methyl (2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(4-methoxybenzyloxy)hex-5-enoic acid

Base Information

Chemical Name:methyl (2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(4-methoxybenzyloxy)hex-5-enoic acid
CAS No.:778640-57-6
Molecular Formula:C₁₇H₂₂O₆
Molecular Weight:322.358
Hs Code.:

Synonyms:methyl (2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(4-methoxybenzyloxy)hex-5-enoic acid

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Chemical Property of methyl (2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(4-methoxybenzyloxy)hex-5-enoic acid

Chemical Property:

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Technology Process of methyl (2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(4-methoxybenzyloxy)hex-5-enoic acid

There total 3 articles about methyl (2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(4-methoxybenzyloxy)hex-5-enoic acid 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

: 778640-57-6
methyl (2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(4-methoxybenzyloxy)hex-5-enoic acid

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; In water; dimethyl sulfoxide; at 20 ℃; for 1h;
DOI:10.1002/anie.200454192

Reference yield:

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

: 778640-57-6
methyl (2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(4-methoxybenzyloxy)hex-5-enoic acid

Guidance literature:: Multi-step reaction with 2 steps

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

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

With sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In 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

: 778640-57-6
methyl (2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(4-methoxybenzyloxy)hex-5-enoic acid

Guidance literature:: Multi-step reaction with 3 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

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