methyl (11S)-11-[[(3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoate

Base Information

Chemical Name:methyl (11S)-11-[[(3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoate
CAS No.:197916-06-6
Molecular Formula:C₄₁H₆₄O₁₃
Molecular Weight:764.951
Hs Code.:

Synonyms:methyl (11S)-11-[[(3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoate

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Chemical Property of methyl (11S)-11-[[(3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoate

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Technology Process of methyl (11S)-11-[[(3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoate

There total 21 articles about methyl (11S)-11-[[(3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoate 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: 80.0%

: 108-24-7
acetic anhydride

: 197916-04-4
methyl (11S)-11-[[(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoate

: 197916-06-6
methyl (11S)-11-[[(3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoate

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 0.833333h;
DOI:10.1021/jo971413u

Reference yield:

: 127000-09-3
benzyl α-D-fucopyranoside

: 197916-06-6
methyl (11S)-11-[[(3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoate

Guidance literature:: Multi-step reaction with 9 steps

1: 87 percent / p-TsOH*H₂O / acetone / 19 h

2: 96 percent / pyridine / 18 h / 70 °C

3: 84 percent / H₂ / Pd(OH)2 / ethyl acetate / 120 h / 2585.74 Torr

4: Cs₂CO₃ / CH₂Cl₂ / 12 h

5: 79 percent / TMSOTf / CH₂Cl₂ / 0.92 h

6: 96 percent / NaOMe / methanol; methyl acetate / 10 h

7: 84 percent / AgOTf / CH₂Cl₂ / 40 h

8: 84 percent / NaOMe / methyl acetate; methanol / 2 h

9: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 0.83 h

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; silver trifluoromethanesulfonate; caesium carbonate; toluene-4-sulfonic acid; triethylamine; palladium dihydroxide; In methanol; dichloromethane; acetic acid methyl ester; ethyl acetate; acetone; 1: Cyclization / 2: Acylation / 3: Hydrogenolysis / 4: Addition / 5: glycosylation / 6: deacylation / 7: glycosylation / 8: Deacetylation / 9: Acetylation;
DOI:10.1021/jo971413u

Reference yield:

: 126900-97-8
benzyl 6-deoxy-3,4-O-isopropylidene-6-phenylthio-α-D-galactopyranoside

: 197916-06-6
methyl (11S)-11-[[(3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoate

Guidance literature:: Multi-step reaction with 8 steps

1: 96 percent / pyridine / 18 h / 70 °C

2: 84 percent / H₂ / Pd(OH)2 / ethyl acetate / 120 h / 2585.74 Torr

3: Cs₂CO₃ / CH₂Cl₂ / 12 h

4: 79 percent / TMSOTf / CH₂Cl₂ / 0.92 h

5: 96 percent / NaOMe / methanol; methyl acetate / 10 h

6: 84 percent / AgOTf / CH₂Cl₂ / 40 h

7: 84 percent / NaOMe / methyl acetate; methanol / 2 h

8: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 0.83 h

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; silver trifluoromethanesulfonate; caesium carbonate; triethylamine; palladium dihydroxide; In methanol; dichloromethane; acetic acid methyl ester; ethyl acetate; 1: Acylation / 2: Hydrogenolysis / 3: Addition / 4: glycosylation / 5: deacylation / 6: glycosylation / 7: Deacetylation / 8: Acetylation;
DOI:10.1021/jo971413u