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

Base Information

Chemical Name:2-<(3R)-3-acetoxytetradecanamido>-6-O-<2-<(3R)-3-acetoxatetradecanamido>-3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-β-D-glucopyranosyl>-1,3-di-O-acetyl-2-deoxy-β-D-glucopyranose
CAS No.:90243-21-3
Molecular Formula:C₆₄H₉₇N₂O₂₂P
Molecular Weight:1277.45
Hs Code.:

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

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

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

There total 29 articles about 2-<(3R)-3-acetoxytetradecanamido>-6-O-<2-<(3R)-3-acetoxatetradecanamido>-3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-β-D-glucopyranosyl>-1,3-di-O-acetyl-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: 7.0%

: 85065-32-3
2-<(3R)-3-acetoxytetradecanamido>-3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-α-D-glucopyranosyl bromide

: 85065-30-1
2-<(3R)-3-acetoxytetradecanamido>-1,3-di-O-acetyl-2-deoxy-β-D-glucopyranose

: 85065-33-4,90243-21-3
2-<(3R)-3-acetoxytetradecanamido>-6-O-<2-<(3R)-3-acetoxatetradecanamido>-3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-β-D-glucopyranosyl>-1,3-di-O-acetyl-2-deoxy-β-D-glucopyranose

Guidance literature:: With 4 A molecular sieve; mercury(II) cyanide; In nitromethane; toluene; at 20 ℃; for 18h;
DOI:10.1016/0008-6215(83)88320-7

Reference yield: 7.0%

: 88862-76-4,90243-20-2
2'-<(2RS)-2-acetoxytridecyl>-3,6-di-O-acetyl-1,2-dideoxy-4-O-diphenylphosphono-α-D-glucopyranoso<2.1-d>-Δ²-oxazoline

: 85065-30-1
2-<(3RS)-3-acetoxytetradecanamido>-1,3-di-O-acetyl-2-deoxy-β-D-glucopyranose

: 90243-21-3
2-<(3RS)-3-acetoxytetradecanamido>-6-O-<2-<(3RS)-3-acetoxatetradecanamido>-3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-β-D-glucopyranosyl>-1,3-di-O-acetyl-2-deoxy-β-D-glucopyranose

Guidance literature:: With 2,6-lutidinium p-toluenesulfonate; In 1,2-dichloro-ethane; at 50 ℃; for 24h;
DOI:10.1039/P19840000275

Reference yield:

: 28715-21-1,3422-31-9
(R)-3-hydroxytetradecanoic acid

: 85065-33-4,90243-21-3
2-<(3R)-3-acetoxytetradecanamido>-6-O-<2-<(3R)-3-acetoxatetradecanamido>-3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-β-D-glucopyranosyl>-1,3-di-O-acetyl-2-deoxy-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 7 steps

1: Et₃N, NN-dicyclohexylcarbodi-imide / pyridine

2: NaOAc / 1 h / 100 °C

3: 41 percent / H₂ / 10percent palladium-charcoal / ethanol / 50 °C

4: 50 percent / pyridine / CH₂Cl₂ / -30 deg C -> room temperature, overnight

5: 85 percent / pyridine, 4-dimethylaminopyridine / benzene

6: 33percent HBr-AcOH, Ac₂O / CHCl₃ / 1 h / Ambient temperature

7: 7 percent / Hg(CN)2, 2-<(3R)-3-acetoxytetradecanamido>-1,3-di-O-acetyl-2-deoxy-β-D-glucopyranose / nitromethane; toluene / 72 h

With pyridine; dmap; hydrogen bromide; hydrogen; sodium acetate; mercury(II) cyanide; acetic anhydride; acetic acid; 2-<(3R)-3-acetoxytetradecanamido>-1,3-di-O-acetyl-2-deoxy-β-D-glucopyranose; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In pyridine; nitromethane; ethanol; dichloromethane; chloroform; toluene; benzene;
DOI:10.1039/P19840000275