Acetic acid (R)-1-((3E,7Z)-(1S,2R)-2-hydroxy-1-trityloxymethyl-heptadeca-3,7-dienylcarbamoyl)-pentadecyl ester

Base Information

• Chemical Name: Acetic acid (R)-1-((3E,7Z)-(1S,2R)-2-hydroxy-1-trityloxymethyl-heptadeca-3,7-dienylcarbamoyl)-pentadecyl ester
• CAS No.: 115523-77-8
• Molecular Formula: C₅₅H₈₁NO₅
• Molecular Weight: 836.252

Synonyms:Acetic acid (R)-1-((3E,7Z)-(1S,2R)-2-hydroxy-1-trityloxymethyl-heptadeca-3,7-dienylcarbamoyl)-pentadecyl ester

Chemical Property of Acetic acid (R)-1-((3E,7Z)-(1S,2R)-2-hydroxy-1-trityloxymethyl-heptadeca-3,7-dienylcarbamoyl)-pentadecyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Acetic acid (R)-1-((3E,7Z)-(1S,2R)-2-hydroxy-1-trityloxymethyl-heptadeca-3,7-dienylcarbamoyl)-pentadecyl ester

There total 21 articles about Acetic acid (R)-1-((3E,7Z)-(1S,2R)-2-hydroxy-1-trityloxymethyl-heptadeca-3,7-dienylcarbamoyl)-pentadecyl 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: 35.0%

trityl chloride (76-83-5) + Acetic acid (S)-1-((3E,7Z)-2-hydroxy-1-hydroxymethyl-heptadeca-3,7-dienylcarbamoyl)-pentadecyl ester (127716-20-5,127760-57-0,127760-58-1,127760-59-2) → Acetic acid (S)-1-((3E,7Z)-(1S,2R)-2-hydroxy-1-trityloxymethyl-heptadeca-3,7-dienylcarbamoyl)-pentadecyl ester (115648-55-0) + Acetic acid (R)-1-((3E,7Z)-(1S,2R)-2-hydroxy-1-trityloxymethyl-heptadeca-3,7-dienylcarbamoyl)-pentadecyl ester (115523-77-8) + Acetic acid (S)-1-((3E,7Z)-(1R,2S)-2-hydroxy-1-trityloxymethyl-heptadeca-3,7-dienylcarbamoyl)-pentadecyl ester (115648-56-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 96h; Ambient temperature;

DOI:10.1016/S0040-4020(01)89186-9

Reference yield: 29.0%

trityl chloride (76-83-5) + Acetic acid (R)-1-((3E,7Z)-2-hydroxy-1-hydroxymethyl-heptadeca-3,7-dienylcarbamoyl)-pentadecyl ester (127716-20-5,127760-57-0,127760-58-1,127760-59-2) → Acetic acid (R)-1-((3E,7Z)-(1S,2R)-2-hydroxy-1-trityloxymethyl-heptadeca-3,7-dienylcarbamoyl)-pentadecyl ester (115523-77-8) + Acetic acid (R)-1-((3E,7Z)-(1R,2S)-2-hydroxy-1-trityloxymethyl-heptadeca-3,7-dienylcarbamoyl)-pentadecyl ester (115589-64-5)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 72h; Ambient temperature;

DOI:10.1016/S0040-4020(01)89186-9

Reference yield:

(Z)-4-tetradecen-1-ol (40642-41-9) → Acetic acid (R)-1-((3E,7Z)-(1S,2R)-2-hydroxy-1-trityloxymethyl-heptadeca-3,7-dienylcarbamoyl)-pentadecyl ester (115523-77-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 76 percent / PDC / CH₂Cl₂ / 4 h / Heating

2: 62 percent / toluene / 15 h / Heating

3: 72 percent / triethylamine / 8 h / 0 °C

4: 34 percent / pyridinium p-toluenesulfonate / acetone / 2.5 h / Heating

5: 93 percent / triethylamine / 3 h / Heating

6: 81 percent / LiAlH₄ / tetrahydrofuran / 5 h / Ambient temperature

7: 99 percent / DCC, 1-hydroxybenztriazole / CH₂Cl₂ / 1.5 h / Ambient temperature

8: 89 percent / PPTS / methanol / 21.5 h / Ambient temperature

9: DMAP, triethylamine / CH₂Cl₂ / 96 h / Ambient temperature

With dmap; lithium aluminium tetrahydride; dipyridinium dichromate; pyridinium p-toluenesulfonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; triethylamine; acetone; toluene;

DOI:10.1016/S0040-4020(01)89186-9

upstream raw materials:

trityl chloride

Acetic acid (S)-1-((3E,7Z)-2-hydroxy-1-hydroxymethyl-heptadeca-3,7-dienylcarbamoyl)-pentadecyl ester

Acetic acid (R)-1-((3E,7Z)-2-hydroxy-1-hydroxymethyl-heptadeca-3,7-dienylcarbamoyl)-pentadecyl ester

(R)-(-)-2-hydroxyhexadecanoic acid

Downstream raw materials:

(R)-2-Hydroxy-hexadecanoic acid [(3E,7Z)-(1S,2R)-2-hydroxy-1-((3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadeca-3,7-dienyl]-amide

Benzoic acid (2E,6Z)-(R)-1-[(S)-1-((R)-2-acetoxy-hexadecanoylamino)-2-hydroxy-ethyl]-hexadeca-2,6-dienyl ester

(R)-2-Hydroxy-hexadecanoic acid ((1S,2R)-2-hydroxy-1-hydroxymethyl-heptadecyl)-amide

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