Benzoic acid (2R,3S,4S,5R)-2-((R)-1-benzoylamino-2-hydroxy-ethyl)-5-((R)-1,2-dimethoxy-ethyl)-4-methoxy-tetrahydro-furan-3-yl ester

Base Information

Chemical Name:Benzoic acid (2R,3S,4S,5R)-2-((R)-1-benzoylamino-2-hydroxy-ethyl)-5-((R)-1,2-dimethoxy-ethyl)-4-methoxy-tetrahydro-furan-3-yl ester
CAS No.:220587-99-5
Molecular Formula:C₂₅H₃₁NO₈
Molecular Weight:473.523
Hs Code.:

Synonyms:Benzoic acid (2R,3S,4S,5R)-2-((R)-1-benzoylamino-2-hydroxy-ethyl)-5-((R)-1,2-dimethoxy-ethyl)-4-methoxy-tetrahydro-furan-3-yl ester

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Chemical Property of Benzoic acid (2R,3S,4S,5R)-2-((R)-1-benzoylamino-2-hydroxy-ethyl)-5-((R)-1,2-dimethoxy-ethyl)-4-methoxy-tetrahydro-furan-3-yl ester

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Technology Process of Benzoic acid (2R,3S,4S,5R)-2-((R)-1-benzoylamino-2-hydroxy-ethyl)-5-((R)-1,2-dimethoxy-ethyl)-4-methoxy-tetrahydro-furan-3-yl ester

There total 11 articles about Benzoic acid (2R,3S,4S,5R)-2-((R)-1-benzoylamino-2-hydroxy-ethyl)-5-((R)-1,2-dimethoxy-ethyl)-4-methoxy-tetrahydro-furan-3-yl 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: 81.0%

: 220587-97-3
Benzoic acid (2R,3S,4S,5R)-2-[(R)-1-benzoylamino-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-((R)-1,2-dimethoxy-ethyl)-4-methoxy-tetrahydro-furan-3-yl ester

: 220587-99-5
Benzoic acid (2R,3S,4S,5R)-2-((R)-1-benzoylamino-2-hydroxy-ethyl)-5-((R)-1,2-dimethoxy-ethyl)-4-methoxy-tetrahydro-furan-3-yl ester

Guidance literature:: With tetrabutyl ammonium fluoride; pyridine hydrochloride; In tetrahydrofuran;
DOI:10.1021/jo981435w

Reference yield:

: 28436-51-3
3,5,6-tri-O-methyl-D-glucofuranose

: 220587-99-5
Benzoic acid (2R,3S,4S,5R)-2-((R)-1-benzoylamino-2-hydroxy-ethyl)-5-((R)-1,2-dimethoxy-ethyl)-4-methoxy-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1: pyridine / 14 h

2: 85 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / 0 °C

3: 96 percent / K₂CO₃ / tetrahydrofuran; methanol / 0.25 h

4: DCC, DMAP / CH₂Cl₂ / 12 h

5: 40 percent / Bu₃SnH, AIBN / toluene / Heating

6: LiAlH₄ / tetrahydrofuran / 0 °C

7: imidazole / CH₂Cl₂

8: camphorsulfonic acid, H₂ / Pd-C / ethyl acetate; methanol / 2 h / 2585.74 Torr

9: Et₃N, DMAP / CH₂Cl₂

10: 81 percent / Bu₄NF, pyridinium hydrochloride / tetrahydrofuran

With 1H-imidazole; dmap; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; pyridine hydrochloride; potassium carbonate; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo981435w

Reference yield:

: 1,2-di-O-acetyl-3,5,6-tri-O-methyl-α,β-D-glucofuranose

: 220587-99-5
Benzoic acid (2R,3S,4S,5R)-2-((R)-1-benzoylamino-2-hydroxy-ethyl)-5-((R)-1,2-dimethoxy-ethyl)-4-methoxy-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 85 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / 0 °C

2: 96 percent / K₂CO₃ / tetrahydrofuran; methanol / 0.25 h

3: DCC, DMAP / CH₂Cl₂ / 12 h

4: 40 percent / Bu₃SnH, AIBN / toluene / Heating

5: LiAlH₄ / tetrahydrofuran / 0 °C

6: imidazole / CH₂Cl₂

7: camphorsulfonic acid, H₂ / Pd-C / ethyl acetate; methanol / 2 h / 2585.74 Torr

8: Et₃N, DMAP / CH₂Cl₂

9: 81 percent / Bu₄NF, pyridinium hydrochloride / tetrahydrofuran

With 1H-imidazole; dmap; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; pyridine hydrochloride; potassium carbonate; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo981435w