allyl 2-<(R)-3-benzyloxytetradecanamido>-3-O-<(R)-3-benzloxytetradecanoyl>-2-deoxy-4,6-isopropylidene-β-D-glucopyranoside

Base Information

Chemical Name:allyl 2-<(R)-3-benzyloxytetradecanamido>-3-O-<(R)-3-benzloxytetradecanoyl>-2-deoxy-4,6-isopropylidene-β-D-glucopyranoside
CAS No.:99519-07-0
Molecular Formula:C₅₄H₈₅NO₉
Molecular Weight:892.27
Hs Code.:

Synonyms:allyl 2-<(R)-3-benzyloxytetradecanamido>-3-O-<(R)-3-benzloxytetradecanoyl>-2-deoxy-4,6-isopropylidene-β-D-glucopyranoside

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Chemical Property of allyl 2-<(R)-3-benzyloxytetradecanamido>-3-O-<(R)-3-benzloxytetradecanoyl>-2-deoxy-4,6-isopropylidene-β-D-glucopyranoside

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Technology Process of allyl 2-<(R)-3-benzyloxytetradecanamido>-3-O-<(R)-3-benzloxytetradecanoyl>-2-deoxy-4,6-isopropylidene-β-D-glucopyranoside

There total 5 articles about allyl 2-<(R)-3-benzyloxytetradecanamido>-3-O-<(R)-3-benzloxytetradecanoyl>-2-deoxy-4,6-isopropylidene-β-D-glucopyranoside 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: 84.0%

: 99519-05-8
Allyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

: 99519-06-9
(R)-3-(benzyloxy)tetradecanoyl chloride

: 99519-07-0
allyl 2-<(R)-3-benzyloxytetradecanamido>-3-O-<(R)-3-benzloxytetradecanoyl>-2-deoxy-4,6-isopropylidene-β-D-glucopyranoside

Guidance literature:: With dmap; In pyridine; dichloromethane; for 15h; Ambient temperature;
DOI:10.1248/cpb.33.1760

Reference yield: 80.0%

: 99519-05-8
Allyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

: 87357-67-3
(R)-3-benzyloxytetradecanoic acid

: 99519-07-0
allyl 2-<(R)-3-benzyloxytetradecanamido>-3-O-<(R)-3-benzloxytetradecanoyl>-2-deoxy-4,6-isopropylidene-β-D-glucopyranoside

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; 5 h, 0 degC, room t., 12 h;
DOI:10.1248/cpb.35.1383

Reference yield:

: 72333-25-6
allyl 3,4,6-tri-O-acetyl-2-(chloroacetamido)-2-deoxy-β-D-glucopyranoside

: 99519-07-0
allyl 2-<(R)-3-benzyloxytetradecanamido>-3-O-<(R)-3-benzloxytetradecanoyl>-2-deoxy-4,6-isopropylidene-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / aq. NH₃ (28percent) / methanol / 12 h / Ambient temperature

2: 87 percent / TsOH / dimethylformamide / 2 h / Ambient temperature

3: 1.) pyridine; 2.) aq. NaOH (5percent) / 1.) 100 deg C, 2 h; 2.) CH₃OH, room temp., 1.5 h

4: 84 percent / dimethylaminopyridine / pyridine; CH₂Cl₂ / 15 h / Ambient temperature

With pyridine; dmap; ammonium hydroxide; sodium hydroxide; toluene-4-sulfonic acid; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.33.1760