(3S,4R,5S)-3,4-O-isopropylidene-5-O-p-methoxybenzylhepta-1,6-diene-3,4,5-triol

Base Information

Chemical Name:(3S,4R,5S)-3,4-O-isopropylidene-5-O-p-methoxybenzylhepta-1,6-diene-3,4,5-triol
CAS No.:1053262-86-4
Molecular Formula:C₁₈H₂₄O₄
Molecular Weight:304.386
Hs Code.:

Synonyms:(3S,4R,5S)-3,4-O-isopropylidene-5-O-p-methoxybenzylhepta-1,6-diene-3,4,5-triol

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Chemical Property of (3S,4R,5S)-3,4-O-isopropylidene-5-O-p-methoxybenzylhepta-1,6-diene-3,4,5-triol

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Technology Process of (3S,4R,5S)-3,4-O-isopropylidene-5-O-p-methoxybenzylhepta-1,6-diene-3,4,5-triol

There total 8 articles about (3S,4R,5S)-3,4-O-isopropylidene-5-O-p-methoxybenzylhepta-1,6-diene-3,4,5-triol 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:

: 1779-49-3
Methyltriphenylphosphonium bromide

: (4R,5R)-5-[(S)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

: 1053262-86-4
(3S,4R,5S)-3,4-O-isopropylidene-5-O-p-methoxybenzylhepta-1,6-diene-3,4,5-triol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -20 ℃; for 1h;
DOI:10.1039/b207509a

Reference yield:

: 2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6
4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

: 1053262-86-4
(3S,4R,5S)-3,4-O-isopropylidene-5-O-p-methoxybenzylhepta-1,6-diene-3,4,5-triol

Guidance literature:: Multi-step reaction with 8 steps

1: t-BuOK / methanol / 3 h

2: pyridine / 2 h

3: 17.2 g / p-TsOH / acetone / 1 h

4: 80 percent / NaH / dimethylformamide / 48 h

5: 94 percent / TBAF / tetrahydrofuran / 0.75 h

6: 95 percent / imidazole; 1,4,5-triiodoimidazole; trphenylphosphine / toluene / 1 h / Heating

7: Zn / ethanol / 1.25 h / Heating

8: 152 mg / BuLi / hexane; tetrahydrofuran / 1 h / -20 °C

With pyridine; 1H-imidazole; n-butyllithium; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; 1,4,5-Triiodimidazol; triphenylphosphine; zinc; In tetrahydrofuran; methanol; ethanol; hexane; N,N-dimethyl-formamide; acetone; toluene; 8: Wittig reaction;
DOI:10.1039/b207509a

Reference yield:

: 503303-07-9
p-methoxyphenyl 3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

: 1053262-86-4
(3S,4R,5S)-3,4-O-isopropylidene-5-O-p-methoxybenzylhepta-1,6-diene-3,4,5-triol

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / NaH / dimethylformamide / 48 h

2: 94 percent / TBAF / tetrahydrofuran / 0.75 h

3: 95 percent / imidazole; 1,4,5-triiodoimidazole; trphenylphosphine / toluene / 1 h / Heating

4: Zn / ethanol / 1.25 h / Heating

5: 152 mg / BuLi / hexane; tetrahydrofuran / 1 h / -20 °C

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; 1,4,5-Triiodimidazol; triphenylphosphine; zinc; In tetrahydrofuran; ethanol; hexane; N,N-dimethyl-formamide; toluene; 5: Wittig reaction;
DOI:10.1039/b207509a