1,3,4,7-tetra-O-acetyl-2-O-benzoyl-(1,2,3,5/4)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol

Base Information

• Chemical Name: 1,3,4,7-tetra-O-acetyl-2-O-benzoyl-(1,2,3,5/4)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol
• CAS No.: 74522-85-3
• Molecular Formula: C₂₂H₂₆O₁₀
• Molecular Weight: 450.442

Synonyms:1,3,4,7-tetra-O-acetyl-2-O-benzoyl-(1,2,3,5/4)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol

Chemical Property of 1,3,4,7-tetra-O-acetyl-2-O-benzoyl-(1,2,3,5/4)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol

Chemical Property:

Purity/Quality:

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Technology Process of 1,3,4,7-tetra-O-acetyl-2-O-benzoyl-(1,2,3,5/4)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol

There total 2 articles about 1,3,4,7-tetra-O-acetyl-2-O-benzoyl-(1,2,3,5/4)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol 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: 49.0%

sodium benzoate (532-32-1) + tetra-O-acetyl-(1,3,5/2,4)-2-bromo-5-hydroxymethyl-1,3,4-cyclohexanetriol (74517-36-5,74560-67-1) → 1,3,4,7-tetra-O-acetyl-2-O-benzoyl-(1,2,3,5/4)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol (74522-85-3)

Guidance literature:

With 18-crown-6 ether; In dimethyl sulfoxide; at 115 - 120 ℃; for 48h;

DOI:10.1246/bcsj.53.1121

Reference yield:

endo-3-acetoxy-endo-5-acetoxymethyl-exo-2-bromo-7-oxabicyclo<2.2.1>heptane (69982-68-9,96291-84-8,115225-40-6) → 1,3,4,7-tetra-O-acetyl-2-O-benzoyl-(1,2,3,5/4)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol (74522-85-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 13 percent / conc. H₂SO₄ / acetic acid / 90 - 95 °C

2: 49 percent / 18-crown-6 / dimethylsulfoxide / 48 h / 115 - 120 °C

With 18-crown-6 ether; sulfuric acid; In acetic acid; dimethyl sulfoxide;

DOI:10.1246/bcsj.53.1121

Reference yield:

1,3,4,7-tetra-O-acetyl-2-O-benzoyl-(1,2,3,5/4)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol (74522-85-3) → (1R,2R,3S,4R,5R)-5-Hydroxymethyl-cyclohexane-1,2,3,4-tetraol (10226-73-0,16656-62-5,16802-98-5,52079-85-3,64625-68-9,74560-71-7,74561-03-8,74561-07-2,74561-10-7,86117-80-8,86117-81-9,86117-82-0,90694-07-8,94943-08-5,94943-09-6,95043-48-4,96647-89-1,97372-13-9,97372-19-5,97372-28-6,97372-30-0,102629-13-0,105017-74-1,105017-81-0,108867-09-0,109668-67-9,135820-00-7)

Guidance literature:

With sodium methylate; In methanol; for 0.5h; Heating;

DOI:10.1246/bcsj.53.1121

upstream raw materials:

sodium benzoate

tetra-O-acetyl-(1,3,5/2,4)-2-bromo-5-hydroxymethyl-1,3,4-cyclohexanetriol

endo-3-acetoxy-endo-5-acetoxymethyl-exo-2-bromo-7-oxabicyclo<2.2.1>heptane

Downstream raw materials:

(1R,2R,3S,4R,5R)-5-Hydroxymethyl-cyclohexane-1,2,3,4-tetraol

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