dibenzyl [methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->9)-5-acetamido-4,7,8-tri-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate] phosphite

Base Information

• Chemical Name: dibenzyl [methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->9)-5-acetamido-4,7,8-tri-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate] phosphite
• CAS No.: 381716-34-3
• Molecular Formula: C₅₂H₆₇N₂O₂₆P
• Molecular Weight: 1167.08
• Mol file: 381716-34-3.mol

Synonyms:dibenzyl [methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->9)-5-acetamido-4,7,8-tri-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate] phosphite

Chemical Property of dibenzyl [methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->9)-5-acetamido-4,7,8-tri-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate] phosphite

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dibenzyl [methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->9)-5-acetamido-4,7,8-tri-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate] phosphite

There total 9 articles about dibenzyl [methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->9)-5-acetamido-4,7,8-tri-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate] phosphite 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: 100.0%

dibenzyl N,N-diethylphosphoramidite (67746-43-4) + methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->9)-5-acetamido-4,7,8-tri-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosonate (118283-37-7) → dibenzyl [methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->9)-5-acetamido-4,7,8-tri-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate] phosphite (381716-34-3)

Guidance literature:

With 1H-tetrazole; In acetonitrile; at -40 - 20 ℃; for 0.583333h;

DOI:10.1021/ja011382r

Reference yield:

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3) → dibenzyl [methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->9)-5-acetamido-4,7,8-tri-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate] phosphite (381716-34-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 75 percent / aq. NaOH; BnEt₃NCl / CHCl₃ / 0.5 h / Heating

2.1: NaOMe / methanol / 1 h / 20 °C

3.1: CSA / acetone / 1 h / 20 °C

4.1: 0.320 g / Py

5.1: 76 percent / aq. AcOH / 6 h / 50 °C

6.1: molecular sieves AW-300 / acetonitrile / 1 h / 20 °C

6.2: TMSOTf / acetonitrile / 0.17 h / -40 °C

7.1: 0.120 g / Pyr

8.1: 66 percent / aq. NBS / acetone / 2 h / 20 °C

9.1: 100 percent / 1H-tetrazole / acetonitrile / 0.58 h / -40 - 20 °C

With pyridine; 1H-tetrazole; sodium hydroxide; N-Bromosuccinimide; 3 A molecular sieve; camphor-10-sulfonic acid; N-benzyl-N,N,N-triethylammonium chloride; sodium methylate; acetic acid; In methanol; chloroform; acetone; acetonitrile;

DOI:10.1021/ja011382r

Reference yield:

methyl S-4-methylphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonate (167084-05-1) → dibenzyl [methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->9)-5-acetamido-4,7,8-tri-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate] phosphite (381716-34-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaOMe / methanol / 1 h / 20 °C

2.1: CSA / acetone / 1 h / 20 °C

3.1: 0.320 g / Py

4.1: 76 percent / aq. AcOH / 6 h / 50 °C

5.1: molecular sieves AW-300 / acetonitrile / 1 h / 20 °C

5.2: TMSOTf / acetonitrile / 0.17 h / -40 °C

6.1: 0.120 g / Pyr

7.1: 66 percent / aq. NBS / acetone / 2 h / 20 °C

8.1: 100 percent / 1H-tetrazole / acetonitrile / 0.58 h / -40 - 20 °C

With pyridine; 1H-tetrazole; N-Bromosuccinimide; 3 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; acetic acid; In methanol; acetone; acetonitrile;

DOI:10.1021/ja011382r

upstream raw materials:

dibenzyl N,N-diethylphosphoramidite

methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->9)-5-acetamido-4,7,8-tri-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosonate

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

methyl S-4-methylphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonate