2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(4-methoxybenzyl)-β-D-mannopyranoside

Base Information

• Chemical Name: 2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(4-methoxybenzyl)-β-D-mannopyranoside
• CAS No.: 203056-90-0
• Molecular Formula: C₂₉H₃₀N₄O₈
• Molecular Weight: 562.579
• Mol file: 203056-90-0.mol

Synonyms:

Chemical Property of 2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(4-methoxybenzyl)-β-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(4-methoxybenzyl)-β-D-mannopyranoside

There total 1 articles about 2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(4-methoxybenzyl)-β-D-mannopyranoside 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:

p-Methoxybenzyl bromide (2746-25-0) + 2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranoside → 2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(4-methoxybenzyl)-β-D-mannopyranoside (203056-90-0)

Guidance literature:

With barium hydroxide octahydrate; 4 A molecular sieve; barium(II) oxide; Yield given. Multistep reaction; 1.) DMF, 30 min, 2.) DMF, room temperature, 12 h;

DOI:10.1021/jo970983r

Reference yield:

2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(4-methoxybenzyl)-β-D-mannopyranoside (203056-90-0) → 2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(1,4,6-tri-O-benzyl-β-D-fructofuranosyl)-β-D-mannopyranoside

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) molecular sieves 4A, 2.) 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, room temperature

2: dimethyl(methylthio)sulfonium trifluoromethanesulfonate, molecular sieves 4A / CH₂Cl₂ / 16 h / Ambient temperature; other reagents: methyl trifluoromethanesulfonate, iodonium collidine perchlorate, iodonium collidine triflate

With 4 A molecular sieve; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;

DOI:10.1021/jo970983r

Reference yield:

2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(4-methoxybenzyl)-β-D-mannopyranoside (203056-90-0) → α-N-succinimido-α-[2-(4-nitrophenyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(1,4,6-tri-O-benzyl-β-D-fructofuranosyl-3-O-yl)-β-D-mannopyranoside]-4-methoxytoluene

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) molecular sieves 4A, 2.) 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, room temperature

2: CH₂Cl₂ / 16 h / Ambient temperature

With 4 A molecular sieve; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;

DOI:10.1021/jo970983r

upstream raw materials:

p-Methoxybenzyl bromide