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

Base Information

• Chemical Name: benzyl-<(3R)-3-(benzyloxymethoxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-4-O-(diphenylphosphono)-β-D-glucopyranoside
• CAS No.: 112475-26-0
• Molecular Formula: C₆₉H₉₆NO₁₄P
• Molecular Weight: 1194.49

Synonyms:benzyl-<(3R)-3-(benzyloxymethoxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-4-O-(diphenylphosphono)-β-D-glucopyranoside

Chemical Property of benzyl-<(3R)-3-(benzyloxymethoxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-4-O-(diphenylphosphono)-β-D-glucopyranoside

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Technology Process of benzyl-<(3R)-3-(benzyloxymethoxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-4-O-(diphenylphosphono)-β-D-glucopyranoside

There total 10 articles about benzyl-<(3R)-3-(benzyloxymethoxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-4-O-(diphenylphosphono)-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:

Benzyloxymethyl chloride (3587-60-8) → benzyl-<(3R)-3-(benzyloxymethoxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-4-O-(diphenylphosphono)-β-D-glucopyranoside (112475-26-0)

Guidance literature:

Multi-step reaction with 7 steps

1: diisopropylethylamine / CH₂Cl₂ / Ambient temperature

2: zinc dust / acetic acid / 50 °C

3: 80.2 percent / DCC / CH₂Cl₂ / Ambient temperature

4: 98.6 percent / DCC, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

5: 91 percent / acetic acid, water / 3 h / 45 °C

6: 88 percent / pyridine / 5 h / 90 °C

7: 1) DMAP, pyridine 2) tetrafluoroboric acid / 1) methylene dichloride 2) acetonitrile

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

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

Reference yield:

(R)-3-hydroxytetradecanoic acid (28715-21-1,3422-31-9) → benzyl-<(3R)-3-(benzyloxymethoxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-4-O-(diphenylphosphono)-β-D-glucopyranoside (112475-26-0)

Guidance literature:

Multi-step reaction with 8 steps

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

2: diisopropylethylamine / CH₂Cl₂ / Ambient temperature

3: zinc dust / acetic acid / 50 °C

4: 80.2 percent / DCC / CH₂Cl₂ / Ambient temperature

5: 98.6 percent / DCC, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

6: 91 percent / acetic acid, water / 3 h / 45 °C

7: 88 percent / pyridine / 5 h / 90 °C

8: 1) DMAP, pyridine 2) tetrafluoroboric acid / 1) methylene dichloride 2) acetonitrile

With pyridine; dmap; tetrafluoroboric acid; water; acetic acid; 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:

(3R)-3-(Benzyloxymethoxy)tetradecanoic acid (111247-11-1) → benzyl-<(3R)-3-(benzyloxymethoxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-4-O-(diphenylphosphono)-β-D-glucopyranoside (112475-26-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 80.2 percent / DCC / CH₂Cl₂ / Ambient temperature

2: 98.6 percent / DCC, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

3: 91 percent / acetic acid, water / 3 h / 45 °C

4: 88 percent / pyridine / 5 h / 90 °C

5: 1) DMAP, pyridine 2) tetrafluoroboric acid / 1) methylene dichloride 2) acetonitrile

With pyridine; dmap; tetrafluoroboric acid; water; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane;

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

upstream raw materials:

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

chlorophosphoric acid diphenyl ester

Benzyloxymethyl chloride

(R)-3-hydroxytetradecanoic acid

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