benzyl 2-<(3S)-3-(benzyloxymethoxy)tetradecanamido>-2-deoxy-4,6-O-isopropylidene-3-O-<(3S)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2-<(3S)-3-(benzyloxymethoxy)tetradecanamido>-2-deoxy-4,6-O-isopropylidene-3-O-<(3S)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranoside
• CAS No.: 111247-25-7
• Molecular Formula: C₆₆H₁₀₉NO₁₁
• Molecular Weight: 1092.59
• Mol file: 111247-25-7.mol

Synonyms:

Chemical Property of benzyl 2-<(3S)-3-(benzyloxymethoxy)tetradecanamido>-2-deoxy-4,6-O-isopropylidene-3-O-<(3S)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-<(3S)-3-(benzyloxymethoxy)tetradecanamido>-2-deoxy-4,6-O-isopropylidene-3-O-<(3S)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranoside

There total 8 articles about benzyl 2-<(3S)-3-(benzyloxymethoxy)tetradecanamido>-2-deoxy-4,6-O-isopropylidene-3-O-<(3S)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranoside 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) → benzyl 2-<(3S)-3-(benzyloxymethoxy)tetradecanamido>-2-deoxy-4,6-O-isopropylidene-3-O-<(3S)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranoside (111247-25-7)

Guidance literature:

Multi-step reaction with 4 steps

1: diisopropylethylamine / CH₂Cl₂ / Ambient temperature

2: zinc dust / acetic acid / 50 °C

3: 84 percent / DCC / CH₂Cl₂ / Ambient temperature

4: DCC, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

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

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

Reference yield:

(3S)-3-hydroxytetradecanoic acid (35683-15-9,3422-31-9) → benzyl 2-<(3S)-3-(benzyloxymethoxy)tetradecanamido>-2-deoxy-4,6-O-isopropylidene-3-O-<(3S)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranoside (111247-25-7)

Guidance literature:

Multi-step reaction with 5 steps

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

2: diisopropylethylamine / CH₂Cl₂ / Ambient temperature

3: zinc dust / acetic acid / 50 °C

4: 84 percent / DCC / CH₂Cl₂ / Ambient temperature

5: DCC, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

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

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

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → benzyl 2-<(3S)-3-(benzyloxymethoxy)tetradecanamido>-2-deoxy-4,6-O-isopropylidene-3-O-<(3S)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranoside (111247-25-7)

Guidance literature:

Multi-step reaction with 4 steps

1: diisopropylethylamine / CH₂Cl₂ / Ambient temperature

2: zinc dust / acetic acid / 50 °C

3: 84 percent / DCC / CH₂Cl₂ / Ambient temperature

4: DCC, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

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

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

upstream raw materials:

(S)-3-(tetradecanoyloxy)tetradecanoic acid

benzyl 2-<(3S)-3-(benzyloxymethoxy)tetradecanamido>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

Benzyloxymethyl chloride

(3S)-3-hydroxytetradecanoic acid

Downstream raw materials:

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

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

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