(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

Base Information

• Chemical Name: (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
• CAS No.: 93390-42-2
• Molecular Formula: C₇₆H₁₀₂NO₁₂P
• Molecular Weight: 1252.62
• Mol file: 93390-42-2.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 5 articles about (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 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:

(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,3S,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-5-((R)-3-benzyloxy-tetradecanoylamino)-6-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-4-yl ester (93390-42-2)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 2)2>PF₆ / tetrahydrofuran / 1 h / 50 °C

3: 63 percent / I₂ / tetrahydrofuran; H₂O

4: 1.) butyllithium / 1.) THF, -78 deg C 2.) -78 deg C

With dmap; n-butyllithium; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; iodine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water;

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,3S,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-5-((R)-3-benzyloxy-tetradecanoylamino)-6-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-4-yl ester (93390-42-2)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: 2)2>PF₆ / tetrahydrofuran / 1 h / 50 °C

4: 63 percent / I₂ / tetrahydrofuran; H₂O

5: 1.) butyllithium / 1.) THF, -78 deg C 2.) -78 deg C

With dmap; n-butyllithium; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; iodine; sodium methylate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; water;

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-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-4-yl ester (93390-42-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 2)2>PF₆ / tetrahydrofuran / 1 h / 50 °C

2: 63 percent / I₂ / tetrahydrofuran; H₂O

3: 1.) butyllithium / 1.) THF, -78 deg C 2.) -78 deg C

With n-butyllithium; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; iodine; In tetrahydrofuran; water;

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

upstream raw materials:

dibenzyl phosphochloridate

(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

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

(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

Downstream raw materials:

(R)-3-Hydroxy-tetradecanoic acid (3R,4R,5S,6R)-2,5-dihydroxy-6-hydroxymethyl-3-((R)-3-hydroxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester

Lipid X