p-nitrophenyl 3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzoyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside

Base Information

Chemical Name:p-nitrophenyl 3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzoyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside
CAS No.:136963-27-4
Molecular Formula:C₃₉H₅₁N₅O₁₆Si
Molecular Weight:873.943
Hs Code.:

p-nitrophenyl 3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzoyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside

Synonyms:p-nitrophenyl 3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzoyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside

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Chemical Property of p-nitrophenyl 3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzoyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside

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Technology Process of p-nitrophenyl 3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzoyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside

There total 9 articles about p-nitrophenyl 3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzoyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-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: 97.0%

: 98-88-4
benzoyl chloride

: 136963-26-3
Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[(2S,3S,4R,5S,6R)-3-azido-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-4-yl ester

: 136963-27-4
p-nitrophenyl 3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzoyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside

Guidance literature:: With pyridine; at 0 ℃; for 2h;
DOI:10.1016/0008-6215(92)84161-K

Reference yield:

: 61169-00-4
p-nitrophenyl 4,6-O-benzylidene-β-D-glucopyranoside

: 136963-27-4
p-nitrophenyl 3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzoyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

2: 82 percent / dimethyl (methylthio)sulfoniumtriflate, 4 Angstroem molecular sieves, 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 2 h / Ambient temperature

3: 1) hydrazine hydrate, 2) pyridine / 1) EtOH, reflux, overnight

4: 75 percent / 70percent aq. AcOH / 1 h / 70 °C

5: pyridine / Ambient temperature; overnight

6: 97 percent / pyridine / 2 h / 0 °C

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; hydrazine hydrate; acetic acid; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane;
DOI:10.1016/0008-6215(92)84161-K

Reference yield:

: 99409-32-2
ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 136963-27-4
p-nitrophenyl 3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzoyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / dimethyl (methylthio)sulfoniumtriflate, 4 Angstroem molecular sieves, 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: 1) hydrazine hydrate, 2) pyridine / 1) EtOH, reflux, overnight

3: 75 percent / 70percent aq. AcOH / 1 h / 70 °C

4: pyridine / Ambient temperature; overnight

5: 97 percent / pyridine / 2 h / 0 °C

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; hydrazine hydrate; acetic acid; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane;
DOI:10.1016/0008-6215(92)84161-K