyclohexane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol;
DOI:10.1016/S0040-4039(02)01053-5

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 473806-61-0
[(2S,3R)-2-((S)-1-Benzyloxy-ethyl)-5-hydroxy-tetrahydro-furan-3-yl]-acetic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 76 percent / MeSO₃H / cyclohexane; CH₂Cl₂ / 4 h / 20 °C

2: 65 percent / Bacillus licheniformis protease Novozyme 243 / various solvent(s); diisopropyl ether / pH 6.8

3: DIBAL / toluene / 0.67 h / -78 - 0 °C

With methanesulfonic acid; Bacillus licheniformis protease Novozyme 243; diisobutylaluminium hydride; In dichloromethane; di-isopropyl ether; cyclohexane; toluene;
DOI:10.1016/S0040-4039(02)01053-5