phenyl 4,6-O-benzylidene-3-O-(3-naphthalen-1-yl-prop-2-ynyl)-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 4,6-O-benzylidene-3-O-(3-naphthalen-1-yl-prop-2-ynyl)-1-thio-α-D-mannopyranoside
• CAS No.: 915221-33-9
• Molecular Formula: C₃₂H₂₈O₅S
• Molecular Weight: 524.637
• Mol file: 915221-33-9.mol

Synonyms:phenyl 4,6-O-benzylidene-3-O-(3-naphthalen-1-yl-prop-2-ynyl)-1-thio-α-D-mannopyranoside

Chemical Property of phenyl 4,6-O-benzylidene-3-O-(3-naphthalen-1-yl-prop-2-ynyl)-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 4,6-O-benzylidene-3-O-(3-naphthalen-1-yl-prop-2-ynyl)-1-thio-α-D-mannopyranoside

There total 2 articles about phenyl 4,6-O-benzylidene-3-O-(3-naphthalen-1-yl-prop-2-ynyl)-1-thio-α-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: 93.0%

3-(α-Naphthyl)propargyl bromide (352035-98-4) + phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-19-9) → phenyl 4,6-O-benzylidene-3-O-(3-naphthalen-1-yl-prop-2-ynyl)-1-thio-α-D-mannopyranoside (915221-33-9)

Guidance literature:

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside; With di(n-butyl)tin oxide; In toluene; for 3h; Heating;

3-(α-Naphthyl)propargyl bromide; With cesium fluoride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/ol061938l

Reference yield:

3-(naphthalene-1-yl)prop-2-yn-1-ol (16176-22-0) → phenyl 4,6-O-benzylidene-3-O-(3-naphthalen-1-yl-prop-2-ynyl)-1-thio-α-D-mannopyranoside (915221-33-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 93 percent / triphenylphosphine; tetrabromocarbon / CH₂Cl₂ / 0.33 h / 0 °C

2.1: Bu₂SnO / toluene / 3 h / Heating

2.2: 93 percent / CsF / dimethylformamide / 20 °C

With carbon tetrabromide; di(n-butyl)tin oxide; triphenylphosphine; In dichloromethane; toluene;

DOI:10.1021/ol061938l

Reference yield: 97.0%

phenyl 4,6-O-benzylidene-3-O-(3-naphthalen-1-yl-prop-2-ynyl)-1-thio-α-D-mannopyranoside (915221-33-9) + benzyl bromide (100-39-0) → phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-(3-naphthalen-1-yl-prop-2-ynyl)-1-thio-α-D-mannopyranoside (915221-34-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

DOI:10.1021/ol061938l

upstream raw materials:

3-(α-Naphthyl)propargyl bromide

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

3-(naphthalene-1-yl)prop-2-yn-1-ol

Downstream raw materials:

phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-(3-naphthalen-1-yl-prop-2-ynyl)-1-thio-α-D-mannopyranoside

methyl 4-O-[4,6-O-benzylidene-2-O-benzyl-3-O-(3-naphthalen-1-yl-prop-2-ynyl)-β-D-mannopyranosyl]-(1->4)-2,3-O-isopropylidene-α-L-rhamanopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-[4,6-O-benzylidene-2-O-benzyl-3-O-(3-naphthalen-1-yl-prop-2-ynyl)-β-D-mannopyranosyl]-(1->4)-α-D-glucopyranoside