(5-N-acetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: (5-N-acetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside
• CAS No.: 381716-71-8
• Molecular Formula: C₂₄H₃₅NO₁₃S
• Molecular Weight: 577.607
• Mol file: 381716-71-8.mol

Synonyms:(5-N-acetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside

Chemical Property of (5-N-acetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5-N-acetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside

There total 14 articles about (5-N-acetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside 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:

4,7,8,9-tetra-O-acetyl-N-acetylneuraminic acid methyl ester (84380-10-9) → (5-N-acetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside (381716-71-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1H-tetrazole / acetonitrile

1.2: tBuOOH / acetonitrile

1.3: DBU / tetrahydrofuran

2.1: NaOMe / methanol

3.1: NaOH

4.1: Neisseria α(2,3)-sialyltransferase; alkaline phosphatase; aq. HEPES buffer / MgCl2; DTT / 48 h / 25 °C / pH 7.5

With 1H-tetrazole; sodium hydroxide; HEPES buffer; Neisseria α(2,3)-sialyltransferase; sodium methylate; alkaline phosphatase; DL-dithiothreitol; magnesium chloride; In methanol; acetonitrile;

DOI:10.1021/ja011382r

Reference yield:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-5-phosphonooxymethyl-tetrahydro-furan-3-yl ester (47653-57-6) → (5-N-acetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside (381716-71-8)

Guidance literature:

Multi-step reaction with 4 steps

1: dimethylformamide; acetonitrile

2: NaOMe / methanol

3: NaOH

4: Neisseria α(2,3)-sialyltransferase; alkaline phosphatase; aq. HEPES buffer / MgCl2; DTT / 48 h / 25 °C / pH 7.5

With sodium hydroxide; HEPES buffer; Neisseria α(2,3)-sialyltransferase; sodium methylate; alkaline phosphatase; DL-dithiothreitol; magnesium chloride; In methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja011382r

Reference yield:

(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{[(2R,3R,4R,5R)-3,4-diacetoxy-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryloxy}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester → (5-N-acetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside (381716-71-8)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOMe / methanol

2: NaOH

3: Neisseria α(2,3)-sialyltransferase; alkaline phosphatase; aq. HEPES buffer / MgCl2; DTT / 48 h / 25 °C / pH 7.5

With sodium hydroxide; HEPES buffer; Neisseria α(2,3)-sialyltransferase; sodium methylate; alkaline phosphatase; DL-dithiothreitol; magnesium chloride; In methanol;

DOI:10.1021/ja011382r

upstream raw materials:

p-methylphenyl-1-thio-β-D-galactopyranoside

cytidine-5'-monophosphono-N-acetylneuraminic acid

4,7,8,9-tetra-O-acetyl-N-acetylneuraminic acid methyl ester

Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-5-phosphonooxymethyl-tetrahydro-furan-3-yl ester

Downstream raw materials:

p-methylphenyl [methyl (5-N-acetyl-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate]-(2->3)-4,6-di-O-acetyl-1-thio-β-D-galactopyranoside

p-methylphenyl [methyl (5-N-acetyl-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate]-(2->3)-2,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside