(3S,4R)-3,4-isopropylidene-5-p-methoxybenzyl-1,3,4,5-tetrahydroxy-2-pentanone

Base Information

Chemical Name:(3S,4R)-3,4-isopropylidene-5-p-methoxybenzyl-1,3,4,5-tetrahydroxy-2-pentanone
CAS No.:267873-90-5
Molecular Formula:C₁₆H₂₂O₆
Molecular Weight:310.347
Hs Code.:

Synonyms:(3S,4R)-3,4-isopropylidene-5-p-methoxybenzyl-1,3,4,5-tetrahydroxy-2-pentanone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4R)-3,4-isopropylidene-5-p-methoxybenzyl-1,3,4,5-tetrahydroxy-2-pentanone

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Technology Process of (3S,4R)-3,4-isopropylidene-5-p-methoxybenzyl-1,3,4,5-tetrahydroxy-2-pentanone

There total 10 articles about (3S,4R)-3,4-isopropylidene-5-p-methoxybenzyl-1,3,4,5-tetrahydroxy-2-pentanone 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%

: 267873-89-2
(3R,4R)-1-acetyl-3,4-isopropylidene-5-p-methoxybenzyl-1,3,4,5-tetrahydroxy-2-pentanone

: 267873-90-5
(3S,4R)-3,4-isopropylidene-5-p-methoxybenzyl-1,3,4,5-tetrahydroxy-2-pentanone

Guidance literature:: With Candida antarctica lipase; ethanol; In di-isopropyl ether; at 20 ℃; for 15h;
DOI:10.1139/v99-252

Reference yield: 67.0%

: 67-64-1
acetone

: 289894-70-8
(3S,4R)-5-p-methoxybenzyloxy-1,3,4-trihydroxy-2-pentanone

: 267873-90-5
(3S,4R)-3,4-isopropylidene-5-p-methoxybenzyl-1,3,4,5-tetrahydroxy-2-pentanone

Guidance literature:: With 4 Angsteroem MS; toluene-4-sulfonic acid; for 5h;
DOI:10.1021/jo991989e

Reference yield:

: 14289-62-4
1-(allyloxymethyl)-4-methoxybenzene

: 267873-90-5
(3S,4R)-3,4-isopropylidene-5-p-methoxybenzyl-1,3,4,5-tetrahydroxy-2-pentanone

Guidance literature:: Multi-step reaction with 3 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: 647 mg / Me₂S / CH₂Cl₂ / 3 h / -78 - 20 °C

2.1: FDP aldolase; 1N NaOH / H₂O; dimethylformamide / 72 h / 20 °C / pH 6.8

2.2: 65 percent / 1N HCl; acid phosphatase / H₂O; dimethylformamide / 24 h / 20 °C / pH 4.8

3.1: 67 percent / p-TsOH; 4 Angsteroem MS / 5 h

With sodium hydroxide; 4 Angsteroem MS; FDP aldolase; toluene-4-sulfonic acid; ozone; In dichloromethane; water; N,N-dimethyl-formamide; 1.1: ozonolysis / 1.2: Decomposition / 2.1: Addition / 2.2: Hydrolysis / 3.1: Cyclization;
DOI:10.1021/jo991989e