benzyl (5S)-5-[(1R,2S)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Base Information

• Chemical Name: benzyl (5S)-5-[(1R,2S)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS No.: 1429470-97-2
• Molecular Formula: C₁₇H₂₃NO₆
• Molecular Weight: 337.373
• Mol file: 1429470-97-2.mol

Synonyms:benzyl (5S)-5-[(1R,2S)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Chemical Property of benzyl (5S)-5-[(1R,2S)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (5S)-5-[(1R,2S)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

There total 7 articles about benzyl (5S)-5-[(1R,2S)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 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: 48.0%

benzyl (S)-5-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (134038-74-7) + hydroxy-2-propanone (116-09-6) → benzyl (5S)-5-[(1R,2R)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1429471-04-4) + benzyl (5S)-5-[(1S,2S)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1429471-03-3) + benzyl (5S)-5-[(1S,2R)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1429470-96-1) + benzyl (5S)-5-[(1R,2S)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1429470-97-2)

Guidance literature:

With CH₃C₆H₂(O)(CH₂N(CH₂)3CHC(C₆H₅)2O)2Zn₂C₂H₅; In tetrahydrofuran; at -20 - 5 ℃; for 12h; Reagent/catalyst; Solvent; Overall yield = 72 %; Overall yield = 128 mg; diastereoselective reaction; Inert atmosphere;

DOI:10.1039/c7ob02797d

Reference yield:

benzyl (5R)-2,2-dimethyl-5-[(1Z)-3-oxobut-1-en-1-yl]-1,3-oxazolidine-3-carboxylate (1429470-99-4) → benzyl (5S)-5-[(1S,2R)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1429470-96-1) + benzyl (5S)-5-[(1R,2S)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1429470-97-2)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; tert-butyl alcohol; at 25 ℃; for 24h; Overall yield = 85 %; Overall yield = 0.097 g; diastereoselective reaction;

DOI:10.1002/ejoc.201201413

Reference yield:

(S)-(2,2-dimethyl-5-oxo-[1,3]dioxalan-4-ylmethyl)carbamic acid benzyl ester (385836-99-7) → benzyl (5S)-5-[(1S,2R)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1429470-96-1) + benzyl (5S)-5-[(1R,2S)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1429470-97-2)

Guidance literature:

Multi-step reaction with 6 steps

1: toluene-4-sulfonic acid / 25 °C / Inert atmosphere

2: boron trifluoride diethyl etherate / acetone / 6.5 h / 25 °C / Inert atmosphere

3: sodium tetrahydroborate; calcium chloride / ethanol / 19 h / 0 - 25 °C / Inert atmosphere

4: Dess-Martin periodane / dichloromethane / 18 h / 25 °C / Inert atmosphere

5: dichloromethane / 3 h / 25 °C

6: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; tetrahydrofuran; tert-butyl alcohol / 24 h / 25 °C

With sodium tetrahydroborate; osmium(VIII) oxide; boron trifluoride diethyl etherate; Dess-Martin periodane; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; calcium chloride; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; tert-butyl alcohol; 5: |Wittig Olefination;

DOI:10.1002/ejoc.201201413

upstream raw materials:

benzyl (5R)-2,2-dimethyl-5-[(1Z)-3-oxobut-1-en-1-yl]-1,3-oxazolidine-3-carboxylate

(S)-(2,2-dimethyl-5-oxo-[1,3]dioxalan-4-ylmethyl)carbamic acid benzyl ester

benzyl (S)-5-hydroxymethyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

(S)-methyl 3-(benzyloxycarbonylamino)-2-hydroxypropanoate