methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranosiduronic acid methyl ester

Base Information

Chemical Name:methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranosiduronic acid methyl ester
CAS No.:1346418-01-6
Molecular Formula:C₁₇H₂₀O₈
Molecular Weight:352.341
Hs Code.:

Synonyms:

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Chemical Property of methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranosiduronic acid methyl ester

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Technology Process of methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranosiduronic acid methyl ester

There total 7 articles about methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranosiduronic acid methyl 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:

: methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranosiduronic acid

: 74-88-4
methyl iodide

: 1346418-01-6
methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranosiduronic acid methyl ester

Guidance literature:: With potassium carbonate; In acetonitrile; at 24 ℃; for 16h; Inert atmosphere;
DOI:10.1021/jo201673w

Reference yield:

: 1346417-98-8
methyl 2-O-acetyl-6-O-(tert-butyldimethylsilyl)-4-deoxy-β-D-ribohexopyranoside

: 1346418-01-6
methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranosiduronic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 0.83 h / 24 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 24 °C / Inert atmosphere

3: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 0.75 h / 24 °C

4: potassium carbonate / acetonitrile / 16 h / 24 °C / Inert atmosphere

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; potassium carbonate; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile; 1: Mitsunobu reaction;
DOI:10.1021/jo201673w

Reference yield:

: (2R,6S)-6-(tert-butyldimethylsilyloxymethyl)-2-methoxy-2,5-dihydropyran

: 1346418-01-6
methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranosiduronic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 16 h / 24 °C

2: pyridine; dmap / dichloromethane / 0.83 h / 24 °C / Inert atmosphere

3: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 0.83 h / 24 °C / Inert atmosphere

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 24 °C / Inert atmosphere

5: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 0.75 h / 24 °C

6: potassium carbonate / acetonitrile / 16 h / 24 °C / Inert atmosphere

With pyridine; dmap; osmium(VIII) oxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; potassium carbonate; 4-methylmorpholine N-oxide; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; acetone; toluene; acetonitrile; 3: Mitsunobu reaction;
DOI:10.1021/jo201673w