DL-3,7-O-Benzylidene-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol

Base Information

• Chemical Name: DL-3,7-O-Benzylidene-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol
• CAS No.: 77144-71-9
• Molecular Formula: C₁₄H₁₆O₄
• Molecular Weight: 248.279

Synonyms:DL-3,7-O-Benzylidene-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol

Chemical Property of DL-3,7-O-Benzylidene-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol

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Technology Process of DL-3,7-O-Benzylidene-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol

There total 7 articles about DL-3,7-O-Benzylidene-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol 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: 53.0%

benzaldehyde dimethyl acetal (1125-88-8) + DL-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol (77144-67-3) → DL-3,7-O-Benzylidene-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol (77144-71-9)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 60 ℃; for 1.5h;

DOI:10.1021/jo00156a012

Reference yield: 43.0%

benzaldehyde dimethyl acetal (1125-88-8) + DL-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol (77144-67-3) → (+/-)-(4aα,7α,8aβ,8β)-2-phenyl-4a,7,8,8a-tetrahydro-4H-1,3-benzodioxin-7,8-diol (77144-71-9,119066-23-8)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 60 ℃; for 1.5h; under 20 Torr;

DOI:10.1246/cl.1980.1559

Reference yield: 32.0%

(+/-)-(4aα,7α,8aβ,8β)-8-acetoxy-7-(tert-butyldimethylsilyloxy)-2-phenyl-4a,7,8,8a-tetrahydro-4H-benzo-1,3-dioxine → (+/-)-(4aα,7α,8aβ,8β)-2-phenyl-4a,7,8,8a-tetrahydro-4H-1,3-benzodioxin-7,8-diol (77144-71-9,119066-23-8) + (+/-)-(4aα,7α,8aβ,8β)-8-acetoxy-2-phenyl-4a,7,8,8a-tetrahydro-4H-benzo-1,3-dioxin-7-ol + (+/-)-(4aα,7α,8aβ,8β)-7-acetoxy-2-phenyl-4a,7,8,8a-tetrahydro-4H-benzo-1,3-dioxin-8-ol

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 1.5h;

DOI:10.1021/jo0300946

upstream raw materials:

benzaldehyde dimethyl acetal

DL-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol

DL-(1,3/2,4,6)-1,2,3-tri-O-acetyl-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol

DL-O-triacetyl-(1,3/2,4)-4-<(benzoyloxy)methyl>-5-cyclohexene-1,2,3-triol

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