(2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic acid methyl ester

Base Information

Chemical Name:(2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic acid methyl ester
CAS No.:778640-38-3
Molecular Formula:C₁₈H₂₄O₆
Molecular Weight:336.385
Hs Code.:

Synonyms:(2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic acid methyl ester

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Chemical Property of (2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic acid methyl ester

Chemical Property:

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Technology Process of (2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic acid methyl ester

There total 4 articles about (2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic 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:

: 778640-51-0
(2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenal

: 778640-38-3
(2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: NaClO₂; NaH₂PO₄ / dimethylsulfoxide; H₂O / 1 h / 20 °C

2: 2.61 g / diethyl ether; methanol / 0.5 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; In methanol; diethyl ether; water; dimethyl sulfoxide;
DOI:10.1055/s-2007-965893

Reference yield:

: 778640-41-8
(2R,3S,4R)-2,3-O-isopropylidene-4-(p-methoxybenzyloxy)-5-hexene-1,2,3-triol

: 778640-38-3
(2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / oxalyl chloride; DMSO; i-Pr₂NEt / CH₂Cl₂ / 1 h / -78 - 0 °C

2: NaClO₂; NaH₂PO₄ / dimethylsulfoxide; H₂O / 1 h / 20 °C

3: 2.61 g / diethyl ether; methanol / 0.5 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; 1: Swern oxidation;
DOI:10.1055/s-2007-965893

Reference yield:

: 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-D-arabinose

: 778640-38-3
(2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: t-BuOK / benzene / 3 h / Heating

1.2: 86 percent / benzene; tetrahydrofuran / 1 h / Heating

2.1: 95 percent / oxalyl chloride; DMSO; i-Pr₂NEt / CH₂Cl₂ / 1 h / -78 - 0 °C

3.1: NaClO₂; NaH₂PO₄ / dimethylsulfoxide; H₂O / 1 h / 20 °C

4.1: 2.61 g / diethyl ether; methanol / 0.5 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; potassium tert-butylate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; benzene; 1.1: Wittig olefination / 1.2: Wittig olefination / 2.1: Swern oxidation;
DOI:10.1055/s-2007-965893