methyl (11S)-11-[[(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-[[(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoate
CAS No.:197916-04-4
Molecular Formula:C₃₉H₆₂O₁₂
Molecular Weight:722.914
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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

There total 38 articles about methyl (11S)-11-[[(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: 91.0%

: 180782-75-6
1-(methoxycarbonyl)pentadec-10(S)-yl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside

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

Guidance literature:: With potassium hydroxide; In methanol; for 24h; Heating;
DOI:10.1002/anie.199723441

Reference yield:

: 55362-80-6
9-bromononan-1-ol

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

Guidance literature:: Multi-step reaction with 10 steps

1: 97 percent / imidazole / 3 h / Ambient temperature

2: 1.) Mg, 2.) CuI / 1.) THF, reflux, 2 h, 2.) -78 deg C to r.t., 2.5 h

3: 91 percent / pyridine / 14 h / Ambient temperature

4: 89 percent / Jones reagent / acetone / 1.5 h / Ambient temperature

5: 97 percent / BF₃*OEt₂ / 4 h / 40 °C

6: 66 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / -15 °C

7: 1percent NaOMe / methanol / 25 h / -15 °C

8: p-TsOH / acetone / 14 h

9: 76 percent / NIS, AgOTf, MS 4A / CH₂Cl₂ / 0.5 h / -15 °C

10: 91 percent / aq. KOH / methanol / 24 h / Heating

With pyridine; 1H-imidazole; potassium hydroxide; N-iodo-succinimide; copper(l) iodide; jones reagent; boron trifluoride diethyl etherate; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; magnesium; In methanol; dichloromethane; acetone;
DOI:10.1002/anie.199723441

Reference yield:

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

: 197916-04-4
methyl (11S)-11-[[(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: 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

With pyridine; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; silver trifluoromethanesulfonate; caesium carbonate; toluene-4-sulfonic acid; 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;
DOI:10.1021/jo971413u