Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-tetracosanoylamino-tridecyloxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-tetracosanoylamino-tridecyloxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 791611-43-3
• Molecular Formula: C₆₀H₁₀₁NO₁₄
• Molecular Weight: 1060.46

Synonyms:Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-tetracosanoylamino-tridecyloxy)-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-tetracosanoylamino-tridecyloxy)-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-tetracosanoylamino-tridecyloxy)-tetrahydro-pyran-4-yl ester

There total 9 articles about Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-tetracosanoylamino-tridecyloxy)-tetrahydro-pyran-4-yl 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: 80.0%

3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-galactopyranosyl bromide (53872-78-9) + Acetic acid (1S,2R)-2-acetoxy-1-((S)-2-hydroxy-1-tetracosanoylamino-ethyl)-undecyl ester (791611-37-5) → Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-tetracosanoylamino-tridecyloxy)-tetrahydro-pyran-4-yl ester (791611-43-3)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; for 4h;

DOI:10.1021/ja045385q

Reference yield:

n-tetracosanoic acid (557-59-5) → Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-tetracosanoylamino-tridecyloxy)-tetrahydro-pyran-4-yl ester (791611-43-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N-hydroxysuccinimide; DCC / tetrahydrofuran / 3 h / Heating

1.2: Et₃N / tetrahydrofuran / 3 h / Heating

2.1: imidazole / tetrahydrofuran / 0.08 h / 50 °C

3.1: DMAP; Et₃N / tetrahydrofuran / 2 h / 20 °C

4.1: 54 mg / aq. HF / tetrahydrofuran

5.1: 80 percent / AgOTf; molecular sieves 4A / CH₂Cl₂ / 4 h

With 1H-imidazole; dmap; 1-hydroxy-pyrrolidine-2,5-dione; 4 A molecular sieve; hydrogen fluoride; silver trifluoromethanesulfonate; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja045385q

Reference yield:

O2-benzyl-O3,O4-isopropyliden-1,6-anhydro-β-D-galactopyranose (55287-62-2) → Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-tetracosanoylamino-tridecyloxy)-tetrahydro-pyran-4-yl ester (791611-43-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / trifluoroacetic acid / 0 - 20 °C

2: 75 percent / HBr; AcOH / CH₂Cl₂ / 12 h / 4 °C

3: 80 percent / AgOTf; molecular sieves 4A / CH₂Cl₂ / 4 h

With 4 A molecular sieve; hydrogen bromide; silver trifluoromethanesulfonate; acetic acid; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ja045385q

upstream raw materials:

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

Acetic acid (1S,2R)-2-acetoxy-1-((S)-2-hydroxy-1-tetracosanoylamino-ethyl)-undecyl ester

n-tetracosanoic acid

O²-benzyl-O³,O⁴-isopropyliden-1,6-anhydro-β-D-galactopyranose

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