(S)-3-Benzyloxymethoxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-5-hydroxy-3-((S)-3-tetradecanoyloxy-tetradecanoylamino)-6-trityloxymethyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: (S)-3-Benzyloxymethoxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-5-hydroxy-3-((S)-3-tetradecanoyloxy-tetradecanoylamino)-6-trityloxymethyl-tetrahydro-pyran-4-yl ester
• CAS No.: 111247-18-8
• Molecular Formula: C₈₂H₁₁₉NO₁₁
• Molecular Weight: 1294.85
• Mol file: 111247-18-8.mol

Synonyms:

Chemical Property of (S)-3-Benzyloxymethoxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-5-hydroxy-3-((S)-3-tetradecanoyloxy-tetradecanoylamino)-6-trityloxymethyl-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-Benzyloxymethoxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-5-hydroxy-3-((S)-3-tetradecanoyloxy-tetradecanoylamino)-6-trityloxymethyl-tetrahydro-pyran-4-yl ester

There total 11 articles about (S)-3-Benzyloxymethoxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-5-hydroxy-3-((S)-3-tetradecanoyloxy-tetradecanoylamino)-6-trityloxymethyl-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:

(3S)-3-hydroxytetradecanoic acid phenacyl ester (111247-10-0) → (S)-3-Benzyloxymethoxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-5-hydroxy-3-((S)-3-tetradecanoyloxy-tetradecanoylamino)-6-trityloxymethyl-tetrahydro-pyran-4-yl ester (111247-18-8)

Guidance literature:

Multi-step reaction with 5 steps

1: diisopropylethylamine / CH₂Cl₂ / Ambient temperature

2: zinc dust / acetic acid / 50 °C

3: DCC, DMAP / CH₂Cl₂ / Ambient temperature

4: aqueous acetic acid / 3 h / 45 °C

5: pyridine / 5 h / 90 °C

With dmap; acetic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; zinc; In pyridine; dichloromethane; acetic acid;

DOI:10.1016/0008-6215(87)80207-0

Reference yield:

(3S)-3-hydroxytetradecanoic acid (35683-15-9,3422-31-9) → (S)-3-Benzyloxymethoxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-5-hydroxy-3-((S)-3-tetradecanoyloxy-tetradecanoylamino)-6-trityloxymethyl-tetrahydro-pyran-4-yl ester (111247-18-8)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine / ethyl acetate / 6 h / Ambient temperature

2: diisopropylethylamine / CH₂Cl₂ / Ambient temperature

3: zinc dust / acetic acid / 50 °C

4: DCC, DMAP / CH₂Cl₂ / Ambient temperature

5: aqueous acetic acid / 3 h / 45 °C

6: pyridine / 5 h / 90 °C

With dmap; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; zinc; In pyridine; dichloromethane; acetic acid; ethyl acetate;

DOI:10.1016/0008-6215(87)80207-0

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (S)-3-Benzyloxymethoxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-5-hydroxy-3-((S)-3-tetradecanoyloxy-tetradecanoylamino)-6-trityloxymethyl-tetrahydro-pyran-4-yl ester (111247-18-8)

Guidance literature:

Multi-step reaction with 5 steps

1: diisopropylethylamine / CH₂Cl₂ / Ambient temperature

2: zinc dust / acetic acid / 50 °C

3: DCC, DMAP / CH₂Cl₂ / Ambient temperature

4: aqueous acetic acid / 3 h / 45 °C

5: pyridine / 5 h / 90 °C

With dmap; acetic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; zinc; In pyridine; dichloromethane; acetic acid;

DOI:10.1016/0008-6215(87)80207-0

upstream raw materials:

trityl chloride

(S)-3-Benzyloxymethoxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-benzyloxy-5-hydroxy-6-hydroxymethyl-3-((S)-3-tetradecanoyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester

Benzyloxymethyl chloride

(3S)-3-hydroxytetradecanoic acid

Downstream raw materials:

benzyl 3-O-<(3S)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-4-O-(diphenylphosphono)-2-<(3S)-3-tetradecanoyloxytetradecanamido>-β-D-glucopyranoside