methyl (phenyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate

Base Information

• Chemical Name: methyl (phenyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate
• CAS No.: 299179-55-8
• Molecular Formula: C₂₈H₃₇NO₁₂S
• Molecular Weight: 611.667
• Mol file: 299179-55-8.mol

Synonyms:methyl (phenyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate

Chemical Property of methyl (phenyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (phenyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate

There total 1 articles about methyl (phenyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate 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: 81.0%

butanoic acid anhydride (106-31-0) + acetic anhydride (108-24-7) + (4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (155155-64-9) → methyl (phenyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate (299179-55-8)

Guidance literature:

(4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester; With methanesulfonic acid; In methanol; for 24h; Heating;

butanoic acid anhydride; With triethylamine; at 0 - 20 ℃; pH=9 - 10;

acetic anhydride; In pyridine; at 0 - 20 ℃;

DOI:10.1080/07328300008544114

Reference yield: 55.0%

2-(trimethylsilyl)ethyl 4,6-di-O-benzylidene-β-D-galactopyranoside (117252-96-7) + methyl (phenyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate (299179-55-8) → 2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosulonate)-(2->3)-4,6-O-benzylidene-β-D-galactopyranoside

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 3 Angstroem MS; In acetonitrile; at -35 ℃;

DOI:10.1080/07328300008544114

Reference yield:

methyl (phenyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate (299179-55-8) → (methyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosulonate)-(2->3)-1-O-acetyl-2,4,6-tri-O-benzoyl-β-D-galactopyranose

Guidance literature:

Multi-step reaction with 4 steps

1: 55 percent / 3 Angstroem MS; NIS; TfOH / acetonitrile / -35 °C

2: 82 percent / H₂ / 10 percent Pd-C / acetic acid

3: 85 percent / DMAP / pyridine / 48 h / 20 °C

4: VF₃*Et₂O / toluene / 4 h / 20 °C

With dmap; vanadium(III) fluoride; N-iodo-succinimide; trifluorormethanesulfonic acid; 3 Angstroem MS; hydrogen; palladium on activated charcoal; In pyridine; acetic acid; toluene; acetonitrile; 1: coupled / 2: Hydrogenolysis / 3: Acylation / 4: Acetylation;

DOI:10.1080/07328300008544114

upstream raw materials:

butanoic acid anhydride

acetic anhydride

(4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Downstream raw materials:

2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosulonate)-(2->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside