Hexadecanoic acid (R)-1-{[(2R,3R,4R,5S,6R)-2-benzyloxy-4-((R)-3-benzyloxymethoxy-tetradecanoyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-ylcarbamoyl]-methyl}-dodecyl ester

Base Information

• Chemical Name: Hexadecanoic acid (R)-1-{[(2R,3R,4R,5S,6R)-2-benzyloxy-4-((R)-3-benzyloxymethoxy-tetradecanoyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-ylcarbamoyl]-methyl}-dodecyl ester
• CAS No.: 112166-28-6
• Molecular Formula: C₆₅H₁₀₉NO₁₁
• Molecular Weight: 1080.58
• Mol file: 112166-28-6.mol

Synonyms:

Chemical Property of Hexadecanoic acid (R)-1-{[(2R,3R,4R,5S,6R)-2-benzyloxy-4-((R)-3-benzyloxymethoxy-tetradecanoyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-ylcarbamoyl]-methyl}-dodecyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Hexadecanoic acid (R)-1-{[(2R,3R,4R,5S,6R)-2-benzyloxy-4-((R)-3-benzyloxymethoxy-tetradecanoyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-ylcarbamoyl]-methyl}-dodecyl ester

There total 8 articles about Hexadecanoic acid (R)-1-{[(2R,3R,4R,5S,6R)-2-benzyloxy-4-((R)-3-benzyloxymethoxy-tetradecanoyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-ylcarbamoyl]-methyl}-dodecyl ester 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: 91.3%

benzyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-2-<(3R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside (112166-20-8) → Hexadecanoic acid (R)-1-{[(2R,3R,4R,5S,6R)-2-benzyloxy-4-((R)-3-benzyloxymethoxy-tetradecanoyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-ylcarbamoyl]-methyl}-dodecyl ester (112166-28-6)

Guidance literature:

With acetic acid;

DOI:10.1016/0008-6215(87)80220-3

Reference yield:

(3R)-3-(Benzyloxymethoxy)tetradecanoic acid (111247-11-1) → Hexadecanoic acid (R)-1-{[(2R,3R,4R,5S,6R)-2-benzyloxy-4-((R)-3-benzyloxymethoxy-tetradecanoyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-ylcarbamoyl]-methyl}-dodecyl ester (112166-28-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 97.7 percent / 3-(3-dimethylamino)propyl-1-ethylcarbodiimide hydrochloride, 4-(dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

2: 91.3 percent / 95percent acetic acid

With dmap; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

DOI:10.1016/0008-6215(87)80220-3

Reference yield:

(3R)-3-hydroxytetradecanoic acid phenacyl ester (87357-65-1) → Hexadecanoic acid (R)-1-{[(2R,3R,4R,5S,6R)-2-benzyloxy-4-((R)-3-benzyloxymethoxy-tetradecanoyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-ylcarbamoyl]-methyl}-dodecyl ester (112166-28-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 99.4 percent / DMAP / CH₂Cl₂; pyridine / Ambient temperature

2: zinc dust, acetic acid / 50 °C

3: 93.5 percent / 3-(3-dimethylamino)propyl-1-ethylcarbodiimide hydrochloride / CH₂Cl₂ / Ambient temperature

4: 97.7 percent / 3-(3-dimethylamino)propyl-1-ethylcarbodiimide hydrochloride, 4-(dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

5: 91.3 percent / 95percent acetic acid

With dmap; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; In pyridine; dichloromethane;

DOI:10.1016/0008-6215(87)80220-3

upstream raw materials:

benzyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-2-<(3R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside

(3R)-3-(Benzyloxymethoxy)tetradecanoic acid

(3R)-3-hydroxytetradecanoic acid phenacyl ester

(R)-3-(hexadecanoyl)oxy-tetradecanoic acid