[(S)-1-((2R,5S)-5-Methyl-2,5-dihydro-furan-2-yl)-2-oxo-ethyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(S)-1-((2R,5S)-5-Methyl-2,5-dihydro-furan-2-yl)-2-oxo-ethyl]-carbamic acid benzyl ester
• CAS No.: 221546-68-5
• Molecular Formula: C₁₅H₁₇NO₄
• Molecular Weight: 275.304
• Mol file: 221546-68-5.mol

Synonyms:[(S)-1-((2R,5S)-5-Methyl-2,5-dihydro-furan-2-yl)-2-oxo-ethyl]-carbamic acid benzyl ester

Chemical Property of [(S)-1-((2R,5S)-5-Methyl-2,5-dihydro-furan-2-yl)-2-oxo-ethyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(S)-1-((2R,5S)-5-Methyl-2,5-dihydro-furan-2-yl)-2-oxo-ethyl]-carbamic acid benzyl ester

There total 28 articles about [(S)-1-((2R,5S)-5-Methyl-2,5-dihydro-furan-2-yl)-2-oxo-ethyl]-carbamic acid benzyl 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:

L-xylose (609-06-3) → [(S)-1-((2R,5S)-5-Methyl-2,5-dihydro-furan-2-yl)-2-oxo-ethyl]-carbamic acid benzyl ester (221546-68-5)

Guidance literature:

Multi-step reaction with 16 steps

1: HCl / 5 - 10 °C

2: pyridine / 24 h

3: 1.) acetic acid, acetic anhydride, H₂SO₄, 2.) BF₃*OEt₂ / 1.) room temperature, overnight, 2.) CH₂Cl₂, 0 deg C, 36 h

4: 99 percent / K₂CO₃ / tetrahydrofuran; methanol / 0.33 h

5: 89 percent / p-toluenesulfonic acid monohydrate / 1.5 h

6: 95 percent / 1,3-dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h

7: 96 percent / camphorsulfonic acid / methanol / 3.5 h

8: 75 percent / tributylphosphine / tetrahydrofuran / 1.5 h

9: 42 percent / Ph₃SnH, azobis(isobutyronitrile) / toluene / 2 h / Heating

10: LiAlH₄ / tetrahydrofuran

11: 236.0 mg / imidazole / tetrahydrofuran / 6 h

12: camphorsulfonic acid, hydrogen / Pd-C / ethyl acetate; methanol / 2 h / 2585.74 Torr

13: 171.5 mg / NaHCO₃ / tetrahydrofuran; H₂O

14: 64 percent / triphenylphosphine, iodomethane, imidazole / toluene / 22 h / Heating

15: 96 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h

16: Dess-Martin reagent / CH₂Cl₂ / 0.5 h

With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tributylphosphine; sulfuric acid; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; triphenylstannane; tetrabutyl ammonium fluoride; hydrogen; acetic anhydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; triphenylphosphine; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1021/jo982205k

Reference yield:

(2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol (13039-67-3) → [(S)-1-((2R,5S)-5-Methyl-2,5-dihydro-furan-2-yl)-2-oxo-ethyl]-carbamic acid benzyl ester (221546-68-5)

Guidance literature:

Multi-step reaction with 15 steps

1: pyridine / 24 h

2: 1.) acetic acid, acetic anhydride, H₂SO₄, 2.) BF₃*OEt₂ / 1.) room temperature, overnight, 2.) CH₂Cl₂, 0 deg C, 36 h

3: 99 percent / K₂CO₃ / tetrahydrofuran; methanol / 0.33 h

4: 89 percent / p-toluenesulfonic acid monohydrate / 1.5 h

5: 95 percent / 1,3-dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h

6: 96 percent / camphorsulfonic acid / methanol / 3.5 h

7: 75 percent / tributylphosphine / tetrahydrofuran / 1.5 h

8: 42 percent / Ph₃SnH, azobis(isobutyronitrile) / toluene / 2 h / Heating

9: LiAlH₄ / tetrahydrofuran

10: 236.0 mg / imidazole / tetrahydrofuran / 6 h

11: camphorsulfonic acid, hydrogen / Pd-C / ethyl acetate; methanol / 2 h / 2585.74 Torr

12: 171.5 mg / NaHCO₃ / tetrahydrofuran; H₂O

13: 64 percent / triphenylphosphine, iodomethane, imidazole / toluene / 22 h / Heating

14: 96 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h

15: Dess-Martin reagent / CH₂Cl₂ / 0.5 h

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tributylphosphine; sulfuric acid; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; triphenylstannane; tetrabutyl ammonium fluoride; hydrogen; acetic anhydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; triphenylphosphine; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1021/jo982205k

Reference yield:

phenyl 1-seleno-β-L-xylofuranoside (221546-56-1) → [(S)-1-((2R,5S)-5-Methyl-2,5-dihydro-furan-2-yl)-2-oxo-ethyl]-carbamic acid benzyl ester (221546-68-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 89 percent / p-toluenesulfonic acid monohydrate / 1.5 h

2: 95 percent / 1,3-dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h

3: 96 percent / camphorsulfonic acid / methanol / 3.5 h

4: 75 percent / tributylphosphine / tetrahydrofuran / 1.5 h

5: 42 percent / Ph₃SnH, azobis(isobutyronitrile) / toluene / 2 h / Heating

6: LiAlH₄ / tetrahydrofuran

7: 236.0 mg / imidazole / tetrahydrofuran / 6 h

8: camphorsulfonic acid, hydrogen / Pd-C / ethyl acetate; methanol / 2 h / 2585.74 Torr

9: 171.5 mg / NaHCO₃ / tetrahydrofuran; H₂O

10: 64 percent / triphenylphosphine, iodomethane, imidazole / toluene / 22 h / Heating

11: 96 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h

12: Dess-Martin reagent / CH₂Cl₂ / 0.5 h

With 1H-imidazole; dmap; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tributylphosphine; camphor-10-sulfonic acid; triphenylstannane; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; triphenylphosphine; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1021/jo982205k

upstream raw materials:

2,5-anhydro-1,3,4,6-tetradeoxy-6-<<(phenylmethoxy)carbonyl>amino>-D-xylo-hept-3-enitol

L-xylose

(2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol

phenyl 1-seleno-β-L-xylofuranoside

Downstream raw materials:

(S)-Benzyloxycarbonylamino-((2R,5S)-5-methyl-2,5-dihydro-furan-2-yl)-acetic acid