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

Base Information

• Chemical Name: DL-O-triacetyl-(1,3/2,4)-4-<(benzoyloxy)methyl>-5-cyclohexene-1,2,3-triol
• CAS No.: 77144-65-1
• Molecular Formula: C₂₀H₂₂O₈
• Molecular Weight: 390.39

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

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

Chemical Property:

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

There total 2 articles about DL-O-triacetyl-(1,3/2,4)-4-<(benzoyloxy)methyl>-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: 25.0%

sodium benzoate (532-32-1) + DL-(1,3/2,4,6)-1,2,3-tri-O-acetyl-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol (70838-35-6) → DL-O-triacetyl-(1,3/2,4)-4-<(benzoyloxy)methyl>-5-cyclohexene-1,2,3-triol (77144-65-1)

Guidance literature:

With lithium bromide; In N,N-dimethyl-formamide; at 100 - 105 ℃; for 20h;

DOI:10.1021/jo00156a012

Reference yield: 5.0%

sodium benzoate (532-32-1) + DL-(1,3/2,4,6)-1,2,3-tri-O-acetyl-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol (70838-35-6) → DL-(1,3/2)-1,2,3-tri-O-acetyl-4-methylene-5-cyclohexene-1,2,3-triol (74024-01-4) + DL-O-triacetyl-(1,3/2,4)-4-<(benzoyloxy)methyl>-5-cyclohexene-1,2,3-triol (77144-65-1) + C27H28O10 (77144-66-2)

Guidance literature:

With lithium bromide; In N,N-dimethyl-formamide; at 100 ℃; for 20h;

DOI:10.1246/cl.1980.1559

Reference yield: 80.0%

DL-O-triacetyl-(1,3/2,4)-4-<(benzoyloxy)methyl>-5-cyclohexene-1,2,3-triol (77144-65-1) → DL-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol (77144-67-3)

Guidance literature:

With sodium methylate; In methanol; for 1.5h; Ambient temperature;

DOI:10.1021/jo00156a012

upstream raw materials:

sodium benzoate

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

Downstream raw materials:

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

DL-3,4,5-tri-O-acetyl-1,2-anhydro-7-O-benzoyl-(1,2,4,6/3,5)-6-(hydroxymethyl)-1,2,3,4,5-cyclohexanepentol

DL-3,4,5-tri-O-acetyl-1,2-anhydro-7-O-benzoyl-(1,2,3,5/4,6)-6-(hydroxymethyl)-1,2,3,4,5-cyclohexanepentol

(+/-)-(4aα,7α,8aβ,8β)-2-phenyl-4a,7,8,8a-tetrahydro-4H-1,3-benzodioxin-7,8-diol

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