(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan-6-carbaldehyde

Base Information

Chemical Name:(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan-6-carbaldehyde
CAS No.:300678-40-4
Molecular Formula:C₁₇H₁₆O₆
Molecular Weight:316.31
Hs Code.:

Synonyms:(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan-6-carbaldehyde

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Chemical Property of (2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan-6-carbaldehyde

Chemical Property:

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Technology Process of (2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan-6-carbaldehyde

There total 9 articles about (2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan-6-carbaldehyde 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:

: 301346-52-1
(1S,2R)-4-hydroxy-3-[2,3-epoxy-1-(4-hydroxy-3-methoxyphenyl)propoxy]benzaldehyde

: 300678-40-4
(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan-6-carbaldehyde

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 1h;
DOI:10.1016/S0040-4039(00)00820-0

Reference yield:

: 1135-24-6,537-98-4
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

: 300678-40-4
(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan-6-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1.1: H₂SO₄ / 16 h / 90 °C

2.1: K₂CO₃ / dimethylformamide / 3 h / 160 °C

3.1: 88 percent / LiAlH₄ / tetrahydrofuran / 1 h / -10 °C

4.1: AD-mix-β; MeSO2NH2; H2O / 2-methyl-propan-2-ol / 20 h / 0 °C

5.1: NaH / tetrahydrofuran / 1 h / 20 °C

5.2: N-tosylimidazole / tetrahydrofuran / 2 h / 20 °C

6.1: DEAD; PPh₃ / 20 °C

7.1: H₂ / 5 percent Pd/C / ethyl acetate

8.1: K₂CO₃ / methanol / 0.5 h / 20 °C

With lithium aluminium tetrahydride; methanesulfonamide; AD-mix-β; sulfuric acid; water; hydrogen; sodium hydride; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Esterification / 2.1: Alkylation / 3.1: Reduction / 4.1: dihydroxylation / 5.1: Metallation / 5.2: Cyclization / 6.1: Etherification / 7.1: Hydrogenolysis / 8.1: Cyclization;
DOI:10.1016/S0957-4166(00)00234-2

Reference yield:

: 4049-39-2
4-benzyloxy-3-hydroxy-benzaldehyde

: 300678-40-4
(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan-6-carbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: DEAD; PPh₃ / 20 °C

2: H₂ / 5 percent Pd/C / ethyl acetate

3: K₂CO₃ / methanol / 0.5 h / 20 °C

With hydrogen; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In methanol; ethyl acetate; 1: Etherification / 2: Hydrogenolysis / 3: Cyclization;
DOI:10.1016/S0957-4166(00)00234-2