2-Tetradecyl-hexadecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-3-(3-hydroxy-dodecanoylamino)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: 2-Tetradecyl-hexadecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-3-(3-hydroxy-dodecanoylamino)-tetrahydro-pyran-4-yl ester
• CAS No.: 124710-51-6
• Molecular Formula: C₇₅H₁₁₆NO₁₂P
• Molecular Weight: 1254.72
• Mol file: 124710-51-6.mol

Synonyms:

Chemical Property of 2-Tetradecyl-hexadecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-3-(3-hydroxy-dodecanoylamino)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Tetradecyl-hexadecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-3-(3-hydroxy-dodecanoylamino)-tetrahydro-pyran-4-yl ester

There total 9 articles about 2-Tetradecyl-hexadecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-3-(3-hydroxy-dodecanoylamino)-tetrahydro-pyran-4-yl 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: 80.0%

3-hydroxydodecanoic acid (1883-13-2,53941-38-1) + Benzyl 2-amino-6-O-benzyloxymethyl-2-deoxy-4-O-(diphenoxyphosphinyl)-3-O-(2-tetradecylhexadecanoyl)-β-D-glucopyranoside (124710-44-7) → 2-Tetradecyl-hexadecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-3-(3-hydroxy-dodecanoylamino)-tetrahydro-pyran-4-yl ester (124710-51-6,124710-70-9)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; Ambient temperature;

DOI:10.1016/0008-6215(91)80013-D

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → 2-Tetradecyl-hexadecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-3-(3-hydroxy-dodecanoylamino)-tetrahydro-pyran-4-yl ester (124710-51-6,124710-70-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 52 percent / 1,1,3,3-tetramethylurea / CH₂Cl₂ / Ambient temperature

2: 4-dimethylaminopyridine, pyridine / CH₂Cl₂ / Ambient temperature

3: 1.8 g / zinc dust, acetic acid / 3 h / 60 °C

4: 80 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / Ambient temperature

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

DOI:10.1016/0008-6215(91)80013-D

Reference yield:

2-tetradecylhexadecanoic acid (66880-77-1) → 2-Tetradecyl-hexadecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-3-(3-hydroxy-dodecanoylamino)-tetrahydro-pyran-4-yl ester (124710-51-6,124710-70-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 4-dimethylaminopyridine / 1,2-dichloro-ethane / Ambient temperature

2: 3.5 g / 80percent aq. acetic acid / 3 h / 50 °C

3: 52 percent / 1,1,3,3-tetramethylurea / CH₂Cl₂ / Ambient temperature

4: 4-dimethylaminopyridine, pyridine / CH₂Cl₂ / Ambient temperature

5: 1.8 g / zinc dust, acetic acid / 3 h / 60 °C

6: 80 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / Ambient temperature

With pyridine; dmap; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tetramethylurea; zinc; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(91)80013-D

upstream raw materials:

3-hydroxydodecanoic acid

Benzyl 2-amino-6-O-benzyloxymethyl-2-deoxy-4-O-(diphenoxyphosphinyl)-3-O-(2-tetradecylhexadecanoyl)-β-D-glucopyranoside

Benzyloxymethyl chloride

2-tetradecylhexadecanoic acid

Refernces