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

Base Information

• Chemical Name: benzyl 2-<(3R)-3-(benzyloxymethoxy)tetradecanamido>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
• CAS No.: 111247-22-4
• Molecular Formula: C₃₈H₅₇NO₈
• Molecular Weight: 655.872
• Mol file: 111247-22-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about benzyl 2-<(3R)-3-(benzyloxymethoxy)tetradecanamido>-2-deoxy-4,6-O-isopropylidene-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: 81.0%

(3R)-3-(Benzyloxymethoxy)tetradecanoic acid (111247-11-1) + benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (102794-17-2) → benzyl 2-<(3R)-3-(benzyloxymethoxy)tetradecanamido>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (111247-22-4)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; Ambient temperature;

DOI:10.1271/bbb.59.1790

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → benzyl 2-<(3R)-3-(benzyloxymethoxy)tetradecanamido>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (111247-22-4)

Guidance literature:

Multi-step reaction with 3 steps

1: diisopropylethylamine / CH₂Cl₂ / Ambient temperature

2: zinc dust / acetic acid / 50 °C

3: 80.2 percent / DCC / CH₂Cl₂ / Ambient temperature

With 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 2-<(3R)-3-(benzyloxymethoxy)tetradecanamido>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (111247-22-4)

Guidance literature:

Multi-step reaction with 4 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

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

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

upstream raw materials:

(3R)-3-(Benzyloxymethoxy)tetradecanoic acid

benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

Benzyloxymethyl chloride

(R)-3-hydroxytetradecanoic acid

Downstream raw materials:

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

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

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

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