phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1→2)-3,4,6-tri-Oacetyl-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1→2)-3,4,6-tri-Oacetyl-1-thio-α-D-mannopyranoside
• CAS No.: 239465-99-7
• Molecular Formula: C₃₂H₄₁NO₁₆S
• Molecular Weight: 727.741
• Mol file: 239465-99-7.mol

Synonyms:phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1→2)-3,4,6-tri-Oacetyl-1-thio-α-D-mannopyranoside

Chemical Property of phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1→2)-3,4,6-tri-Oacetyl-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1→2)-3,4,6-tri-Oacetyl-1-thio-α-D-mannopyranoside

There total 6 articles about phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1→2)-3,4,6-tri-Oacetyl-1-thio-α-D-mannopyranoside 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: 80.0%

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1→2)-4,6-O-benzylidene-3-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside + acetic anhydride (108-24-7) → phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1→2)-3,4,6-tri-Oacetyl-1-thio-α-D-mannopyranoside (239465-99-7)

Guidance literature:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1→2)-4,6-O-benzylidene-3-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

With acetic acid; zinc; at 40 ℃; for 24h;

acetic anhydride; With pyridine; at 20 ℃; for 12h;

DOI:10.1002/anie.201803536

Reference yield:

O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-D-mannopyranose (126354-04-9,136945-25-0) + thiophenol (108-98-5) → phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1→2)-3,4,6-tri-Oacetyl-1-thio-α-D-mannopyranoside (239465-99-7)

Guidance literature:

With tin(IV) chloride; In dichloromethane;

DOI:10.1016/S0040-4039(99)00930-2

Reference yield:

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-19-9) → phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1→2)-3,4,6-tri-Oacetyl-1-thio-α-D-mannopyranoside (239465-99-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: di(n-butyl)tin oxide / toluene / 3 h / Reflux

1.2: 70 °C

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -60 °C / Molecular sieve

3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

3.2: 24 h / 40 °C

3.3: 12 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; di(n-butyl)tin oxide; trifluoroacetic acid; In dichloromethane; toluene;

DOI:10.1002/anie.201803536

upstream raw materials:

O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-D-mannopyranose

thiophenol

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside

Downstream raw materials:

N-[2-(4,5-dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-hydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

N-[(2S,3R,4R,5S,6R)-2-((2R,3S,4S,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide