2-<(3R)-3-acetoxytetradecanamido>-1,3-di-O-acetyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranose

Base Information

• Chemical Name: 2-<(3R)-3-acetoxytetradecanamido>-1,3-di-O-acetyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranose
• CAS No.: 85065-29-8
• Molecular Formula: C₃₃H₄₉NO₁₀
• Molecular Weight: 619.753

Synonyms:2-<(3R)-3-acetoxytetradecanamido>-1,3-di-O-acetyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranose

Chemical Property of 2-<(3R)-3-acetoxytetradecanamido>-1,3-di-O-acetyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranose

Chemical Property:

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Technology Process of 2-<(3R)-3-acetoxytetradecanamido>-1,3-di-O-acetyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranose

There total 9 articles about 2-<(3R)-3-acetoxytetradecanamido>-1,3-di-O-acetyl-4,6-O-benzylidene-2-deoxy-β-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:

(R)-3-hydroxytetradecanoic acid (28715-21-1,3422-31-9) → 2-<(3R)-3-acetoxytetradecanamido>-1,3-di-O-acetyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranose (85065-29-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N, NN-dicyclohexylcarbodi-imide / pyridine

2: NaOAc / 1 h / 100 °C

With sodium acetate; triethylamine; dicyclohexyl-carbodiimide; In pyridine;

DOI:10.1039/P19840000275

Reference yield:

1,3-di-O-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranose hydrochloride (85065-28-7) → 2-<(3R)-3-acetoxytetradecanamido>-1,3-di-O-acetyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranose (85065-29-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N, NN-dicyclohexylcarbodi-imide / pyridine

2: NaOAc / 1 h / 100 °C

With sodium acetate; triethylamine; dicyclohexyl-carbodiimide; In pyridine;

DOI:10.1039/P19840000275

Reference yield:

1,3-di-O-acetyl-4,6-O-benzylidene-2-benzylideneamino-2-deoxy-β-D-glucopyranose (85065-27-6) → 2-<(3R)-3-acetoxytetradecanamido>-1,3-di-O-acetyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranose (85065-29-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / 5M HCl / acetone / 0.25 h / ice-bath

2: Et₃N, NN-dicyclohexylcarbodi-imide / pyridine

3: NaOAc / 1 h / 100 °C

With hydrogenchloride; sodium acetate; triethylamine; dicyclohexyl-carbodiimide; In pyridine; acetone;

DOI:10.1039/P19840000275

upstream raw materials:

acetic anhydride

(R)-3-hydroxytetradecanoic acid

benzaldehyde

2-benzylideneamino-2-deoxy-β-D-glucopyranose

Downstream raw materials:

Acetic acid (3aR,5R,6S,7R,7aR)-5-acetoxymethyl-6-(diphenoxy-phosphoryloxy)-2-((E)-tridec-1-enyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-7-yl ester

methyl 3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-2-<(E)-tetradec-2-enamido>-β-D-glucopyranoside

methyl 2-<(3RS)-3-acetoxytetradecanamido>-3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-β-D-glucopyranoside

2'-<(2RS)-2-acetoxytridecyl>-3,6-di-O-acetyl-1,2-dideoxy-4-O-diphenylphosphono-α-D-glucopyranoso<2.1-d>-Δ²-oxazoline

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