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

Base Information

Chemical Name:3-O-<(R)-3-benzyloxytetradecanoyl>-2-deoxy-2-<(R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-α-D-glucopyranosyl-1-phosphate
CAS No.:102804-11-5
Molecular Formula:C₆₀H₁₀₆NO₁₃P
Molecular Weight:1080.47
Hs Code.:

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

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

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

There total 10 articles about 3-O-<(R)-3-benzyloxytetradecanoyl>-2-deoxy-2-<(R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-α-D-glucopyranosyl-1-phosphate 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:

: 93390-37-5
(R)-3-(hexadecanoyl)oxy-tetradecanoic acid

: 102804-11-5
3-O-<(R)-3-benzyloxytetradecanoyl>-2-deoxy-2-<(R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-α-D-glucopyranosyl-1-phosphate

Guidance literature:: Multi-step reaction with 5 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

5: 1.) 1.6 M n-butyllithium, dibenzylphosphorochloridate; 2.) hydrogen / 2.) 10 percent Pd-on-carbon / 1.) n-hexane, THF, 10 min., -50 deg C; 2.) 20 h, 50 atm, THF, n-hexane, 30-40 deg C

With 4-(Methylamino)pyridine; n-butyllithium; dibenzyl phosphochloridate; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetic acid;
DOI:10.1248/cpb.35.4436

Reference yield:

: 102794-17-2
benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

: 102804-11-5
3-O-<(R)-3-benzyloxytetradecanoyl>-2-deoxy-2-<(R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-α-D-glucopyranosyl-1-phosphate

Guidance literature:: Multi-step reaction with 5 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

5: 1.) 1.6 M n-butyllithium, dibenzylphosphorochloridate; 2.) hydrogen / 2.) 10 percent Pd-on-carbon / 1.) n-hexane, THF, 10 min., -50 deg C; 2.) 20 h, 50 atm, THF, n-hexane, 30-40 deg C

With 4-(Methylamino)pyridine; n-butyllithium; dibenzyl phosphochloridate; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetic acid;
DOI:10.1248/cpb.35.4436

Reference yield:

: 102804-08-0
benzyl 2-deoxy-2-<(3R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside

: 102804-11-5
3-O-<(R)-3-benzyloxytetradecanoyl>-2-deoxy-2-<(R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-α-D-glucopyranosyl-1-phosphate

Guidance literature:: Multi-step reaction with 4 steps

1: 72 percent / dicyclohexylcarbodiimide, 4-methylaminopyridine / CH₂Cl₂ / 5 h, 0 deg C; r.t. 12 h

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

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

4: 1.) 1.6 M n-butyllithium, dibenzylphosphorochloridate; 2.) hydrogen / 2.) 10 percent Pd-on-carbon / 1.) n-hexane, THF, 10 min., -50 deg C; 2.) 20 h, 50 atm, THF, n-hexane, 30-40 deg C

With 4-(Methylamino)pyridine; n-butyllithium; dibenzyl phosphochloridate; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetic acid;
DOI:10.1248/cpb.35.4436