methyl 4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:methyl 4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside
CAS No.:208048-07-1
Molecular Formula:C₄₈H₅₁N₃O₉S
Molecular Weight:846.014
Hs Code.:

Synonyms:methyl 4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

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Chemical Property of methyl 4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

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Technology Process of methyl 4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

There total 8 articles about methyl 4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 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:

: 208048-06-0
Trifluoro-methanesulfonic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

: 208048-07-1
methyl 4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 70 ℃; for 4.5h; Yield given;
DOI:10.1039/a709293h

Reference yield:

: 100-39-0
benzyl bromide

: 208048-07-1
methyl 4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 55 percent / NaH, CuCl₂ / dimethylformamide / 1.) r.t., 2 h, 2.) r.t., 42 h

2: 88 percent / pyridine / 3 h / 0 °C

3: molecular sieves 4 Angstroem, Br₂ / CH₂Cl₂ / 0.3 h / 0 °C

4: 2,6-di-tert-butyl-4-methylpyridine, silver triflate / CH₂Cl₂; toluene / 1.) -40 deg C, 30 min, 2.) -40 to -50 deg C, 40 min

5: 96 percent / NaOMe / dioxane; methanol / 2.75 h / 40 °C

6: pyridine / CH₂Cl₂ / 11 h / 0 °C

7: NaN₃ / dimethylformamide / 4.5 h / 70 °C

With pyridine; sodium azide; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; bromine; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; copper dichloride; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1039/a709293h

Reference yield:

: methyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside

: 208048-07-1
methyl 4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 55 percent / NaH, CuCl₂ / dimethylformamide / 1.) r.t., 2 h, 2.) r.t., 42 h

2: 88 percent / pyridine / 3 h / 0 °C

3: molecular sieves 4 Angstroem, Br₂ / CH₂Cl₂ / 0.3 h / 0 °C

4: 2,6-di-tert-butyl-4-methylpyridine, silver triflate / CH₂Cl₂; toluene / 1.) -40 deg C, 30 min, 2.) -40 to -50 deg C, 40 min

5: 96 percent / NaOMe / dioxane; methanol / 2.75 h / 40 °C

6: pyridine / CH₂Cl₂ / 11 h / 0 °C

7: NaN₃ / dimethylformamide / 4.5 h / 70 °C

With pyridine; sodium azide; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; bromine; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; copper dichloride; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1039/a709293h