(2R,4aR,8R,8aS)-8-Hydroxy-2-(4-methoxy-phenyl)-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-one

Base Information

• Chemical Name: (2R,4aR,8R,8aS)-8-Hydroxy-2-(4-methoxy-phenyl)-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-one
• CAS No.: 391611-27-1
• Molecular Formula: C₁₄H₁₆O₆
• Molecular Weight: 280.277

Synonyms:(2R,4aR,8R,8aS)-8-Hydroxy-2-(4-methoxy-phenyl)-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-one

Chemical Property of (2R,4aR,8R,8aS)-8-Hydroxy-2-(4-methoxy-phenyl)-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-one

Chemical Property:

Purity/Quality:

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Technology Process of (2R,4aR,8R,8aS)-8-Hydroxy-2-(4-methoxy-phenyl)-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-one

There total 3 articles about (2R,4aR,8R,8aS)-8-Hydroxy-2-(4-methoxy-phenyl)-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-one 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: 71.0%

(2R,4aR,8R,8aS)-2-(4-Methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-6,8-diol → (2R,4aR,8R,8aS)-8-Hydroxy-2-(4-methoxy-phenyl)-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-one (391611-27-1)

Guidance literature:

With bromine; sodium hydrogencarbonate; In 1,4-dioxane; water;

DOI:10.1016/S0040-4039(01)01763-4

Reference yield:

2-deoxy-D-arabino-hexopyranose (61-58-5,13299-15-5,13299-16-6,14215-77-1,14215-78-2,20789-85-9,23568-30-1,25494-04-6,34339-39-4,34339-40-7,34339-46-3,34339-47-4,114717-20-3,114717-21-4,137491-75-9,137491-76-0) → (2R,4aR,8R,8aS)-8-Hydroxy-2-(4-methoxy-phenyl)-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-one (391611-27-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / TsOH / dimethylformamide / 40 °C

2: 71 percent / Br₂; NaHCO₃ / dioxane; H₂O

With bromine; sodium hydrogencarbonate; toluene-4-sulfonic acid; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)01763-4

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (2R,4aR,8R,8aS)-8-Hydroxy-2-(4-methoxy-phenyl)-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-one (391611-27-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / TsOH / dimethylformamide / 40 °C

2: 71 percent / Br₂; NaHCO₃ / dioxane; H₂O

With bromine; sodium hydrogencarbonate; toluene-4-sulfonic acid; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)01763-4

upstream raw materials:

2-deoxy-D-arabino-hexopyranose

p-Anisaldehyde dimethyl acetal

Downstream raw materials:

(2R,4aR,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-one

4-(tert-butyl-diphenyl-silanyloxy)-pent-2-enoic acid (6-{5-[3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-6-methyl-4-methylene-tetrahydro-pyran-2-yl]-3-methyl-penta-2,4-dienyl}-2,5-dimethyl-tetrahydro-pyran-3-yl)-amide

tert-Butyl-[(2R,4aR,6S,8R,8aR)-6-methoxy-2-(4-methoxy-phenyl)-6-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-dimethyl-silane

tert-Butyl-[(2R,4aR,8R,8aR)-2-(4-methoxy-phenyl)-6-methylene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-dimethyl-silane

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