N-[(R)-3-(benzyloxy)tetradecanoyl]-4,6-O-isopropylidene-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

Base Information

Chemical Name:N-[(R)-3-(benzyloxy)tetradecanoyl]-4,6-O-isopropylidene-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine
CAS No.:177085-90-4
Molecular Formula:C₅₈H₁₀₁NO₁₀
Molecular Weight:972.441
Hs Code.:

Synonyms:N-[(R)-3-(benzyloxy)tetradecanoyl]-4,6-O-isopropylidene-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

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Chemical Property of N-[(R)-3-(benzyloxy)tetradecanoyl]-4,6-O-isopropylidene-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

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Technology Process of N-[(R)-3-(benzyloxy)tetradecanoyl]-4,6-O-isopropylidene-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

There total 12 articles about N-[(R)-3-(benzyloxy)tetradecanoyl]-4,6-O-isopropylidene-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine 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: 67.0%

: 87357-76-4
(R)-3-(dodecanoyloxy)tetradecanoic acid

: 177085-89-1
N-[(R)-3-(benzyloxy)tetradecanoyl]-4,6-O-isopropylidene-β-D-glucopyranosylamine

: 177085-90-4
N-[(R)-3-(benzyloxy)tetradecanoyl]-4,6-O-isopropylidene-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 25 ℃; for 1h;
DOI:10.1246/cl.1996.735

Reference yield:

: 604-69-3
β-D-glucose pentaacetate

: 177085-90-4
N-[(R)-3-(benzyloxy)tetradecanoyl]-4,6-O-isopropylidene-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / trimethylsilyl azide, SnCl₄ / CH₂Cl₂ / 0.5 h / 25 °C

2: 44 percent / H₂ / Pd(OH)2/C / tetrahydrofuran; H₂O / 25 °C

3: 84 percent / Et₃N / CH₂Cl₂ / 0.5 h / 25 °C

4: NaOMe / methanol / 0.5 h / 25 °C

5: pyridium p-toluenesulfonate / dimethylformamide / 3 h / 25 °C

6: 67 percent / DMAP, DCC / dimethylformamide / 1 h / 25 °C

With dmap; pyridium para-toluenesulfonate; trimethylsilylazide; hydrogen; sodium methylate; tin(IV) chloride; triethylamine; dicyclohexyl-carbodiimide; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1246/cl.1996.735

Reference yield:

: 13992-25-1
1-azido-1-deoxy-β-D-glucopyranoside tetraacetate

: 177085-90-4
N-[(R)-3-(benzyloxy)tetradecanoyl]-4,6-O-isopropylidene-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

Guidance literature:: Multi-step reaction with 5 steps

1: 44 percent / H₂ / Pd(OH)2/C / tetrahydrofuran; H₂O / 25 °C

2: 84 percent / Et₃N / CH₂Cl₂ / 0.5 h / 25 °C

3: NaOMe / methanol / 0.5 h / 25 °C

4: pyridium p-toluenesulfonate / dimethylformamide / 3 h / 25 °C

5: 67 percent / DMAP, DCC / dimethylformamide / 1 h / 25 °C

With dmap; pyridium para-toluenesulfonate; hydrogen; sodium methylate; triethylamine; dicyclohexyl-carbodiimide; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1246/cl.1996.735