methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-2,5-dideoxy-D-erythro-α-L-gluco-non-2-ulopyranosonate

Base Information

• Chemical Name: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-2,5-dideoxy-D-erythro-α-L-gluco-non-2-ulopyranosonate
• CAS No.: 942043-18-7
• Molecular Formula: C₃₄H₃₂O₇S
• Molecular Weight: 584.69
• Mol file: 942043-18-7.mol

Synonyms:methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-2,5-dideoxy-D-erythro-α-L-gluco-non-2-ulopyranosonate

Chemical Property of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-2,5-dideoxy-D-erythro-α-L-gluco-non-2-ulopyranosonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-2,5-dideoxy-D-erythro-α-L-gluco-non-2-ulopyranosonate

There total 3 articles about methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-2,5-dideoxy-D-erythro-α-L-gluco-non-2-ulopyranosonate 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: 96.0%

p-methylphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (220645-45-4) → methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-2,5-dideoxy-D-erythro-α-L-gluco-non-2-ulopyranosonate (942043-18-7)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In tetrahydrofuran; at 20 ℃; for 8h; Inert atmosphere;

Reference yield: 96.0%

C34H30O7S → methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-2,5-dideoxy-D-erythro-α-L-gluco-non-2-ulopyranosonate (942043-18-7)

Guidance literature:

With borane-THF; copper(II) bis(trifluoromethanesulfonate); In tetrahydrofuran; at 20 ℃; for 8h;

DOI:10.1021/jacs.9b01991

Reference yield: 56.0%

4-methylphenyl 2,3,4,6-tetrakis-O-(trimethylsilyl)-1-thio-β-D-galactopyranoside + benzaldehyde (100-52-7) + benzoic acid anhydride (93-97-0) → methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-2,5-dideoxy-D-erythro-α-L-gluco-non-2-ulopyranosonate (942043-18-7)

Guidance literature:

4-methylphenyl 2,3,4,6-tetrakis-O-(trimethylsilyl)-1-thio-β-D-galactopyranoside; benzaldehyde; trimethylsilyl trifluoromethanesulfonate;

benzoic acid anhydride;

With borane-THF;

upstream raw materials:

benzaldehyde

benzoic acid anhydride

p-methylphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Downstream raw materials:

4-methylphenyl 6-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-phthalimido-D-glycero-β-D-galacto-2-nonulopyranosylonate)-2,3-di-O-benzoyl-4-benzyl-1-thio-α-D-galactopyranoside

4-methylphenyl 6-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-phthalimido-D-glycero-α-D-galacto-2-nonulopyranosylonate)-2,3-di-O-benzoyl-4-benzyl-1-thio-α-D-galactopyranoside