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

Base Information

• Chemical Name: DL-(1,3/2,4,6)-1,2,3-tri-O-acetyl-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol
• CAS No.: 70838-35-6
• Molecular Formula: C₁₃H₁₈Br₂O₆
• Molecular Weight: 430.09
• Mol file: 70838-35-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about DL-(1,3/2,4,6)-1,2,3-tri-O-acetyl-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol 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:

acetic acid (64-19-7,77671-22-8) + exo-2, endo-3-diacetoxy-endo-5-acetoxymethyl-7-oxabicyclo[2.2.1]heptane (64589-25-9,90695-20-8,117772-63-1,117772-66-4) → DL-(1,3/2,4,6)-1,2,3-tri-O-acetyl-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol (70838-35-6)

Guidance literature:

With hydrogen bromide;

DOI:10.1246/bcsj.52.1174

Reference yield:

acetic anhydride (108-24-7) + (+/-)-2exo,3exo-diacetoxy-5endo-acxetoxymethyl-7-oxabicyclo<2.2.1>heptane (64589-25-9,90695-20-8,117772-63-1,117772-66-4) → DL-(1,3/2,4,6)-1,2,3-tri-O-acetyl-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol (70838-35-6) + DL-(1,2/3,4,6)-4-acetoxymethyl-1,2-di-O-acetyl-3,6-dibromo-1,2-cyclohexanediol

Guidance literature:

With pyridine; hydrogen bromide; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) acetic acid, 80 deg C, 24 h; 2.) room t.;

DOI:10.1016/0008-6215(88)85054-7

Reference yield: 95.0%

DL-(1,3/2,4,6)-1,2,3-tri-O-acetyl-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol (70838-35-6) → DL-(1,3/2,4,6)-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol (73411-00-4)

Guidance literature:

With hydrogen bromide; In ethanol; Heating;

DOI:10.1246/cl.1980.139

upstream raw materials:

acetic anhydride

(+/-)-2exo,3exo-diacetoxy-5endo-acxetoxymethyl-7-oxabicyclo<2.2.1>heptane

acetic acid

exo-2, endo-3-diacetoxy-endo-5-acetoxymethyl-7-oxabicyclo[2.2.1]heptane

Downstream raw materials:

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

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

C₂₇H₂₈O₁₀

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