Benzoic acid (E)-(R)-1-[(S)-2-((2S,3aR,5R,6S,7S,7aR)-6,7-diacetoxy-5-acetoxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-2-yloxy)-1-hexadecanoylamino-ethyl]-hexadec-2-enyl ester

Base Information

• Chemical Name: Benzoic acid (E)-(R)-1-[(S)-2-((2S,3aR,5R,6S,7S,7aR)-6,7-diacetoxy-5-acetoxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-2-yloxy)-1-hexadecanoylamino-ethyl]-hexadec-2-enyl ester
• CAS No.: 124338-03-0
• Molecular Formula: C₅₅H₈₉NO₁₃
• Molecular Weight: 972.311

Synonyms:

Chemical Property of Benzoic acid (E)-(R)-1-[(S)-2-((2S,3aR,5R,6S,7S,7aR)-6,7-diacetoxy-5-acetoxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-2-yloxy)-1-hexadecanoylamino-ethyl]-hexadec-2-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (E)-(R)-1-[(S)-2-((2S,3aR,5R,6S,7S,7aR)-6,7-diacetoxy-5-acetoxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-2-yloxy)-1-hexadecanoylamino-ethyl]-hexadec-2-enyl ester

There total 11 articles about Benzoic acid (E)-(R)-1-[(S)-2-((2S,3aR,5R,6S,7S,7aR)-6,7-diacetoxy-5-acetoxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-2-yloxy)-1-hexadecanoylamino-ethyl]-hexadec-2-enyl 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:

4-nitrophenyl palmitate (1492-30-4) → Benzoic acid (E)-(R)-1-[(S)-2-((2S,3aR,5R,6S,7S,7aR)-6,7-diacetoxy-5-acetoxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-2-yloxy)-1-hexadecanoylamino-ethyl]-hexadec-2-enyl ester (124338-03-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / pyridine / Ambient temperature

2: 72 percent / hydrochloric acid / tetrahydrofuran / 1 h / Heating

3: 66 percent / imidazole / dimethylformamide / 13 h / 60 °C

4: 89 percent / pyridine / 0.5 h / Ambient temperature

5: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

6: mercury(II) cyanide / nitromethane / 2 h / 80 °C

With pyridine; 1H-imidazole; hydrogenchloride; tetrabutyl ammonium fluoride; mercury(II) cyanide; In tetrahydrofuran; nitromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)80087-9

Reference yield:

(2S,3R,4E)-2-(hexadecanoylamido)-4-octadecene-1,3-diol (4201-58-5,4201-59-6,24696-34-2,52019-77-9,74743-19-4,102917-79-3,24696-26-2) → Benzoic acid (E)-(R)-1-[(S)-2-((2S,3aR,5R,6S,7S,7aR)-6,7-diacetoxy-5-acetoxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-2-yloxy)-1-hexadecanoylamino-ethyl]-hexadec-2-enyl ester (124338-03-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent / imidazole / dimethylformamide / 13 h / 60 °C

2: 89 percent / pyridine / 0.5 h / Ambient temperature

3: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

4: mercury(II) cyanide / nitromethane / 2 h / 80 °C

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; mercury(II) cyanide; In tetrahydrofuran; nitromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)80087-9

Reference yield:

(2R,3R)-trans-2-azide-1,3-O-benzylidene-1,3-octadec-4-enediol (114275-40-0) → Benzoic acid (E)-(R)-1-[(S)-2-((2S,3aR,5R,6S,7S,7aR)-6,7-diacetoxy-5-acetoxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-2-yloxy)-1-hexadecanoylamino-ethyl]-hexadec-2-enyl ester (124338-03-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 99.5 percent / triphenylphosphine / tetrahydrofuran; H₂O / Ambient temperature

2: 95 percent / pyridine / Ambient temperature

3: 72 percent / hydrochloric acid / tetrahydrofuran / 1 h / Heating

4: 66 percent / imidazole / dimethylformamide / 13 h / 60 °C

5: 89 percent / pyridine / 0.5 h / Ambient temperature

6: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

7: mercury(II) cyanide / nitromethane / 2 h / 80 °C

With pyridine; 1H-imidazole; hydrogenchloride; tetrabutyl ammonium fluoride; triphenylphosphine; mercury(II) cyanide; In tetrahydrofuran; nitromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)80087-9

upstream raw materials:

(2S,3R,4E)-3-benzoyl-2-(hexadecanamido)-4-octadecene-1,3-diol

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

(2S,3R,4E)-2-(hexadecanoylamido)-4-octadecene-1,3-diol

4-nitrophenyl palmitate

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