benzyl 2-<(R)-3-hexadecanoyloxytetradecanamido>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2-<(R)-3-hexadecanoyloxytetradecanamido>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
• CAS No.: 116429-32-4
• Molecular Formula: C₃₇H₅₅NO₇
• Molecular Weight: 625.846
• Mol file: 116429-32-4.mol

Synonyms:benzyl 2-<(R)-3-hexadecanoyloxytetradecanamido>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

Chemical Property of benzyl 2-<(R)-3-hexadecanoyloxytetradecanamido>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-<(R)-3-hexadecanoyloxytetradecanamido>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

There total 3 articles about benzyl 2-<(R)-3-hexadecanoyloxytetradecanamido>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 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: 73.0%

(R)-3-benzyloxytetradecanoic acid (87357-67-3) + benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (102794-17-2) → benzyl 2-<(R)-3-hexadecanoyloxytetradecanamido>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (116429-32-4)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; 5 h, 0 deg C; r.t., 18 h;

DOI:10.1248/cpb.35.4436

Reference yield:

benzyl 2-chloroacetamido-2-deoxy-β-D-glucopyranoside (13318-87-1) → benzyl 2-<(R)-3-hexadecanoyloxytetradecanamido>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (116429-32-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / p-toluenesulfonic acid / dimethylformamide / 12 h / Ambient temperature

2: 80 percent / 1.) pyridine; 2.) 5percent aqueous sodium hydroxide / 1.) 85-90 deg C, 1.5 h; 2.) 30 deg C, 16 h, methanol

3: 73 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 5 h, 0 deg C; r.t., 18 h

With pyridine; sodium hydroxide; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.35.4436

Reference yield:

benzyl 2-(chloroacetylamino)-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (104495-54-7) → benzyl 2-<(R)-3-hexadecanoyloxytetradecanamido>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (116429-32-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / 1.) pyridine; 2.) 5percent aqueous sodium hydroxide / 1.) 85-90 deg C, 1.5 h; 2.) 30 deg C, 16 h, methanol

2: 73 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 5 h, 0 deg C; r.t., 18 h

With pyridine; sodium hydroxide; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1248/cpb.35.4436

upstream raw materials:

(R)-3-benzyloxytetradecanoic acid

benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

benzyl 2-chloroacetamido-2-deoxy-β-D-glucopyranoside

benzyl 2-(chloroacetylamino)-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

Downstream raw materials:

benzyl 2-deoxy-3-O-<(R)-hexadecanoyloxytetradacanoyl>-2-<(R)-3-hydroxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside

benzyl 2-<(R)-3-hexadecanoyloxytetradecanamido>-2-deoxy-3-O-<(R)-hexadecanoyloxytetradacanoyl>-4,6-O-isopropylidene-β-D-glucopyranoside