methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose

Base Information

• Chemical Name: methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose
• CAS No.: 497234-42-1
• Molecular Formula: C₁₇H₂₂O₆
• Molecular Weight: 322.358
• Mol file: 497234-42-1.mol

Synonyms:methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose

Chemical Property of methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose

There total 4 articles about methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose 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 6-O-benzyl-2,3-O-isopropylidene-α-D-mannofuranoside (161365-10-2) → methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose (497234-42-1)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 ℃; for 8h;

DOI:10.1002/1522-2675(200209)85:9<2608::AID-HLCA2608>3.0.CO;2-F

Reference yield:

methyl 2,3-O-isopropylidene-α-D-mannofuranoside (27954-10-5) → methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose (497234-42-1)

Guidance literature:

Multi-step reaction with 3 steps

1: PPh₃; DEAD / toluene / Heating

2: NaH / 1,2-dimethoxy-ethane; various solvent(s) / 60 °C

3: PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

With 4 A molecular sieve; sodium hydride; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; In 1,2-dimethoxyethane; dichloromethane; toluene;

DOI:10.1016/S0008-6215(03)00235-0

Reference yield:

methyl 5,6-anhydro-2,3-O-isopropylidene-α-D-mannofuranoside (220051-10-5) → methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose (497234-42-1)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / 1,2-dimethoxy-ethane; various solvent(s) / 60 °C

2: PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

With 4 A molecular sieve; sodium hydride; pyridinium chlorochromate; In 1,2-dimethoxyethane; dichloromethane;

DOI:10.1016/S0008-6215(03)00235-0

upstream raw materials:

methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-mannofuranoside

methyl 2,3-O-isopropylidene-α-D-mannofuranoside

methyl 5,6-anhydro-2,3-O-isopropylidene-α-D-mannofuranoside

methyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannofuranoside

Downstream raw materials:

methyl (5R)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-α-D-mannofuranoside

methyl (5S)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-β-L-gulofuranoside

methyl (5S)-6-O-benzyl-5-(dimethoxyphosphinyl)-2,3-O-isopropylidene-α-D-lyxo-hexofuranoside

methyl (5R)-6-O-benzyl-5-(dimethoxyphosphinyl)-2,3-O-isopropylidene-α-D-lyxo-hexofuranoside