4,8-anhydro-2,3,5-trideoxy-7-O-diphenylphosphono-5-[(R)-3-(hydroxy)tetradecanoylamino]-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid

Base Information

• Chemical Name: 4,8-anhydro-2,3,5-trideoxy-7-O-diphenylphosphono-5-[(R)-3-(hydroxy)tetradecanoylamino]-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid
• CAS No.: 352522-50-0
• Molecular Formula: C₆₃H₁₀₄NO₁₄P
• Molecular Weight: 1130.49

Synonyms:4,8-anhydro-2,3,5-trideoxy-7-O-diphenylphosphono-5-[(R)-3-(hydroxy)tetradecanoylamino]-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid

Chemical Property of 4,8-anhydro-2,3,5-trideoxy-7-O-diphenylphosphono-5-[(R)-3-(hydroxy)tetradecanoylamino]-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 4,8-anhydro-2,3,5-trideoxy-7-O-diphenylphosphono-5-[(R)-3-(hydroxy)tetradecanoylamino]-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid

There total 11 articles about 4,8-anhydro-2,3,5-trideoxy-7-O-diphenylphosphono-5-[(R)-3-(hydroxy)tetradecanoylamino]-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid 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:

4,8-anhydro-9-O-benzyloxycarbonyl-5-[(R)-3-(benzyloxytetradecanoyl)amino]-2,3,5-trideoxy-7-O-diphenylphosphono-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid → 4,8-anhydro-2,3,5-trideoxy-7-O-diphenylphosphono-5-[(R)-3-(hydroxy)tetradecanoylamino]-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid (352522-50-0)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; at 20 ℃;

DOI:10.1016/S0008-6215(01)00290-7

Reference yield:

3,4,6-tri-O-acetyl-2-(benzoyloxycarbonyl)amino-2-deoxy-α-D-glucopyranosyl bromide (73446-41-0) → 4,8-anhydro-2,3,5-trideoxy-7-O-diphenylphosphono-5-[(R)-3-(hydroxy)tetradecanoylamino]-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid (352522-50-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 60 percent / 2,2'-azobis-(2,4-dimethyl-4-methoxyvaleronitrile); Bu₃SnH / diethyl ether / 1 h / 20 °C

2: H₂ / Pd(OH)2/C / ethanol / 0.33 h / 20 °C

3: 626 mg / 3-(3-dimrthylaminopropyl)-1-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 20 °C

4: NaOMe / methanol / 0.33 h / 20 °C

5: 485 mg / TsOH*H₂O / dimethylformamide / 1 h / 20 °C

6: 88 percent / DMAP; DCC / CH₂Cl₂ / 7 h / 20 °C

7: 95 percent / TsOH*H₂O / methanol / 2 h / 20 °C

8: 93 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C

9: 94 percent / DMAP / CH₂Cl₂ / 4 h / 20 °C

10: TFA / CH₂Cl₂ / 4 h / 20 °C

11: 42.1 mg / H₂ / Pd(OH)2/C / ethanol / 20 °C

With pyridine; dmap; 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile; hydrogen; tri-n-butyl-tin hydride; sodium methylate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dihydroxide; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(01)00290-7

Reference yield:

6,7,9-tri-O-acetyl-5-amino-4,8-anhydro-2,3,5-trideoxy-D-glycero-D-ido-nononic acid tert-butyl ester → 4,8-anhydro-2,3,5-trideoxy-7-O-diphenylphosphono-5-[(R)-3-(hydroxy)tetradecanoylamino]-6-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-nononic acid (352522-50-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 626 mg / 3-(3-dimrthylaminopropyl)-1-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 20 °C

2: NaOMe / methanol / 0.33 h / 20 °C

3: 485 mg / TsOH*H₂O / dimethylformamide / 1 h / 20 °C

4: 88 percent / DMAP; DCC / CH₂Cl₂ / 7 h / 20 °C

5: 95 percent / TsOH*H₂O / methanol / 2 h / 20 °C

6: 93 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C

7: 94 percent / DMAP / CH₂Cl₂ / 4 h / 20 °C

8: TFA / CH₂Cl₂ / 4 h / 20 °C

9: 42.1 mg / H₂ / Pd(OH)2/C / ethanol / 20 °C

With pyridine; dmap; hydrogen; sodium methylate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dihydroxide; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(01)00290-7

upstream raw materials:

3,4,6-tri-O-acetyl-2-(benzoyloxycarbonyl)amino-2-deoxy-α-D-glucopyranosyl bromide

6,7,9-tri-O-acetyl-4,8-anhydro-2,3,5-trideoxy-5-benzyloxycarbonylamino-D-glycero-D-ido-nononic acid tert-butyl ester

4,8-anhydro-5-[(R)-3-(benzyloxytetradecanoyl)amino]-2,3,5-trideoxy-7,9-O-isopropylidene-D-glycero-D-ido-nononic acid tert-butyl ester

6,7,9-tri-O-acetyl-4,8-anhydro-5-[(R)-3-(benzyloxytetradecanoyl)amino]-2,3,5-trideoxy-D-glycero-D-ido-nononic acid tert-butyl ester

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