4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-[4-O-(4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranosyl]-β-D-galactopyranoside

Base Information

Chemical Name:4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-[4-O-(4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranosyl]-β-D-galactopyranoside
CAS No.:403646-68-4
Molecular Formula:C₆₆H₇₉NO₂₀
Molecular Weight:1206.35
Hs Code.:

4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-[4-O-(4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranosyl]-β-D-galactopyranoside

Synonyms:4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-[4-O-(4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranosyl]-β-D-galactopyranoside

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Chemical Property of 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-[4-O-(4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranosyl]-β-D-galactopyranoside

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Technology Process of 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-[4-O-(4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranosyl]-β-D-galactopyranoside

There total 12 articles about 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-[4-O-(4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranosyl]-β-D-galactopyranoside 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: 71.0%

: 403646-50-4
S-phenyl 4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-1-thio-α-D-mannnopyranoside

: 403646-61-7
4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-isopropylidene-α-L-rhamnopyranosyl)-β-D-galactopyranoside

: 403646-68-4
4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-[4-O-(4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranosyl]-β-D-galactopyranoside

: 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-[4-O-(4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-α-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranosyl]-β-D-galactopyranoside

Guidance literature:: With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -60 - 0 ℃;
DOI:10.1021/jo0108818

Reference yield:

: 3282-30-2
pivaloyl chloride

: 403646-68-4
4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-[4-O-(4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranosyl]-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / Et₃N; DMAP / CH₂Cl₂ / 24 h / Heating

2: 80 percent / 1-(benzenesulfinyl)piperidine; 4 Angstroem molecular sieves; triflic anhydride / CH₂Cl₂ / -78 - 0 °C

3: 64 percent / 1-(benzenesulfinyl)piperidine; 2,4,6-tri-tert-butylpyrimidine; triflic anhydride / CH₂Cl₂ / -60 - 0 °C

4: 80 percent / Bu₄NF / tetrahydrofuran / 5 h / 0 - 20 °C

5: 71 percent / 1-(benzenesulfinyl)piperidine; 2,4,6-tri-tert-butylpyrimidine; triflic anhydride / CH₂Cl₂ / -60 - 0 °C

With dmap; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; triethylamine; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo0108818

Reference yield:

: 403646-42-4
S-phenyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-2-O-pivaloyl-1-thio-β-D-galactopyranoside

: 403646-68-4
4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-[4-O-(4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranosyl]-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 80 percent / 1-(benzenesulfinyl)piperidine; 4 Angstroem molecular sieves; triflic anhydride / CH₂Cl₂ / -78 - 0 °C

2: 64 percent / 1-(benzenesulfinyl)piperidine; 2,4,6-tri-tert-butylpyrimidine; triflic anhydride / CH₂Cl₂ / -60 - 0 °C

3: 80 percent / Bu₄NF / tetrahydrofuran / 5 h / 0 - 20 °C

4: 71 percent / 1-(benzenesulfinyl)piperidine; 2,4,6-tri-tert-butylpyrimidine; triflic anhydride / CH₂Cl₂ / -60 - 0 °C

With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo0108818