5'-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-p-toluoyl-N-benzyloxycarbonyl-isofagomine

Base Information

Chemical Name:5'-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-p-toluoyl-N-benzyloxycarbonyl-isofagomine
CAS No.:1593576-30-7
Molecular Formula:C₅₆H₅₇NO₁₁
Molecular Weight:920.069
Hs Code.:

Synonyms:5'-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-p-toluoyl-N-benzyloxycarbonyl-isofagomine

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Chemical Property of 5'-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-p-toluoyl-N-benzyloxycarbonyl-isofagomine

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Technology Process of 5'-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-p-toluoyl-N-benzyloxycarbonyl-isofagomine

There total 4 articles about 5'-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-p-toluoyl-N-benzyloxycarbonyl-isofagomine 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: 60.0%

: 4-methylphenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 1593576-28-3
5'-O-benzyl-3-O-p-toluoyl-N-benzyloxycarbonyl-isofagomine

: 1593576-30-7
5'-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-p-toluoyl-N-benzyloxycarbonyl-isofagomine

Guidance literature:: 4-methylphenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside; With 2,4,6-tri-tertbutylpyridine; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; In dichloromethane; at -65 ℃; for 0.166667h; Inert atmosphere;

5'-O-benzyl-3-O-p-toluoyl-N-benzyloxycarbonyl-isofagomine; In dichloromethane; at -65 - -40 ℃; for 1.5h; Inert atmosphere;
DOI:10.1002/anie.201308334

Reference yield:

: 1593576-27-2
4,5'-O-benzylidene-3-O-p-toluoyl-N-benzyloxycarbonyl-isofagomine

: 1593576-30-7
5'-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-p-toluoyl-N-benzyloxycarbonyl-isofagomine

Guidance literature:: Multi-step reaction with 2 steps

1.1: trifluoroacetic acid; triethylsilane / dichloromethane / 5.5 h / Molecular sieve; Inert atmosphere

2.1: trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 2,4,6-tri-tertbutylpyridine / dichloromethane / 0.17 h / -65 °C / Inert atmosphere

2.2: 1.5 h / -65 - -40 °C / Inert atmosphere

With triethylsilane; 2,4,6-tri-tertbutylpyridine; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; trifluoroacetic acid; In dichloromethane;
DOI:10.1002/anie.201308334

Reference yield:

: 874-60-2
4-methyl-benzoyl chloride

: 1593576-30-7
5'-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-p-toluoyl-N-benzyloxycarbonyl-isofagomine

Guidance literature:: Multi-step reaction with 3 steps

1.1: dmap; pyridine / dichloromethane / 3 h / Inert atmosphere

2.1: trifluoroacetic acid; triethylsilane / dichloromethane / 5.5 h / Molecular sieve; Inert atmosphere

3.1: trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 2,4,6-tri-tertbutylpyridine / dichloromethane / 0.17 h / -65 °C / Inert atmosphere

3.2: 1.5 h / -65 - -40 °C / Inert atmosphere

With pyridine; triethylsilane; dmap; 2,4,6-tri-tertbutylpyridine; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; trifluoroacetic acid; In dichloromethane;
DOI:10.1002/anie.201308334