DL-1,2,3-tri-O-acetyl-(1,3/2,4)-4-bromo-6-methylene-1,2,3-cyclohexenetriol

Base Information

• Chemical Name: DL-1,2,3-tri-O-acetyl-(1,3/2,4)-4-bromo-6-methylene-1,2,3-cyclohexenetriol
• CAS No.: 74023-99-7
• Molecular Formula: C₁₃H₁₇BrO₆
• Molecular Weight: 349.178

Synonyms:DL-1,2,3-tri-O-acetyl-(1,3/2,4)-4-bromo-6-methylene-1,2,3-cyclohexenetriol

Chemical Property of DL-1,2,3-tri-O-acetyl-(1,3/2,4)-4-bromo-6-methylene-1,2,3-cyclohexenetriol

Chemical Property:

Purity/Quality:

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Technology Process of DL-1,2,3-tri-O-acetyl-(1,3/2,4)-4-bromo-6-methylene-1,2,3-cyclohexenetriol

There total 2 articles about DL-1,2,3-tri-O-acetyl-(1,3/2,4)-4-bromo-6-methylene-1,2,3-cyclohexenetriol 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: 60.0%

DL-(1,3/2,4,6)-1,2,3-tri-O-acetyl-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol (70838-35-6) → DL-1,2,3-tri-O-acetyl-(1,3/2,4)-4-bromo-6-methylene-1,2,3-cyclohexenetriol (74023-99-7)

Guidance literature:

With silver fluoride; In pyridine; at 20 ℃; for 20h;

DOI:10.1246/bcsj.53.455

Reference yield:

acetic anhydride (108-24-7) + 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-1,2,3-tri-O-acetyl-(1,3/2,4)-4-bromo-6-methylene-1,2,3-cyclohexenetriol (74023-99-7) + DL-1,2,3-tri-O-acetyl-(1,3/2,4,6)-6-acetoxymethyl-4-bromo-1,2,3-cyclohexanetriol (70878-41-0) + DL-penta-O-acetyl-(1,4/2,3,5)-5-(hydroxymethyl)-1,2,3,4-cyclohexanetetrol (74561-02-7)

Guidance literature:

With sodium acetate; Yield given. Multistep reaction. Yields of byproduct given; 1.) 90percent aqueous 2-methoxyethanol, 80 deg C, 40h; 2.) pyridine, room temp., overnight;

DOI:10.1021/jo00156a012

Reference yield: 60.0%

DL-1,2,3-tri-O-acetyl-(1,3/2,4)-4-bromo-6-methylene-1,2,3-cyclohexenetriol (74023-99-7) → tri-O-acetyl-(1,3/2)-4-methylene-1,2,3-cyclohexanetriol

Guidance literature:

With azobisisobutyronitrile; tri-n-butyl-tin hydride; In toluene; at 80 ℃; for 0.5h;

DOI:10.1246/bcsj.53.455

upstream raw materials:

acetic anhydride

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

Downstream raw materials:

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

D,L-(1,3,5/2,4)-1-C-acetoxymethyl-2,3,4-tri-O-acetyl-5-bromo-1,2,3,4-cyclohexanetetrol

DL-(1,3/2)-1,2,3-tri-O-acetyl-4-methylene-5-cyclohexene-1,2,3-triol

DL-2,3,4,7-tetra-O-acetyl-(1,2,4/3)-1-C-hydroxymethyl-5-cyclohexene-1,2,3,4-tetrol

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