allyl 2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

Base Information

Chemical Name:allyl 2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
CAS No.:132831-89-1
Molecular Formula:C₃₄H₅₂FNO₉
Molecular Weight:637.787
Hs Code.:

Synonyms:allyl 2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

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Chemical Property of allyl 2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

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Technology Process of allyl 2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

There total 1 articles about allyl 2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-4,6-O-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: 43.0%

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

: 120927-34-6
(+/-)-threo-3-<(benzyloxycarbonyl)oxy>-2-fluorotetradecanoic acid

: 132760-32-8
allyl 2-<(2R,3S)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

: 132831-89-1
allyl 2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

Guidance literature:: With dicyclohexyl-carbodiimide; In dichloromethane; at 25 ℃; for 1h;
DOI:10.1248/cpb.40.333

Reference yield: 76.0%

: 132831-89-1
allyl 2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

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

: allyl 2-<(2S,3R)-3-(benzyloxycarbonyloxy)-2-fluorotetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanoyl>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

Guidance literature:: With triethylamine; In tetrahydrofuran; Ambient temperature;
DOI:10.1271/bbb.57.1526

Reference yield:

: 132831-89-1
allyl 2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

: 2-deoxy-4-O-diphenoxyphosphinyl-2-<(2S,3R)-2-fluoro-3-hydroxytetradecanamido>-3-O-<(3R)-3-hydroxytetradecanoyl>-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 6 steps

1: 76 percent / triethylamine / tetrahydrofuran / Ambient temperature

2: 96 percent / acetic acid / 0.5 h / 50 °C

3: 65 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / 25 °C

4: 99 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / 25 °C

5: 1.) hydrogen, 1,5-cyclooctadiene-bis(methyldiphenylphosphine)iridium hexafluorophosphate, 2.) iodine, pyridine, H₂O / 1.) THF, 25 deg C, 2 h, 2.) 25 deg C, 30 min

6: 56 percent / hydrogen / 10percent Pd on carbon / tetrahydrofuran / 3 h / 25 °C

With pyridine; dmap; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; water; hydrogen; iodine; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;
DOI:10.1271/bbb.57.1526