(R)-3-Benzyloxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-allyloxy-5-benzyloxy-6-benzyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: (R)-3-Benzyloxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-allyloxy-5-benzyloxy-6-benzyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester
• CAS No.: 93390-33-1
• Molecular Formula: C₆₅H₉₃NO₉
• Molecular Weight: 1032.45
• Mol file: 93390-33-1.mol

Synonyms:

Chemical Property of (R)-3-Benzyloxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-allyloxy-5-benzyloxy-6-benzyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-Benzyloxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-allyloxy-5-benzyloxy-6-benzyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester

There total 2 articles about (R)-3-Benzyloxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-allyloxy-5-benzyloxy-6-benzyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-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: 56.0%

(R)-3-benzyloxytetradecanoic acid (87357-67-3) + (2R,3R,4R,5S,6R)-2-Allyloxy-3-amino-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ol (93390-32-0) → (R)-3-Benzyloxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-allyloxy-5-benzyloxy-6-benzyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester (93390-33-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/0040-4039(84)80116-1

Reference yield:

Benzoic acid (2R,3R,4R,5S,6R)-2-allyloxy-3-amino-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl ester → (R)-3-Benzyloxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-allyloxy-5-benzyloxy-6-benzyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester (93390-33-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.1N NaOMe / methanol / 15 h / Ambient temperature

2: 56 percent / DCC, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; sodium methylate; dicyclohexyl-carbodiimide; In methanol; dichloromethane;

DOI:10.1016/0040-4039(84)80116-1

Reference yield:

(R)-3-Benzyloxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-allyloxy-5-benzyloxy-6-benzyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester (93390-33-1) → (R)-3-Benzyloxy-tetradecanoic acid (2R,3S,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-5-((R)-3-benzyloxy-tetradecanoylamino)-6-[((E)-propenyl)oxy]-tetrahydro-pyran-4-yl ester

Guidance literature:

With (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; In tetrahydrofuran; at 50 ℃; for 1h;

DOI:10.1016/0040-4039(84)80116-1

upstream raw materials:

(R)-3-benzyloxytetradecanoic acid

(2R,3R,4R,5S,6R)-2-Allyloxy-3-amino-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ol

Downstream raw materials:

Lipid X

lipid Y

(R)-3-Benzyloxy-tetradecanoic acid (2R,3S,4R,5R,6S)-3-benzyloxy-2-benzyloxymethyl-5-((R)-3-benzyloxy-tetradecanoylamino)-6-hydroxy-tetrahydro-pyran-4-yl ester

(R)-3-Benzyloxy-tetradecanoic acid (2R,3S,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-5-((R)-3-benzyloxy-tetradecanoylamino)-6-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-4-yl ester