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

Base Information

• Chemical Name: DL-1,2,3-tri-O-acetyl-(1,3/2,4,6)-6-acetoxymethyl-4-bromo-1,2,3-cyclohexanetriol
• CAS No.: 70878-41-0
• Molecular Formula: C₁₅H₂₁BrO₈
• Molecular Weight: 409.231
• Mol file: 70878-41-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about DL-1,2,3-tri-O-acetyl-(1,3/2,4,6)-6-acetoxymethyl-4-bromo-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:

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-(1,3/2,4,6)-6-acetoxymethyl-4-bromo-1,2,3-cyclohexanetriol (70878-41-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / silver fluoride / pyridine / 20 h / 20 °C

2: 1.) NaBH₄, 47percent boron trifluoride etherate, 2.) 3M aq. NaOH, 30percent H₂O₂, 3.) pyridine / 1.) THF, RT, 3.) RT

With pyridine; sodium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; dihydrogen peroxide; silver fluoride; In pyridine;

DOI:10.1246/bcsj.53.455

Reference yield:

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-1,2,3-tri-O-acetyl-(1,3/2,4,6)-6-acetoxymethyl-4-bromo-1,2,3-cyclohexanetriol (70878-41-0)

Guidance literature:

Multi-step reaction with 2 steps

1: HBr

2: (i) MeOCH₂CH₂OH, H₂O, (ii) /BRN= 385737/, Py

With hydrogen bromide;

DOI:10.1246/bcsj.52.1174

Reference yield:

acetic anhydride (108-24-7) + 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) + tetra-O-acetyl-(1,3,6/2,4)-4-bromo-6-hydroxymethyl-1,2,3-cyclohexanetriol

Guidance literature:

With pyridine; sodium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; dihydrogen peroxide; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, RT, 3.) RT;

DOI:10.1246/bcsj.53.455

upstream raw materials:

acetic anhydride

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

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

sodium acetate

Downstream raw materials:

(+/-)-<(1,3/2,4,5)-5-acetamido-2,3,4-triacetoxycyclohexyl>-methyl acetate

(1SR,2RS,3SR,6RS)-1,2,3-triacetoxy-6-(acetoxymethyl)cyclohex-4-ene

DL-1,7:2,3-di-O-isopropylidene-(1,3,4/2,6)-6-hydroxymethyl-4-(p-toluenesulfonamido)-1,2,3-cyclohexanetriol

DL-N-<(3,4,6/5)-3,4,5,6-tetrahydroxy-1-cyclohexenylmethyl>-(1,2,4/3,5)-2,3,4-triacetoxy-5-(acetoxymethyl)cyclohexylamine