(S)-11-((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecanoic acid methyl ester

Base Information

Chemical Name:(S)-11-((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecanoic acid methyl ester
CAS No.:191807-05-3
Molecular Formula:C₂₃H₄₄O₇
Molecular Weight:432.598
Hs Code.:

Synonyms:(S)-11-((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecanoic acid methyl ester

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Chemical Property of (S)-11-((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecanoic acid methyl ester

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Technology Process of (S)-11-((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecanoic acid methyl ester

There total 1 articles about (S)-11-((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecanoic acid methyl ester 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:

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

: 191807-05-3
(S)-11-((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecanoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 97 percent / imidazole; DMAP / CH₂Cl₂ / 3 h / 20 °C

2.1: magnesium; I₂ / tetrahydrofuran / 2 h / Heating

2.2: 66 percent / CuI / tetrahydrofuran / 2.5 h / -78 - 20 °C

3.1: 90.5 percent / pyridine / 20 °C

4.1: 89.4 percent / Jones reagent / acetone / 1.5 h / 0 - 20 °C

5.1: 96.9 percent / BF₃*OEt₂ / 4 h / 40 °C

6.1: 65.7 percent / 4 Angstroem MS; BF₃*OEt₂ / CH₂Cl₂ / 1 h / -30 - 0 °C

7.1: NaOMe / methanol / 0.42 h / -15 °C

With pyridine; 1H-imidazole; dmap; jones reagent; 4 Angstroem MS; boron trifluoride diethyl etherate; iodine; sodium methylate; magnesium; In tetrahydrofuran; methanol; dichloromethane; acetone; 1.1: silylation / 2.1: Metallation / 2.2: Addition / 3.1: Acetylation / 4.1: Jones oxidation / 5.1: methanolysis / 6.1: glycosylation / 7.1: Deacetylation;
DOI:10.1021/jo9711450

Reference yield:

: 191807-05-3
(S)-11-((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecanoic acid methyl ester

: 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

Guidance literature:: Multi-step reaction with 2 steps

1: 154 mg / p-TsOH / acetone / 20 °C

2: 76.5 percent / 4 Angstroem MS; NIS; AgOTf / CH₂Cl₂; toluene / 0.5 h / -15 °C

With N-iodo-succinimide; 4 Angstroem MS; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; In dichloromethane; acetone; toluene; 1: Cyclization / 2: glycosylation;
DOI:10.1021/jo9711450

Reference yield:

: 191807-05-3
(S)-11-((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecanoic acid methyl ester

: (S)-1-(hydroxycarbonyl)pentadec-10-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside 1,2(B)-lactone

Guidance literature:: Multi-step reaction with 4 steps

1: 154 mg / p-TsOH / acetone / 20 °C

2: 76.5 percent / 4 Angstroem MS; NIS; AgOTf / CH₂Cl₂; toluene / 0.5 h / -15 °C

3: 91 percent / KOH / methanol; H₂O / 10 h / Heating

4: 11 percent / (PyS)2; Ph₃P / toluene / 182.4 h / 20 °C / Heating

With potassium hydroxide; N-iodo-succinimide; 4 Angstroem MS; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; triphenylphosphine; In methanol; dichloromethane; water; acetone; toluene; 1: Cyclization / 2: glycosylation / 3: Hydrolysis / 4: Cyclization;
DOI:10.1021/jo9711450