methyl 3,6-anhydro-2-benzamido-4-O-benzoyl-2-deoxy-5,7,8-tri-O-methyl-D-erythro-L-ido-octonate

Base Information

Chemical Name:methyl 3,6-anhydro-2-benzamido-4-O-benzoyl-2-deoxy-5,7,8-tri-O-methyl-D-erythro-L-ido-octonate
CAS No.:220588-00-1
Molecular Formula:C₂₆H₃₁NO₉
Molecular Weight:501.533
Hs Code.:

Synonyms:

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Chemical Property of methyl 3,6-anhydro-2-benzamido-4-O-benzoyl-2-deoxy-5,7,8-tri-O-methyl-D-erythro-L-ido-octonate

Chemical Property:

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Technology Process of methyl 3,6-anhydro-2-benzamido-4-O-benzoyl-2-deoxy-5,7,8-tri-O-methyl-D-erythro-L-ido-octonate

There total 13 articles about methyl 3,6-anhydro-2-benzamido-4-O-benzoyl-2-deoxy-5,7,8-tri-O-methyl-D-erythro-L-ido-octonate 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:

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

: 220588-00-1
methyl 3,6-anhydro-2-benzamido-4-O-benzoyl-2-deoxy-5,7,8-tri-O-methyl-D-erythro-L-ido-octonate

Guidance literature:: Multi-step reaction with 12 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: 42 percent / Bu₃SnH, AIBN / toluene / Heating

6: LiAlH₄ / tetrahydrofuran / 0 °C

7: imidazole / CH₂Cl₂ / 3.5 h

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

9: Et₃N, DMAP / CH₂Cl₂ / 24 h

10: 83 percent / Bu₄NF, pyridinium hydrochloride / tetrahydrofuran / 12 h

11: CrO₃, aq. H₂SO₄ / acetone / 1.5 h / 0 °C

12: diethyl ether

With 1H-imidazole; chromium(VI) oxide; dmap; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); sulfuric acid; 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; diethyl ether; dichloromethane; ethyl acetate; acetone; toluene;
DOI:10.1021/jo981435w

Reference yield:

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

: 220588-00-1
methyl 3,6-anhydro-2-benzamido-4-O-benzoyl-2-deoxy-5,7,8-tri-O-methyl-D-erythro-L-ido-octonate

Guidance literature:: Multi-step reaction with 11 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: 42 percent / Bu₃SnH, AIBN / toluene / Heating

5: LiAlH₄ / tetrahydrofuran / 0 °C

6: imidazole / CH₂Cl₂ / 3.5 h

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

8: Et₃N, DMAP / CH₂Cl₂ / 24 h

9: 83 percent / Bu₄NF, pyridinium hydrochloride / tetrahydrofuran / 12 h

10: CrO₃, aq. H₂SO₄ / acetone / 1.5 h / 0 °C

11: diethyl ether

With 1H-imidazole; chromium(VI) oxide; dmap; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); sulfuric acid; 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; diethyl ether; dichloromethane; ethyl acetate; acetone; toluene;
DOI:10.1021/jo981435w

Reference yield:

: 220587-66-6
phenyl 3,5,6-tri-O-methyl-1-seleno-β-D-glucofuranoside

: 220588-00-1
methyl 3,6-anhydro-2-benzamido-4-O-benzoyl-2-deoxy-5,7,8-tri-O-methyl-D-erythro-L-ido-octonate

Guidance literature:: Multi-step reaction with 9 steps

1: DCC, DMAP / CH₂Cl₂ / 12 h

2: 42 percent / Bu₃SnH, AIBN / toluene / Heating

3: LiAlH₄ / tetrahydrofuran / 0 °C

4: imidazole / CH₂Cl₂ / 3.5 h

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

6: Et₃N, DMAP / CH₂Cl₂ / 24 h

7: 83 percent / Bu₄NF, pyridinium hydrochloride / tetrahydrofuran / 12 h

8: CrO₃, aq. H₂SO₄ / acetone / 1.5 h / 0 °C

9: diethyl ether

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