(Z)-Octadec-9-enoic acid (S)-3-[(2S,4R,5S,6R)-4,5-bis-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-1-((Z)-octadec-9-enoyloxymethyl)-propyl ester

Base Information

Chemical Name:(Z)-Octadec-9-enoic acid (S)-3-[(2S,4R,5S,6R)-4,5-bis-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-1-((Z)-octadec-9-enoyloxymethyl)-propyl ester
CAS No.:845884-63-1
Molecular Formula:C₇₀H₁₀₈O₁₁
Molecular Weight:1125.62
Hs Code.:

(Z)-Octadec-9-enoic acid (S)-3-[(2S,4R,5S,6R)-4,5-bis-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-1-((Z)-octadec-9-enoyloxymethyl)-propyl ester

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Chemical Property of (Z)-Octadec-9-enoic acid (S)-3-[(2S,4R,5S,6R)-4,5-bis-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-1-((Z)-octadec-9-enoyloxymethyl)-propyl ester

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Technology Process of (Z)-Octadec-9-enoic acid (S)-3-[(2S,4R,5S,6R)-4,5-bis-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-1-((Z)-octadec-9-enoyloxymethyl)-propyl ester

There total 7 articles about (Z)-Octadec-9-enoic acid (S)-3-[(2S,4R,5S,6R)-4,5-bis-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-1-((Z)-octadec-9-enoyloxymethyl)-propyl 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: 85.0%

: 112-77-6
(Z)-9-octadecenoyl chloride

: (S)-4-[(4R,5S,6R)-4,5-Bis-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-butane-1,2-diol

: 845884-63-1
(Z)-Octadec-9-enoic acid (S)-3-[(2S,4R,5S,6R)-4,5-bis-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-1-((Z)-octadec-9-enoyloxymethyl)-propyl ester

Guidance literature:: With pyridine; dmap;
DOI:10.1021/jo040254t

Reference yield:

: 3-(2,2-dimethyl-[1,3]dioxolan-4-yl)propionic acid 2,3-bis(benzyloxy)-1-(benzyloxymethyl)pent-4-enyl ester

: 845884-63-1
(Z)-Octadec-9-enoic acid (S)-3-[(2S,4R,5S,6R)-4,5-bis-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-1-((Z)-octadec-9-enoyloxymethyl)-propyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: TiCl₄; TMEDA; Zn / PbCl₂ / CH₂Cl₂; tetrahydrofuran / 60 °C

2: second-generation Grubbs catalyst / toluene / 2 h / 60 °C

3: H₂ / Pd/C / ethanol; ethyl acetate / 6 h / 2844.31 Torr

4: NaH; Bu₄NI / dimethylformamide / 6 h / 0 - 20 °C

5: 88 percent / p-TsOH / methanol; CH₂Cl₂

6: 85 percent / 4-DMAP; pyridine

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; N,N,N,N,-tetramethylethylenediamine; hydrogen; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; zinc; palladium on activated charcoal; lead(II) chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo040254t

Reference yield:

: (2R,3S,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-[2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-3,4-dihydro-2H-pyran

: 845884-63-1
(Z)-Octadec-9-enoic acid (S)-3-[(2S,4R,5S,6R)-4,5-bis-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-1-((Z)-octadec-9-enoyloxymethyl)-propyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: H₂ / Pd/C / ethanol; ethyl acetate / 6 h / 2844.31 Torr

2: NaH; Bu₄NI / dimethylformamide / 6 h / 0 - 20 °C

3: 88 percent / p-TsOH / methanol; CH₂Cl₂

4: 85 percent / 4-DMAP; pyridine

With pyridine; dmap; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo040254t