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

Base Information

• Chemical Name: phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-(3-naphthalen-1-yl-prop-2-ynyl)-1-thio-α-D-mannopyranoside
• CAS No.: 915221-34-0
• Molecular Formula: C₃₉H₃₄O₅S
• Molecular Weight: 614.762
• Mol file: 915221-34-0.mol

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

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

There total 3 articles about phenyl 4,6-O-benzylidene-2-O-benzyl-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: 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

Reference yield:

3-(naphthalene-1-yl)prop-2-yn-1-ol (16176-22-0) → 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:

Multi-step reaction with 3 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

3.1: 97 percent / sodium hydride / dimethylformamide / 0.5 h / 0 °C

With carbon tetrabromide; sodium hydride; di(n-butyl)tin oxide; triphenylphosphine; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol061938l

Reference yield:

3-(α-Naphthyl)propargyl bromide (352035-98-4) → 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:

Multi-step reaction with 2 steps

1.1: Bu₂SnO / toluene / 3 h / Heating

1.2: 93 percent / CsF / dimethylformamide / 20 °C

2.1: 97 percent / sodium hydride / dimethylformamide / 0.5 h / 0 °C

With sodium hydride; di(n-butyl)tin oxide; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol061938l

upstream raw materials:

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

benzyl bromide

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

3-(α-Naphthyl)propargyl bromide

Downstream raw materials:

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

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