methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranoside

Base Information

• Chemical Name: methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranoside
• CAS No.: 1346418-00-5
• Molecular Formula: C₁₆H₂₀O₇
• Molecular Weight: 324.331
• Mol file: 1346418-00-5.mol

Synonyms:methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranoside

Chemical Property of methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranoside

There total 5 articles about methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranoside 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: 94.0%

methyl 2-O-acetyl-3-O-benzoyl-6-O-(tert-butyldimethylsilyl)-4-deoxy-β-D-xylohexopyranoside (1346417-99-9) → methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranoside (1346418-00-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 24 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jo201673w

Reference yield:

methyl 2-O-acetyl-6-O-(tert-butyldimethylsilyl)-4-deoxy-β-D-ribohexopyranoside (1346417-98-8) → methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranoside (1346418-00-5)

Guidance literature:

Multi-step reaction with 2 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

With di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triphenylphosphine; In tetrahydrofuran; toluene; 1: Mitsunobu reaction;

DOI:10.1021/jo201673w

Reference yield:

(2R,6S)-6-(tert-butyldimethylsilyloxymethyl)-2-methoxy-2,5-dihydropyran → methyl 2-O-acetyl-3-O-benzoyl-4-deoxy-β-D-xylohexopyranoside (1346418-00-5)

Guidance literature:

Multi-step reaction with 4 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

With pyridine; dmap; osmium(VIII) oxide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; acetone; toluene; 3: Mitsunobu reaction;

DOI:10.1021/jo201673w

upstream raw materials:

methyl 6-O-(tert-butyldimethylsilyl)-4-deoxy-β-D-ribohexopyranoside

methyl 2-O-acetyl-6-O-(tert-butyldimethylsilyl)-4-deoxy-β-D-ribohexopyranoside

methyl 2-O-acetyl-3-O-benzoyl-6-O-(tert-butyldimethylsilyl)-4-deoxy-β-D-xylohexopyranoside

1-methoxybuta-1,3-diene

Downstream raw materials:

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