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

Base Information

• Chemical Name: benzyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-4-O-(diphenylphosphono)-2-<(3R)-3-dodecanoyloxytetradecanamido>-β-D-glucopyranoside
• CAS No.: 112166-27-5
• Molecular Formula: C₇₃H₁₁₀NO₁₄P
• Molecular Weight: 1256.65

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

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

There total 8 articles about benzyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-4-O-(diphenylphosphono)-2-<(3R)-3-dodecanoyloxytetradecanamido>-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:

n-dodecanoyl chloride (112-16-3) → benzyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-4-O-(diphenylphosphono)-2-<(3R)-3-dodecanoyloxytetradecanamido>-β-D-glucopyranoside (112166-27-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 95.3 percent / DMAP / CH₂Cl₂; pyridine / Ambient temperature

2: zinc dust, acetic acid / 50 °C

3: 90 percent / 3-(3-dimethylamino)propyl-1-ethylcarbodiimide hydrochloride / CH₂Cl₂ / Ambient temperature

4: 98.2 percent / 3-(3-dimethylamino)propyl-1-ethylcarbodiimide hydrochloride, 4-(dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

5: 94.5 percent / 95percent acetic acid

6: 91 percent / pyridine / 6 h / 90 °C

7: 1.) 4-(dimethylamino)pyridine / 1.) CH₂Cl₂, pyridine; 2.) detritylation

With dmap; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; In pyridine; dichloromethane;

DOI:10.1016/0008-6215(87)80220-3

Reference yield:

C26H50O4 (107856-74-6) → benzyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-4-O-(diphenylphosphono)-2-<(3R)-3-dodecanoyloxytetradecanamido>-β-D-glucopyranoside (112166-27-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / 3-(3-dimethylamino)propyl-1-ethylcarbodiimide hydrochloride / CH₂Cl₂ / Ambient temperature

2: 98.2 percent / 3-(3-dimethylamino)propyl-1-ethylcarbodiimide hydrochloride, 4-(dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

3: 94.5 percent / 95percent acetic acid

4: 91 percent / pyridine / 6 h / 90 °C

5: 1.) 4-(dimethylamino)pyridine / 1.) CH₂Cl₂, pyridine; 2.) detritylation

With dmap; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In pyridine; dichloromethane;

DOI:10.1016/0008-6215(87)80220-3

Reference yield:

(3R)-3-hydroxytetradecanoic acid phenacyl ester (87357-65-1) → benzyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-4-O-(diphenylphosphono)-2-<(3R)-3-dodecanoyloxytetradecanamido>-β-D-glucopyranoside (112166-27-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 95.3 percent / DMAP / CH₂Cl₂; pyridine / Ambient temperature

2: zinc dust, acetic acid / 50 °C

3: 90 percent / 3-(3-dimethylamino)propyl-1-ethylcarbodiimide hydrochloride / CH₂Cl₂ / Ambient temperature

4: 98.2 percent / 3-(3-dimethylamino)propyl-1-ethylcarbodiimide hydrochloride, 4-(dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

5: 94.5 percent / 95percent acetic acid

6: 91 percent / pyridine / 6 h / 90 °C

7: 1.) 4-(dimethylamino)pyridine / 1.) CH₂Cl₂, pyridine; 2.) detritylation

With dmap; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; In pyridine; dichloromethane;

DOI:10.1016/0008-6215(87)80220-3

upstream raw materials:

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

chlorophosphoric acid diphenyl ester

n-dodecanoyl chloride

C₂₆H₅₀O₄

Downstream raw materials:

(R)-3-Hydroxy-tetradecanoic acid (2R,3S,4R,5R)-3-(diphenoxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-hydroxy-2-hydroxymethyl-tetrahydro-pyran-4-yl ester

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