allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside
• CAS No.: 114360-80-4
• Molecular Formula: C₆₄H₉₈N₂O₁₃
• Molecular Weight: 1103.49
• Mol file: 114360-80-4.mol

Synonyms:allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside

Chemical Property of allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside

There total 15 articles about allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-2-deoxy-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: 84.0%

allyl 6-O-<3,4,6-tri-O-acetyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranoside (92949-55-8) → allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside (114360-80-4)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; for 5h; Ambient temperature;

DOI:10.1246/bcsj.60.2197

Reference yield:

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline (10378-06-0,20757-53-3,35954-65-5,123483-77-2,134308-33-1) → allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside (114360-80-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / p-toluenesulfonic acid / CHCl₃ / 7 h / Heating

2: 1.) potassium carbonate, triethyloxonium tetrafluoroborate, 2.) 1 M hydrochloric acid / 1.) CH₂Cl₂, 13 h, room temp. 2.) THF, 3 h, room temp.

3: 5.8 g / dicyclohexylcarbodiimide / tetrahydrofuran / 19 h / Ambient temperature

4: 84 percent / 1 M sodium methoxide / methanol; tetrahydrofuran / 5 h / Ambient temperature

With hydrogenchloride; sodium methylate; triethyloxonium fluoroborate; potassium carbonate; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; chloroform;

DOI:10.1246/bcsj.60.2197

Reference yield:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside (114360-80-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) trifluoromethanesulfonic acid, 2.) 1M hydrochloric acid, 3.) acetic anhydride, triethylamine / 1.) CH₂Cl₂, 4 deg C, 2.) THF, room temp. 3.) THF, room temp.

2: 79 percent / 0.02 M sodium methoxyde / 6 h / 0 °C

3: 64 percent / p-toluenesulfonic acid / CHCl₃ / 7 h / Heating

4: 1.) potassium carbonate, triethyloxonium tetrafluoroborate, 2.) 1 M hydrochloric acid / 1.) CH₂Cl₂, 13 h, room temp. 2.) THF, 3 h, room temp.

5: 5.8 g / dicyclohexylcarbodiimide / tetrahydrofuran / 19 h / Ambient temperature

6: 84 percent / 1 M sodium methoxide / methanol; tetrahydrofuran / 5 h / Ambient temperature

With hydrogenchloride; trifluorormethanesulfonic acid; sodium methylate; triethyloxonium fluoroborate; acetic anhydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; chloroform;

DOI:10.1246/bcsj.60.2197

upstream raw materials:

allyl 6-O-<3,4,6-tri-O-acetyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranoside

allyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranoside

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside

2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate

Downstream raw materials:

allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside