2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate
• CAS No.: 1610609-80-7
• Molecular Formula: C₄₅H₅₀Cl₃NO₁₀
• Molecular Weight: 871.252
• Mol file: 1610609-80-7.mol

Synonyms:2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate

Chemical Property of 2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate

There total 4 articles about 2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate 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:

C43H50O10 + trichloroacetonitrile (545-06-2) → 2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate (1610609-80-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1016/j.carres.2014.04.004

Reference yield:

4-methoxyphenyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside (129163-33-3) → 2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate (1610609-80-7)

Guidance literature:

Multi-step reaction with 3 steps

1: trimethylsilyl trifluoromethanesulfonate; N-iodo-succinimide / dichloromethane / 1.5 h / -15 °C / Inert atmosphere

2: ammonium cerium (IV) nitrate / acetonitrile / 1.5 h / 20 °C

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 0 °C

With N-iodo-succinimide; ammonium cerium (IV) nitrate; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile;

DOI:10.1016/j.carres.2014.04.004

Reference yield:

ethyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside (138343-55-2) → 2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate (1610609-80-7)

Guidance literature:

Multi-step reaction with 3 steps

1: trimethylsilyl trifluoromethanesulfonate; N-iodo-succinimide / dichloromethane / 1.5 h / -15 °C / Inert atmosphere

2: ammonium cerium (IV) nitrate / acetonitrile / 1.5 h / 20 °C

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 0 °C

With N-iodo-succinimide; ammonium cerium (IV) nitrate; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile;

DOI:10.1016/j.carres.2014.04.004

upstream raw materials:

trichloroacetonitrile

4-methoxyphenyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside

ethyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside

p-methoxyphenyl 2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside

Downstream raw materials:

phenyl 2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside