Methyl (2S,3S,5R)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoate

Base Information

• Chemical Name: Methyl (2S,3S,5R)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoate
• CAS No.: 152906-21-3
• Molecular Formula: C₃₀H₅₂O₄
• Molecular Weight: 476.74
• Mol file: 152906-21-3.mol

Synonyms:Methyl (2S,3S,5R)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoate

Chemical Property of Methyl (2S,3S,5R)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl (2S,3S,5R)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoate

There total 11 articles about Methyl (2S,3S,5R)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoate 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:

benzyl bromide (100-39-0) → Methyl (2S,3S,5R)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoate (152906-21-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / KH / 1.) THF, 0 deg C, 15 min; room temp., 10 min, 2.) DMF, 0 deg C, 30 min, room temp., 1 h

2: 1.) O₃, 2.) Me₂S, Et₃N / 1.) MeOH, CH₂Cl₂, -78 deg C, 60 min, 2.) room temp., 3 h

3: TiCl₄ / CH₂Cl₂ / 0.75 h / -78 °C

4: 97 percent / CF₃SO₃Ag / CH₂Cl₂ / 2 h / Ambient temperature

5: 1.) LDA / 1.) THF, -50 deg C, 40 min; -30 deg C, 40 min, 2.) HMPA, -50 deg C, 1 h; -20 deg C, 2 h; 0 deg C, 1 h

With dimethylsulfide; silver trifluoromethanesulfonate; potassium hydride; ozone; triethylamine; lithium diisopropyl amide; titanium tetrachloride; In dichloromethane;

DOI:10.1021/jo00079a022

Reference yield:

(R)-3-phenylmethyloxy-tetradecanal (112763-97-0) → Methyl (2S,3S,5R)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoate (152906-21-3)

Guidance literature:

Multi-step reaction with 3 steps

1: TiCl₄ / CH₂Cl₂ / 0.75 h / -78 °C

2: 97 percent / CF₃SO₃Ag / CH₂Cl₂ / 2 h / Ambient temperature

3: 1.) LDA / 1.) THF, -50 deg C, 40 min; -30 deg C, 40 min, 2.) HMPA, -50 deg C, 1 h; -20 deg C, 2 h; 0 deg C, 1 h

With silver trifluoromethanesulfonate; lithium diisopropyl amide; titanium tetrachloride; In dichloromethane;

DOI:10.1021/jo00079a022

Reference yield:

(R)-3-benzyloxy-1-hydroxytetradecane (139623-16-8) → Methyl (2S,3S,5R)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoate (152906-21-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / PDC / CH₂Cl₂ / Ambient temperature

2: TiCl₄ / CH₂Cl₂ / 0.75 h / -78 °C

3: 97 percent / CF₃SO₃Ag / CH₂Cl₂ / 2 h / Ambient temperature

4: 1.) LDA / 1.) THF, -50 deg C, 40 min; -30 deg C, 40 min, 2.) HMPA, -50 deg C, 1 h; -20 deg C, 2 h; 0 deg C, 1 h

With dipyridinium dichromate; silver trifluoromethanesulfonate; lithium diisopropyl amide; titanium tetrachloride; In dichloromethane;

DOI:10.1021/jo00079a022

upstream raw materials:

1-Iodohexane

Methyl (3S,5R)-5-(benzyloxy)-3-hydroxydecanoate

benzyl bromide

(R)-3-phenylmethyloxy-tetradecanal

Downstream raw materials:

(2S,3S,5R)-5-(benzyloxy)-3-hydroxy-2-hexylhexadecanoic acid

Orlistat

(3S,4S)-3-hexyl-4-[(R)-2-hydroxytridecyl]-2-oxetanone

(3S,4S)-4-((R)-2(benzyloxy)tridecyl)-3-hexyl-2-oxetanone