4-methoxybenzyl 5-O-benzyl-6-cyano-6-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside

Base Information

• Chemical Name: 4-methoxybenzyl 5-O-benzyl-6-cyano-6-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside
• CAS No.: 1382059-98-4
• Molecular Formula: C₂₅H₂₉NO₆
• Molecular Weight: 439.508
• Mol file: 1382059-98-4.mol

Synonyms:4-methoxybenzyl 5-O-benzyl-6-cyano-6-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside

Chemical Property of 4-methoxybenzyl 5-O-benzyl-6-cyano-6-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-methoxybenzyl 5-O-benzyl-6-cyano-6-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside

There total 3 articles about 4-methoxybenzyl 5-O-benzyl-6-cyano-6-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside 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: 79.0%

4-methoxybenzyl 6-cyano-6-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside (1382059-96-2) + benzyl chloride (100-44-7) → 4-methoxybenzyl 5-O-benzyl-6-cyano-6-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside (1382059-98-4)

Guidance literature:

With silver(l) oxide; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ol3013638

Reference yield:

4-methoxybenzyl 5,6-anhydro-2,3-O-isopropylidene-α-D-mannofuranoside (201678-24-2) → 4-methoxybenzyl 5-O-benzyl-6-cyano-6-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside (1382059-98-4)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium chloride / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere

2: silver(l) oxide / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

With ammonium chloride; silver(l) oxide; In N,N-dimethyl-formamide;

DOI:10.1021/ol3013638

Reference yield:

2,3-O-isopropylidene-1-O-p-methoxybenzyl-α-D-mannofuranoside (164665-83-2) → 4-methoxybenzyl 5-O-benzyl-6-cyano-6-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside (1382059-98-4)

Guidance literature:

Multi-step reaction with 3 steps

1: triphenylphosphine; diethylazodicarboxylate / toluene / 16 h / Inert atmosphere; Reflux

2: ammonium chloride / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere

3: silver(l) oxide / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

With ammonium chloride; triphenylphosphine; silver(l) oxide; diethylazodicarboxylate; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol3013638

upstream raw materials:

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

4-methoxybenzyl 6-cyano-6-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside

benzyl chloride

2,3-O-isopropylidene-1-O-p-methoxybenzyl-α-D-mannofuranoside

Downstream raw materials:

4-methoxybenzyl 5-O-benzyl-6-deoxy-2,3-O-isopropylidene-6-(1H-tetrazol-5-yl)-α-D-mannofuranoside

(5S,6S,7R,8S)-8-O-benzyl-7-O-formyl-6,7,8,9-tetrahydro-5H-tetrazolo[1,5-a]azepine-5,6,7,8-tetrol