(5S,6R)-6-(benzyloxy)-5-hexadecanolide

Base Information

• Chemical Name: (5S,6R)-6-(benzyloxy)-5-hexadecanolide
• CAS No.: 88948-60-1
• Molecular Formula: C₂₃H₃₆O₃
• Molecular Weight: 360.537
• Mol file: 88948-60-1.mol

Synonyms:

Chemical Property of (5S,6R)-6-(benzyloxy)-5-hexadecanolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6R)-6-(benzyloxy)-5-hexadecanolide

There total 11 articles about (5S,6R)-6-(benzyloxy)-5-hexadecanolide 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:

(5S,6R)-6-Benzyloxy-5-hydroxy-hexadecanoic acid → (5S,6R)-6-(benzyloxy)-5-hexadecanolide (88948-60-1)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 1h; Ambient temperature;

DOI:10.1021/jo00376a056

Reference yield:

benzyl bromide (100-39-0) → (5S,6R)-6-(benzyloxy)-5-hexadecanolide (88948-60-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / sodium hydride / tetrahydrofuran / 10 h / Heating

2: 82 percent / N-chlorossucinimide, sodium bicarbonate, silver nitrate / acetone; H₂O / 0.17 h / Ambient temperature

3: diethyl ether / 1 h / -78 °C

4: 93 percent / 4-dimethylaminopyridine / Ambient temperature

5: 1.) ozone, 2.) dimethyl sulfide / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 1 h

6: 2-methyl-2-butene, sodium chlorite, KH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 0.5 h / Ambient temperature

7: NaOH / methanol; H₂O / 1 h / Heating

8: p-TsOH / benzene / 1 h / Ambient temperature

With dmap; sodium hydroxide; sodium chlorite; potassium dihydrogenphosphate; N-chloro-succinimide; 2-methyl-but-2-ene; dimethylsulfide; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; silver nitrate; In tetrahydrofuran; methanol; diethyl ether; water; acetone; tert-butyl alcohol; benzene;

DOI:10.1021/jo00376a056

Reference yield:

(R)-2-(benzyloxy)dodecanal (85514-80-3) → (5S,6R)-6-(benzyloxy)-5-hexadecanolide (88948-60-1)

Guidance literature:

Multi-step reaction with 6 steps

1: diethyl ether / 1 h / -78 °C

2: 93 percent / 4-dimethylaminopyridine / Ambient temperature

3: 1.) ozone, 2.) dimethyl sulfide / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 1 h

4: 2-methyl-2-butene, sodium chlorite, KH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 0.5 h / Ambient temperature

5: NaOH / methanol; H₂O / 1 h / Heating

6: p-TsOH / benzene / 1 h / Ambient temperature

With dmap; sodium hydroxide; sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene; dimethylsulfide; toluene-4-sulfonic acid; ozone; In methanol; diethyl ether; water; tert-butyl alcohol; benzene;

DOI:10.1021/jo00376a056

upstream raw materials:

benzyl bromide

(R)-2-(benzyloxy)dodecanal

(6S,7R)-7-(benzyloxy)-heptadec-1-en-6-ol

(6S,7R)-6-acetoxy-7-(benzyloxy)-1-heptadecene

Downstream raw materials:

(5S,6R)-6-hydroxy-5-hexadecanolide