benzyl (2S,3S,5R)-3-(benzyloxy)-2-hexyl-5-<(tetrahydro-2H-pyran-2-yl)oxy>hexadecanoate

Base Information

• Chemical Name: benzyl (2S,3S,5R)-3-(benzyloxy)-2-hexyl-5-<(tetrahydro-2H-pyran-2-yl)oxy>hexadecanoate
• CAS No.: 112764-04-2
• Molecular Formula: C₄₁H₆₄O₅
• Molecular Weight: 636.956
• Mol file: 112764-04-2.mol

Synonyms:benzyl (2S,3S,5R)-3-(benzyloxy)-2-hexyl-5-<(tetrahydro-2H-pyran-2-yl)oxy>hexadecanoate

Chemical Property of benzyl (2S,3S,5R)-3-(benzyloxy)-2-hexyl-5-<(tetrahydro-2H-pyran-2-yl)oxy>hexadecanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S,3S,5R)-3-(benzyloxy)-2-hexyl-5-<(tetrahydro-2H-pyran-2-yl)oxy>hexadecanoate

There total 9 articles about benzyl (2S,3S,5R)-3-(benzyloxy)-2-hexyl-5-<(tetrahydro-2H-pyran-2-yl)oxy>hexadecanoate 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: 73.0%

3,4-dihydro-2H-pyran (110-87-2) + benzyl (2S,3S,5R)-3-(benzyloxy)-2-hexyl-5-hydroxyhexadecanoate (112764-03-1) → benzyl (2S,3S,5R)-3-(benzyloxy)-2-hexyl-5-<(tetrahydro-2H-pyran-2-yl)oxy>hexadecanoate (112764-04-2)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at -10 - 20 ℃; for 3h;

DOI:10.1021/jo00241a018

Reference yield:

Octanoic acid (124-07-2) → benzyl (2S,3S,5R)-3-(benzyloxy)-2-hexyl-5-<(tetrahydro-2H-pyran-2-yl)oxy>hexadecanoate (112764-04-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) diisopropylamine, BuLi / 1.) THF, hexane, a) -50 deg C, 15 min, b) RT, 1 h, 2.) -78 deg C, 3 h

2: H₂ / 10percent Pd/C / tetrahydrofuran / 760 Torr / Ambient temperature

3: p-TsOH, / CHCl₃ / Ambient temperature

4: Jones' reagent / acetone / 1 h / 10 °C

5: 84 percent / H₂ / PtO₂ / ethyl acetate / 48 h / 37503 Torr / Ambient temperature

6: 73 percent / CF₃SO₃H / CH₂Cl₂ / 2 h / 0 - 20 °C

7: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h

8: 73 percent / p-toluenesulfonic acid / CH₂Cl₂ / 3 h / -10 - 20 °C

With potassium hydroxide; n-butyllithium; jones' reagent; trifluorormethanesulfonic acid; hydrogen; toluene-4-sulfonic acid; diisopropylamine; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; acetone;

DOI:10.1021/jo00241a018

Reference yield:

(R)-3-phenylmethyloxy-tetradecanal (112763-97-0) → benzyl (2S,3S,5R)-3-(benzyloxy)-2-hexyl-5-<(tetrahydro-2H-pyran-2-yl)oxy>hexadecanoate (112764-04-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) diisopropylamine, BuLi / 1.) THF, hexane, a) -50 deg C, 15 min, b) RT, 1 h, 2.) -78 deg C, 3 h

2: H₂ / 10percent Pd/C / tetrahydrofuran / 760 Torr / Ambient temperature

3: p-TsOH, / CHCl₃ / Ambient temperature

4: Jones' reagent / acetone / 1 h / 10 °C

5: 84 percent / H₂ / PtO₂ / ethyl acetate / 48 h / 37503 Torr / Ambient temperature

6: 73 percent / CF₃SO₃H / CH₂Cl₂ / 2 h / 0 - 20 °C

7: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h

8: 73 percent / p-toluenesulfonic acid / CH₂Cl₂ / 3 h / -10 - 20 °C

With potassium hydroxide; n-butyllithium; jones' reagent; trifluorormethanesulfonic acid; hydrogen; toluene-4-sulfonic acid; diisopropylamine; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; acetone;

DOI:10.1021/jo00241a018

upstream raw materials:

3,4-dihydro-2H-pyran

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

Octanoic acid

(3S,4S,6R)-3-Hexyl-3,4,5,6-tetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one

Downstream raw materials:

(S)-N-(benzyloxycarbonyl)asparagine (S)-1-<<(2S,3S)-3-hexyl-4-oxo-2-oxetanyl>methyl>dodecyl ester

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

(3S,4S,6R)-4-(benzyloxy)-3-hexyl-3,4,5,6-tetrahydro-6-undecyl-2H-pyran-2-one

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

Refernces