(2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol

Base Information

• Chemical Name: (2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol
• CAS No.: 914803-37-5
• Molecular Formula: C₅₃H₈₇NO₁₁
• Molecular Weight: 914.274
• Mol file: 914803-37-5.mol

Synonyms:(2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol

Chemical Property of (2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol

There total 18 articles about (2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol 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:

(2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'->1)-2-amino-3-O-benzoyl-4-octadecene-1,3-diol + 1-hexadecylcarboxylic acid (57-10-3) → (2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol (914803-37-5)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20 ℃; for 10h;

DOI:10.1080/07328300600859825

Reference yield:

(2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'->1)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol (914803-33-1) → (2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol (914803-37-5)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine / tetrahydrofuran; H₂O / 45 °C

2: 168 mg / triethylamine; 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 10 h / 20 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1080/07328300600859825

Reference yield:

(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol (103348-50-1) → (2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol (914803-37-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 98.2 percent / BF₃*OEt₂; molecular sieves 4 Angstroem / CH₂Cl₂ / -20 °C

2: triphenylphosphine / tetrahydrofuran; H₂O / 45 °C

3: 168 mg / triethylamine; 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 10 h / 20 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1080/07328300600859825

upstream raw materials:

1-hexadecylcarboxylic acid

(2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'->1)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol

(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate