(4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid methyl ester

Base Information

Chemical Name:(4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid methyl ester
CAS No.:189238-19-5
Molecular Formula:C₁₆H₂₀O₇
Molecular Weight:324.331
Hs Code.:

Synonyms:(4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid methyl ester

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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 (4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid methyl ester

There total 2 articles about (4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic 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:

: 1125-88-8
benzaldehyde dimethyl acetal

: 85549-53-7,85549-51-5
(2R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 189238-19-5
(4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid methyl ester

Guidance literature:: With camphor-10-sulfonic acid; In N,N-dimethyl-formamide; at 60 ℃; for 12h;
DOI:10.1021/ja952265x

Reference yield:

: 29873-81-2
3-Desoxy-D-lyxo-heptulosansaeure

: 189238-19-5
(4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 60 percent / Dowex 50W-X₈ (H⁺) / 2 h / Heating

2: camphorsulfonic acid / dimethylformamide / 12 h / 60 °C

With Dowex 50W-X₈ (H⁺); camphor-10-sulfonic acid; In N,N-dimethyl-formamide;
DOI:10.1021/ja952265x

Reference yield:

: 189238-19-5
(4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid methyl ester

: {(2R,4R,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-methoxy-2-[(1R,2R)-2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-tetrahydro-pyran-4-yloxy}-acetic acid

Guidance literature:: Multi-step reaction with 5 steps

1: aq. LiOH / methanol / 2 h / Ambient temperature

2: 58 percent / HOBt, 4-methylmorpholine, EDC / dimethylformamide / 12 h / -20 - 25 °C

3: 53 percent / NaH, Bu₄NI / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 4 h

4: 90 percent / H₂ / 20percent Pd(OH)2/C / methanol / 8 h / 760 Torr / Ambient temperature

5: 76 percent / NaOH / 4 h / Ambient temperature

With 4-methyl-morpholine; lithium hydroxide; sodium hydroxide; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium dihydroxide; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/ja952265x