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

Base Information

• Chemical Name: methyl S-4-methylphenyl 5-acetamido-4,7-di-O-acetyl-3,5-dideoxy-8,9-O-isopropylidene-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonate
• CAS No.: 381715-80-6
• Molecular Formula: C₂₆H₃₅NO₁₀S
• Molecular Weight: 553.631
• Mol file: 381715-80-6.mol

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

Chemical Property of methyl S-4-methylphenyl 5-acetamido-4,7-di-O-acetyl-3,5-dideoxy-8,9-O-isopropylidene-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl S-4-methylphenyl 5-acetamido-4,7-di-O-acetyl-3,5-dideoxy-8,9-O-isopropylidene-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonate

There total 5 articles about methyl S-4-methylphenyl 5-acetamido-4,7-di-O-acetyl-3,5-dideoxy-8,9-O-isopropylidene-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonate 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-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3) → methyl S-4-methylphenyl 5-acetamido-4,7-di-O-acetyl-3,5-dideoxy-8,9-O-isopropylidene-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonate (381715-80-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / aq. NaOH; BnEt₃NCl / CHCl₃ / 0.5 h / Heating

2: NaOMe / methanol / 1 h / 20 °C

3: CSA / acetone / 1 h / 20 °C

4: 0.320 g / Py

With pyridine; sodium hydroxide; camphor-10-sulfonic acid; N-benzyl-N,N,N-triethylammonium chloride; sodium methylate; In methanol; chloroform; acetone;

DOI:10.1021/ja011382r

Reference yield:

para-thiocresol (106-45-6) → methyl S-4-methylphenyl 5-acetamido-4,7-di-O-acetyl-3,5-dideoxy-8,9-O-isopropylidene-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonate (381715-80-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / aq. NaOH; BnEt₃NCl / CHCl₃ / 0.5 h / Heating

2: NaOMe / methanol / 1 h / 20 °C

3: CSA / acetone / 1 h / 20 °C

4: 0.320 g / Py

With pyridine; sodium hydroxide; camphor-10-sulfonic acid; N-benzyl-N,N,N-triethylammonium chloride; sodium methylate; In methanol; chloroform; acetone;

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) → methyl S-4-methylphenyl 5-acetamido-4,7-di-O-acetyl-3,5-dideoxy-8,9-O-isopropylidene-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonate (381715-80-6)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOMe / methanol / 1 h / 20 °C

2: CSA / acetone / 1 h / 20 °C

3: 0.320 g / Py

With pyridine; camphor-10-sulfonic acid; sodium methylate; In methanol; acetone;

DOI:10.1021/ja011382r

upstream raw materials:

acetic anhydride

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

para-thiocresol

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

Downstream raw materials:

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

methyl S-4-methylphenyl 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-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonate

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