D,L-(1,3,5/2,4)-1-C-acetoxy-methyl-1,2,3,4-tetra-O-acetyl-5-bromo-1,2,3,4-cyclohexanetetrol

Base Information

• Chemical Name: D,L-(1,3,5/2,4)-1-C-acetoxy-methyl-1,2,3,4-tetra-O-acetyl-5-bromo-1,2,3,4-cyclohexanetetrol
• CAS No.: 104748-81-4
• Molecular Formula: C₁₇H₂₃BrO₁₀
• Molecular Weight: 467.268
• Mol file: 104748-81-4.mol

Synonyms:D,L-(1,3,5/2,4)-1-C-acetoxy-methyl-1,2,3,4-tetra-O-acetyl-5-bromo-1,2,3,4-cyclohexanetetrol

Chemical Property of D,L-(1,3,5/2,4)-1-C-acetoxy-methyl-1,2,3,4-tetra-O-acetyl-5-bromo-1,2,3,4-cyclohexanetetrol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of D,L-(1,3,5/2,4)-1-C-acetoxy-methyl-1,2,3,4-tetra-O-acetyl-5-bromo-1,2,3,4-cyclohexanetetrol

There total 3 articles about D,L-(1,3,5/2,4)-1-C-acetoxy-methyl-1,2,3,4-tetra-O-acetyl-5-bromo-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: 72.0%

acetic anhydride (108-24-7) + D,L-(1,3,5/2,4)-1-C-acetoxymethyl-2,3,4-tri-O-acetyl-5-bromo-1,2,3,4-cyclohexanetetrol (102562-09-4,104832-56-6,148347-72-2) → D,L-(1,3,5/2,4)-1-C-acetoxy-methyl-1,2,3,4-tetra-O-acetyl-5-bromo-1,2,3,4-cyclohexanetetrol (104748-81-4)

Guidance literature:

With pyridine; dmap; at 70 ℃; for 1h;

DOI:10.1016/S0008-6215(00)90393-8

Reference yield: 7.0%

→ D,L-(1,3,5/2,4)-1-C-acetoxymethyl-2,3,4,5-tetra-O-acetyl-1,2,3,4,5-cyclohexanepentol (103781-86-8,109958-59-0,109958-60-3,109958-62-5,109958-64-7) + D,L-(1,3,5/2,4)-1-C-acetoxy-methyl-1,2,3,4-tetra-O-acetyl-5-bromo-1,2,3,4-cyclohexanetetrol (104748-81-4)

Guidance literature:

With sodium acetate; In 2-methoxy-ethanol; water; for 17h; Heating;

DOI:10.1016/S0008-6215(00)90122-8

Reference yield:

DL-1,2,3-tri-O-acetyl-(1,3/2,4)-4-bromo-6-methylene-1,2,3-cyclohexenetriol (74023-99-7) → D,L-(1,3,5/2,4)-1-C-acetoxy-methyl-1,2,3,4-tetra-O-acetyl-5-bromo-1,2,3,4-cyclohexanetetrol (104748-81-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 35percent hydrogen peroxide, 2.) pyridine, osmium tetroxide / 1.) t-butanol, H₂O, RT, 18 h, 2.) RT

2: 72 percent / pyridine, 4-dimethylamino-pyridine / 1 h / 70 °C

With pyridine; dmap; osmium(VIII) oxide; dihydrogen peroxide;

DOI:10.1016/S0008-6215(00)90393-8

upstream raw materials:

acetic anhydride

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

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

Downstream raw materials:

(1RS,2SR,3RS,4SR,5RS)-1,2,3,4-tetra-acetoxy-6-oxabicyclo<3.2.1>octane

D,L-(1,3,5/2,4)-1-C-acetoxymethyl-2,3,4,5-tetra-O-acetyl-1,2,3,4,5-cyclohexanepentol

Acetic acid (1S,2R,3S,4R,5R)-2,3,4,5-tetraacetoxy-1-acetoxymethyl-cyclohexyl ester

D,L-(1,3/2,4)-1-C-acetoxymethyl-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol