Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-[[(R)-3-[((E)-propenyl)oxy]-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propoxy]-(2,2,2-tribromo-ethoxy)-phosphoryloxy]-ethyl ester

Base Information

• Chemical Name: Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-[[(R)-3-[((E)-propenyl)oxy]-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propoxy]-(2,2,2-tribromo-ethoxy)-phosphoryloxy]-ethyl ester
• CAS No.: 73485-64-0
• Molecular Formula: C₇₇H₁₁₄Br₃O₁₅P
• Molecular Weight: 1550.43

Synonyms:

Chemical Property of Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-[[(R)-3-[((E)-propenyl)oxy]-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propoxy]-(2,2,2-tribromo-ethoxy)-phosphoryloxy]-ethyl ester

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Technology Process of Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-[[(R)-3-[((E)-propenyl)oxy]-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propoxy]-(2,2,2-tribromo-ethoxy)-phosphoryloxy]-ethyl ester

There total 14 articles about Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-[[(R)-3-[((E)-propenyl)oxy]-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propoxy]-(2,2,2-tribromo-ethoxy)-phosphoryloxy]-ethyl 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: 83.0%

1,2-di-O-palmitoyl-sn-glycero-3-phospho-(2,2,2-tribromoethanol) (73485-62-8) + (R)-3-[((E)-Propenyl)oxy]-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propan-1-ol (81703-30-2) → Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-[[(S)-3-[((E)-propenyl)oxy]-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propoxy]-(2,2,2-tribromo-ethoxy)-phosphoryloxy]-ethyl ester (73485-64-0,81703-31-3)

Guidance literature:

With 2,2,2-triisopropylbenzenesulphonyl-3-nitro-1,2,4-triazole; In pyridine; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)98907-0

Reference yield: 83.0%

1,2-di-O-palmitoyl-sn-glycero-3-phospho-(2,2,2-tribromoethanol) (73485-62-8) + 1-O-(prop-1-enyl)-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol (73485-59-3) → Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-[[(R)-3-[((E)-propenyl)oxy]-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propoxy]-(2,2,2-tribromo-ethoxy)-phosphoryloxy]-ethyl ester (73485-64-0,81703-31-3)

Guidance literature:

With 2,2,2-triisopropylbenzenesulphonyl-3-nitro-1,2,4-triazole; In pyridine; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)98907-0

Reference yield:

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 4-nitrobenzoate (4196-36-5) → Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-[[(R)-3-[((E)-propenyl)oxy]-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propoxy]-(2,2,2-tribromo-ethoxy)-phosphoryloxy]-ethyl ester (73485-64-0,81703-31-3)

Guidance literature:

Multi-step reaction with 5 steps

1: HBr / CH₂Cl₂ / 0.17 h / Ambient temperature

2: 60 percent / di-isopropyl-ethylamine / tetraethylammonium bromide / CH₂Cl₂; dimethylformamide / 96 h / Ambient temperature

3: 87 percent / tetrabutylammonium hydroxide / H₂O; dioxane / 4 h / 20 °C

4: 96 percent / DABCO / (Ph₃P)3RhCl / ethanol; H₂O / 2.5 h / 85 °C

5: 83 percent / 2,2,2-triisopropylbenzenesulphonyl-3-nitro-1,2,4-triazole / pyridine / 2 h / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; 2,2,2-triisopropylbenzenesulphonyl-3-nitro-1,2,4-triazole; tetra(n-butyl)ammonium hydroxide; hydrogen bromide; N-ethyl-N,N-diisopropylamine; Wilkinson's catalyst; tetraethylammonium bromide; In 1,4-dioxane; pyridine; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)98907-0

upstream raw materials:

1,2-di-O-palmitoyl-sn-glycero-3-phospho-(2,2,2-tribromoethanol)

(R)-3-[((E)-Propenyl)oxy]-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propan-1-ol

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 4-nitrobenzoate

Downstream raw materials:

Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-[[(S)-3-hydroxy-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propoxy]-(2,2,2-tribromo-ethoxy)-phosphoryloxy]-ethyl ester

Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-[[(R)-3-hydroxy-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propoxy]-(2,2,2-tribromo-ethoxy)-phosphoryloxy]-ethyl ester

Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-{hydroxy-[(R)-3-hydroxy-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propoxy]-phosphoryloxy}-ethyl ester

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