3-O-<(R)-3-benzyloxytetradecanoyl>-2-deoxy-2-<(R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-α-D-glucopyranose

Base Information

• Chemical Name: 3-O-<(R)-3-benzyloxytetradecanoyl>-2-deoxy-2-<(R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-α-D-glucopyranose
• CAS No.: 102804-10-4
• Molecular Formula: C₆₀H₁₀₅NO₁₀
• Molecular Weight: 1000.49
• Mol file: 102804-10-4.mol

Synonyms:3-O-<(R)-3-benzyloxytetradecanoyl>-2-deoxy-2-<(R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-α-D-glucopyranose

Chemical Property of 3-O-<(R)-3-benzyloxytetradecanoyl>-2-deoxy-2-<(R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-α-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-<(R)-3-benzyloxytetradecanoyl>-2-deoxy-2-<(R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-α-D-glucopyranose

There total 14 articles about 3-O-<(R)-3-benzyloxytetradecanoyl>-2-deoxy-2-<(R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-α-D-glucopyranose 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: 64.0%

benzyl 3-O-<(R)-3-benzyloxytetradecanoyl>-2-deoxy-2-<(R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside (102804-09-1) → Hexadecanoic acid (R)-1-{[(4aR,7R,8R,8aS)-8-((R)-3-benzyloxy-tetradecanoyloxy)-6-hydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ylcarbamoyl]-methyl}-dodecyl ester (102804-10-4,103062-59-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol; under 750.06 Torr;

DOI:10.1016/S0008-6215(00)90445-2

Reference yield:

benzyl 3-O-<(R)-3-benzyloxytetradecanoyl>-2-deoxy-2-<(R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside (102804-09-1) → 3-O-<(R)-3-benzyloxytetradecanoyl>-2-deoxy-2-<(R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranose (103062-59-5) + 3-O-<(R)-3-benzyloxytetradecanoyl>-2-deoxy-2-<(R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-α-D-glucopyranose (102804-10-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol; at 30 ℃; for 38h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1248/cpb.35.4436

Reference yield:

benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (102794-17-2) → 3-O-<(R)-3-benzyloxytetradecanoyl>-2-deoxy-2-<(R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-α-D-glucopyranose (102804-10-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 5 h, 0 deg C; r.t., 12 h

2: 72 percent / dicyclohexylcarbodiimide, 4-methylaminopyridine / CH₂Cl₂ / 5 h, 0 deg C; r.t. 12 h

3: hydrogen / 10 percent Pd-on-carbon / tetrahydrofuran; ethanol / 38 h / 30 °C

4: acetic acid; tetrahydrofuran / 48 h / 45 °C

With 4-(Methylamino)pyridine; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetic acid;

DOI:10.1248/cpb.35.4436

upstream raw materials:

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

(R)-3-(hexadecanoyl)oxy-tetradecanoic acid

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

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

Downstream raw materials:

lipid Y

3-O-<(R)-3-benzyloxytetradecanoyl>-2-deoxy-2-<(R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-α-D-glucopyranosyl-1-phosphate