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

Base Information

• Chemical Name: benzyl 2-deoxy-2-<(3R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-3-O-tetradecanoyl-β-D-glucopyranoside
• CAS No.: 112166-18-4
• Molecular Formula: C₆₀H₁₀₅NO₉
• Molecular Weight: 984.495
• Mol file: 112166-18-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about benzyl 2-deoxy-2-<(3R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-3-O-tetradecanoyl-β-D-glucopyranoside 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: 97.0%

n-tetradecanoic acid (544-63-8) + benzyl 2-deoxy-2-<(3R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside (102804-08-0) → benzyl 2-deoxy-2-<(3R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-3-O-tetradecanoyl-β-D-glucopyranoside (112166-18-4)

Guidance literature:

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

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

Reference yield:

(3R)-3-hydroxytetradecanoic acid phenacyl ester (87357-65-1) → benzyl 2-deoxy-2-<(3R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-3-O-tetradecanoyl-β-D-glucopyranoside (112166-18-4)

Guidance literature:

Multi-step reaction with 4 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 percent / 3-(3-dimethylamino)propyl-1-ethylcarbodiimide hydrochloride, 4-(dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

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

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

Reference yield:

(R)-3-(hexadecanoyl)oxy-tetradecanoic acid (93390-37-5) → benzyl 2-deoxy-2-<(3R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-3-O-tetradecanoyl-β-D-glucopyranoside (112166-18-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 97 percent / 3-(3-dimethylamino)propyl-1-ethylcarbodiimide hydrochloride, 4-(dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

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

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

upstream raw materials:

n-tetradecanoic acid

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

(3R)-3-hydroxytetradecanoic acid phenacyl ester

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

Downstream raw materials:

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

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