4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(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-(2,3-O-isopropylidene-α-L-rhamnopyranosyl)-β-D-galactopyranoside
• CAS No.: 403646-61-7
• Molecular Formula: C₃₇H₄₉NO₁₃
• Molecular Weight: 715.795
• Mol file: 403646-61-7.mol

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

Chemical Property of 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-isopropylidene-α-L-rhamnopyranosyl)-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-isopropylidene-α-L-rhamnopyranosyl)-β-D-galactopyranoside

There total 8 articles about 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(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: 80.0%

4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-α-L-rhamnopyranosyl)-β-D-galactopyranoside (403646-59-3) → 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-isopropylidene-α-L-rhamnopyranosyl)-β-D-galactopyranoside (403646-61-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 5h;

DOI:10.1021/jo0108818

Reference yield:

pivaloyl chloride (3282-30-2) → 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-isopropylidene-α-L-rhamnopyranosyl)-β-D-galactopyranoside (403646-61-7)

Guidance literature:

Multi-step reaction with 4 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

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:

S-phenyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-2-O-pivaloyl-1-thio-β-D-galactopyranoside (403646-42-4) → 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-isopropylidene-α-L-rhamnopyranosyl)-β-D-galactopyranoside (403646-61-7)

Guidance literature:

Multi-step reaction with 3 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

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

upstream raw materials:

4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-α-L-rhamnopyranosyl)-β-D-galactopyranoside

pivaloyl chloride

phenyl 1-thio-α-L-rhamnopyranose

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

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