methyl 3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-2-<(E)-tetradec-2-enamido>-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-2-<(E)-tetradec-2-enamido>-β-D-glucopyranoside
• CAS No.: 90176-40-2
• Molecular Formula: C₃₇H₅₂NO₁₁P
• Molecular Weight: 717.794

Synonyms:methyl 3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-2-<(E)-tetradec-2-enamido>-β-D-glucopyranoside

Chemical Property of methyl 3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-2-<(E)-tetradec-2-enamido>-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-2-<(E)-tetradec-2-enamido>-β-D-glucopyranoside

There total 13 articles about methyl 3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-2-<(E)-tetradec-2-enamido>-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: 67.0%

methanol (67-56-1) + 2'-<(2RS)-2-acetoxytridecyl>-3,6-di-O-acetyl-1,2-dideoxy-4-O-diphenylphosphono-α-D-glucopyranoso<2.1-d>-Δ2-oxazoline (88862-76-4,90243-20-2) → methyl 3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-2-<(E)-tetradec-2-enamido>-β-D-glucopyranoside (90176-40-2)

Guidance literature:

With toluene-4-sulfonic acid; In nitromethane; toluene; at 35 ℃; for 1h;

DOI:10.1039/P19840000275

Reference yield:

(R)-3-hydroxytetradecanoic acid (28715-21-1,3422-31-9) → methyl 3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-2-<(E)-tetradec-2-enamido>-β-D-glucopyranoside (90176-40-2)

Guidance literature:

Multi-step reaction with 8 steps

1: Et₃N, NN-dicyclohexylcarbodi-imide / pyridine

2: NaOAc / 1 h / 100 °C

3: 41 percent / H₂ / 10percent palladium-charcoal / ethanol / 50 °C

4: 50 percent / pyridine / CH₂Cl₂ / -30 deg C -> room temperature, overnight

5: 85 percent / pyridine, 4-dimethylaminopyridine / benzene

6: 33percent HBr-AcOH, Ac₂O / CHCl₃ / 1 h / Ambient temperature

7: Hg(CN)2, 2-<(3R)-3-acetoxytetradecanamido>-1,3-di-O-acetyl-2-deoxy-β-D-glucopyranose / nitromethane; toluene / 72 h

8: 67 percent / toluene-p-sulphonic acid / toluene; nitromethane / 1 h / 35 °C

With pyridine; dmap; hydrogen bromide; hydrogen; sodium acetate; mercury(II) cyanide; acetic anhydride; toluene-4-sulfonic acid; acetic acid; 2-<(3R)-3-acetoxytetradecanamido>-1,3-di-O-acetyl-2-deoxy-β-D-glucopyranose; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In pyridine; nitromethane; ethanol; dichloromethane; chloroform; toluene; benzene;

DOI:10.1039/P19840000275

Reference yield:

2-benzylideneamino-2-deoxy-β-D-glucopyranose (90176-39-9) → methyl 3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-2-<(E)-tetradec-2-enamido>-β-D-glucopyranoside (90176-40-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 73 percent / ZnCl₂ / 53 h / Ambient temperature

2: 90 percent / pyridine

3: 80 percent / 5M HCl / acetone / 0.25 h / ice-bath

4: Et₃N, NN-dicyclohexylcarbodi-imide / pyridine

5: NaOAc / 1 h / 100 °C

6: 41 percent / H₂ / 10percent palladium-charcoal / ethanol / 50 °C

7: 50 percent / pyridine / CH₂Cl₂ / -30 deg C -> room temperature, overnight

8: 85 percent / pyridine, 4-dimethylaminopyridine / benzene

9: 33percent HBr-AcOH, Ac₂O / CHCl₃ / 1 h / Ambient temperature

10: Hg(CN)2, 2-<(3R)-3-acetoxytetradecanamido>-1,3-di-O-acetyl-2-deoxy-β-D-glucopyranose / nitromethane; toluene / 72 h

11: 67 percent / toluene-p-sulphonic acid / toluene; nitromethane / 1 h / 35 °C

With pyridine; hydrogenchloride; dmap; hydrogen bromide; hydrogen; sodium acetate; mercury(II) cyanide; acetic anhydride; toluene-4-sulfonic acid; acetic acid; 2-<(3R)-3-acetoxytetradecanamido>-1,3-di-O-acetyl-2-deoxy-β-D-glucopyranose; triethylamine; dicyclohexyl-carbodiimide; zinc(II) chloride; palladium on activated charcoal; In pyridine; nitromethane; ethanol; dichloromethane; chloroform; acetone; toluene; benzene;

DOI:10.1039/P19840000275

upstream raw materials:

methanol

2'-<(2RS)-2-acetoxytridecyl>-3,6-di-O-acetyl-1,2-dideoxy-4-O-diphenylphosphono-α-D-glucopyranoso<2.1-d>-Δ²-oxazoline

(R)-3-hydroxytetradecanoic acid

2-<(3R)-3-acetoxytetradecanamido>-3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-α-D-glucopyranosyl bromide

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 90176-40-2 methyl 3,6-di-O-acetyl-2-deoxy-4-O-diphenylphosphono-2-<(E)-tetradec-2-enamido>-β-D-glucopyranoside

Send

Send

Metric Ton KG G Pound L ML

Send

Send