(1S,5R)-5-methyl-1-para-toluenesulfonyloxymethyl-6,8-dioxabicyclo[3.2.1]octane

Base Information

• Chemical Name: (1S,5R)-5-methyl-1-para-toluenesulfonyloxymethyl-6,8-dioxabicyclo[3.2.1]octane
• CAS No.: 111650-02-3
• Molecular Formula: C₁₅H₂₀O₅S
• Molecular Weight: 312.387
• Mol file: 111650-02-3.mol

Synonyms:(1S,5R)-5-methyl-1-para-toluenesulfonyloxymethyl-6,8-dioxabicyclo[3.2.1]octane

Chemical Property of (1S,5R)-5-methyl-1-para-toluenesulfonyloxymethyl-6,8-dioxabicyclo[3.2.1]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5R)-5-methyl-1-para-toluenesulfonyloxymethyl-6,8-dioxabicyclo[3.2.1]octane

There total 25 articles about (1S,5R)-5-methyl-1-para-toluenesulfonyloxymethyl-6,8-dioxabicyclo[3.2.1]octane 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: 95.0%

Toluene-4-sulfonic acid (S)-2-benzyloxy-2-hydroxymethyl-6-oxo-heptyl ester (204325-80-4) → (1S,5R)-5-methyl-1-para-toluenesulfonyloxymethyl-6,8-dioxabicyclo[3.2.1]octane (111650-02-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 72h; under 760 Torr;

DOI:10.1248/cpb.46.217

Reference yield: 95.0%

(6S)-6,7-O-isopropylidene-6,7-dihydroxy-6-p-toluenesulfonyloxymethyl-hepta-2-one (120633-58-1) → (1S,5R)-5-methyl-1-para-toluenesulfonyloxymethyl-6,8-dioxabicyclo[3.2.1]octane (111650-02-3)

Guidance literature:

With Amberlysr-15 resin; In chloroform; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)90101-2

Reference yield:

(-)-(2R)-2-hydroxy-2-(hydroxymethyl)-2,2'-O-isopropylidenepent-4-enol (212763-45-6) → (1S,5R)-5-methyl-1-para-toluenesulfonyloxymethyl-6,8-dioxabicyclo[3.2.1]octane (111650-02-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / pyridine / Ambient temperature

2: 1.) O₃, 2.) PPh₃ / 1.) MeOH, -78 deg C, 3 h; 2.) CH₂Cl₂,48 h

3: 68 percent / acetonitrile / 2 h / Heating

4: hydrogen / 10percent Pd/C / ethanol

With pyridine; hydrogen; ozone; triphenylphosphine; palladium on activated charcoal; In ethanol; acetonitrile;

DOI:10.1016/S0040-4020(01)90101-2

upstream raw materials:

(6S)-6,7-O-isopropylidene-6,7-dihydroxy-6-p-toluenesulfonyloxymethyl-hept-3-ene-(E)-2-one

(6S)-6,7-O-isopropylidene-6,7-dihydroxy-6-p-toluenesulfonyloxymethyl-hepta-2-one

Toluene-4-sulfonic acid (S)-2-benzyloxy-2-hydroxymethyl-6-oxo-heptyl ester

ethylene-cetal de la bromo-5 pentanone-2