Hexaacyl monophosphoryl lipid A

Base Information

• Chemical Name: Hexaacyl monophosphoryl lipid A
• CAS No.: 88598-53-2
• Deprecated CAS: 126924-61-6,103426-88-6,114420-33-6
• Molecular Formula: C94H177N2O22P
• Molecular Weight: 1718.385141
• UNII: Q2VF73396U
• Wikidata: Q27284267

Synonyms:Compound 504;TLC 3;LA 15PH;Hexaacyl monophosphoryl lipid A;Q2VF73396U;88598-53-2;GLA (ADJUVANT);UNII-MWC0ET1L2P;TLC-3;LA-15PH;LIPID A 504;UNII-Q2VF73396U;C94H177N2O22P;alpha-D-glucopyranose, 2-deoxy-6-O-(2-deoxy-2-(((3R)-1-oxo-3-((1-oxododecyl)oxy)tetradecyl)amido)-3-O-((3R)-1-oxo-3-((1-oxotetradecyl)oxy)tetradecyl)-4-O-phosphono-beta-D-glucopyranosyl)-2-(((3R)-3-hydroxy-1-oxotetradecyl)amino)-, 3-((3R)-3-hydroxytetradecanoate);GLUCOPYRANOSYL LIPID ADJUVANT;C94-H177-N2-O22-P;MONOPHOSPHORYL LIPID A (SYNTHETIC) FREE ACID;Q27284267;.ALPHA.-D-GLUCOPYRANOSE, 2-DEOXY-6-O-(2-DEOXY-2-(((3R)-1-OXO-3-((1-OXODODECYL)OXY)TETRADECYL)AMINO)-3-O-((3R)-1-OXO-3-((1-OXOTETRADECYL)OXY)TETRADECYL)-4-O-PHOSPHONO-.BETA.-D-GLUCOPYRANOSYL)-2-(((3R)-3-HYDROXY-1-OXOTETRADECYL)AMINO)-, 3-((3R)-3-HYDROXYTETRADECANOATE)

Chemical Property of Hexaacyl monophosphoryl lipid A

Chemical Property:

• XLogP3: 27.5
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 22
• Rotatable Bond Count: 86
• Exact Mass: 1718.25641711
• Heavy Atom Count: 119
• Complexity: 2520

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(C(OC(C1OP(=O)(O)O)CO)OCC2C(C(C(C(O2)O)NC(=O)CC(CCCCCCCCCCC)O)OC(=O)CC(CCCCCCCCCCC)O)O)NC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC
• Isomeric SMILES: CCCCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCC)CC(=O)O[C@@H]1[C@H]([C@@H](O[C@@H]([C@H]1OP(=O)(O)O)CO)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)O)NC(=O)C[C@@H](CCCCCCCCCCC)O)OC(=O)C[C@@H](CCCCCCCCCCC)O)O)NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC

Technology Process of Hexaacyl monophosphoryl lipid A

There total 4 articles about Hexaacyl monophosphoryl lipid A 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: 91.5%

C138H209N2O22P → 2-deoxy-6-O-<2-deoxy-2-<(R)-3-dodecanoyloxytetradecanoylamino>-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranosyl>-3-O-<(R)-3-hydroxytetradecanoyl>-2-<(R)-3-hydroxytetradecanoylamino>-D-glucose 4'-phosphate (88598-53-2,114420-33-6,103426-88-6)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In chloroform; at 30 ℃; for 1.33333h; Inert atmosphere;

Reference yield: 81.0%

C144H220N2O25P2 (230966-96-8) → 2-deoxy-6-O-<2-deoxy-2-<(R)-3-dodecanoyloxytetradecanoylamino>-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranosyl>-3-O-<(R)-3-hydroxytetradecanoyl>-2-<(R)-3-hydroxytetradecanoylamino>-α-D-glucopyranose 1,4'-bis(phosphate) (95991-05-2,105307-37-7,130792-91-5) + 2-deoxy-6-O-<2-deoxy-2-<(R)-3-dodecanoyloxytetradecanoylamino>-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranosyl>-3-O-<(R)-3-hydroxytetradecanoyl>-2-<(R)-3-hydroxytetradecanoylamino>-D-glucose 4'-phosphate (88598-53-2,114420-33-6,103426-88-6)

Guidance literature:

With hydrogen; palladium; In tetrahydrofuran; at 20 ℃; under 5148.56 Torr;

DOI:10.1246/bcsj.72.1377

Reference yield:

C106H185N2O22P → 2-deoxy-6-O-<2-deoxy-2-<(R)-3-dodecanoyloxytetradecanoylamino>-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranosyl>-3-O-<(R)-3-hydroxytetradecanoyl>-2-<(R)-3-hydroxytetradecanoylamino>-D-glucose 4'-phosphate (88598-53-2,114420-33-6,103426-88-6)

Guidance literature:

With hydrogen; platinum(IV) oxide; Yield given;

DOI:10.1016/S0040-4039(00)61962-7

upstream raw materials:

benzyl 3-O-<(R)-3-benzyloxytetradecanoyl>-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-6-O-<2-deoxy-2-<(R)-3-dodecanoyloxytetradecanoylamino>-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranosyl>-α-D-glucopyranoside 4'-(diphenyl phosphate)

C₁₄₄H₂₂₀N₂O₂₅P₂

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