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
Hs Code.:

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

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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

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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

: 108-24-7
acetic anhydride

: 239465-99-7
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

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:

: 126354-04-9,136945-25-0
O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-D-mannopyranose

: 108-98-5
thiophenol

: 239465-99-7
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

Guidance literature:: With tin(IV) chloride; In dichloromethane;
DOI:10.1016/S0040-4039(99)00930-2

Reference yield:

: 159407-19-9
phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 239465-99-7
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

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