Benzoic acid (2R,3S)-3-benzyloxy-2-hydroxy-4-((R)-5-oxo-2,5-dihydro-furan-2-yl)-butyl ester

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Chemical Name:Benzoic acid (2R,3S)-3-benzyloxy-2-hydroxy-4-((R)-5-oxo-2,5-dihydro-furan-2-yl)-butyl ester
CAS No.:165178-36-9
Molecular Formula:C₂₂H₂₂O₆
Molecular Weight:382.413
Hs Code.:

Synonyms:Benzoic acid (2R,3S)-3-benzyloxy-2-hydroxy-4-((R)-5-oxo-2,5-dihydro-furan-2-yl)-butyl ester

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Chemical Property of Benzoic acid (2R,3S)-3-benzyloxy-2-hydroxy-4-((R)-5-oxo-2,5-dihydro-furan-2-yl)-butyl ester

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Technology Process of Benzoic acid (2R,3S)-3-benzyloxy-2-hydroxy-4-((R)-5-oxo-2,5-dihydro-furan-2-yl)-butyl ester

There total 4 articles about Benzoic acid (2R,3S)-3-benzyloxy-2-hydroxy-4-((R)-5-oxo-2,5-dihydro-furan-2-yl)-butyl ester 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: 83.0%

: 98-88-4
benzoyl chloride

: 160998-98-1
(5R)-5-<(2S,3R)-2-benzyloxy-3,4-dihydroxybutyl>-2(5H)-furanone

: 165178-36-9
Benzoic acid (2R,3S)-3-benzyloxy-2-hydroxy-4-((R)-5-oxo-2,5-dihydro-furan-2-yl)-butyl ester

Guidance literature:: With pyridine; 1.) 0 deg C, 1 h, 2.) 22 deg C, 3 h;

Reference yield:

: 103795-36-4
(3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal

: 165178-36-9
Benzoic acid (2R,3S)-3-benzyloxy-2-hydroxy-4-((R)-5-oxo-2,5-dihydro-furan-2-yl)-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) 1.6M BuLi / 1.) THF, Et₂O, pentane, hexane, -78 deg C, 15 min, 2.) THF, Et₂O, pentane, hexane, -78 deg C; quenching with Me₃SiCl

2: 1.) H₂, quinoline, 2.) TsOH / 1.) 5percent Pd/BaSO₄ / 1.) methanol, 22 deg C, 1 bar, 2.) methanol, pH 2.5, 22 deg C, 15 h

3: 83 percent / pyridine / 1.) 0 deg C, 1 h, 2.) 22 deg C, 3 h

With pyridine; quinoline; n-butyllithium; hydrogen; toluene-4-sulfonic acid; Pd-BaSO₄;

Reference yield:

: 87604-53-3
(R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane

: 165178-36-9
Benzoic acid (2R,3S)-3-benzyloxy-2-hydroxy-4-((R)-5-oxo-2,5-dihydro-furan-2-yl)-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) O₃, 2.) PPh₃ / 1.) methanol, -78 deg C, 2.) methanol, 12 h

2: 1.) 1.6M BuLi / 1.) THF, Et₂O, pentane, hexane, -78 deg C, 15 min, 2.) THF, Et₂O, pentane, hexane, -78 deg C; quenching with Me₃SiCl

3: 1.) H₂, quinoline, 2.) TsOH / 1.) 5percent Pd/BaSO₄ / 1.) methanol, 22 deg C, 1 bar, 2.) methanol, pH 2.5, 22 deg C, 15 h

4: 83 percent / pyridine / 1.) 0 deg C, 1 h, 2.) 22 deg C, 3 h

With pyridine; quinoline; n-butyllithium; hydrogen; toluene-4-sulfonic acid; ozone; triphenylphosphine; Pd-BaSO₄;