phenyl 6-O-tosyloxy-1-thio-β-D-mannopyranoside

Base Information

• Chemical Name: phenyl 6-O-tosyloxy-1-thio-β-D-mannopyranoside
• CAS No.: 1432492-21-1
• Molecular Formula: C₁₉H₂₂O₇S₂
• Molecular Weight: 426.511
• Mol file: 1432492-21-1.mol

Synonyms:phenyl 6-O-tosyloxy-1-thio-β-D-mannopyranoside

Chemical Property of phenyl 6-O-tosyloxy-1-thio-β-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of phenyl 6-O-tosyloxy-1-thio-β-D-mannopyranoside

There total 1 articles about phenyl 6-O-tosyloxy-1-thio-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: 84.0%

phenyl-1-thio-β-D-mannopyranoside (77481-63-1) + p-toluenesulfonyl chloride (98-59-9) → phenyl 6-O-tosyloxy-1-thio-β-D-mannopyranoside (1432492-21-1)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 6h; regioselective reaction; Inert atmosphere;

DOI:10.1039/c3ob40615f

Reference yield: 72.0%

phenyl 6-O-tosyloxy-1-thio-β-D-mannopyranoside (1432492-21-1) → phenyl 6-deoxy-1-thio-β-D-mannopyranoside (1432492-22-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 80 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c3ob40615f

Reference yield:

phenyl 6-O-tosyloxy-1-thio-β-D-mannopyranoside (1432492-21-1) → N-(benzyloxycarbonyl)-O-(3-O-benzoyl-2,4-diazido-2,4,6-trideoxy-α-D-galactopyranosyl)-L-serine methylester

Guidance literature:

Multi-step reaction with 6 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 80 °C / Inert atmosphere

2: dimethyltin dichloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / Inert atmosphere

3: pyridine / dichloromethane / 2 h / -10 - 10 °C / Inert atmosphere

4: sodium azide / N,N-dimethyl-formamide / 8 h / 20 °C / Inert atmosphere

5: bromine / dichloromethane / 1 h / Inert atmosphere

6: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 6 h / Molecular sieve; Inert atmosphere

With pyridine; lithium aluminium tetrahydride; sodium azide; bromine; dimethyltin dichloride; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/c3ob40615f

upstream raw materials:

phenyl-1-thio-β-D-mannopyranoside

p-toluenesulfonyl chloride

Downstream raw materials:

3-O-benzoyl-2,4-diazido-2,4,6-trideoxy-α-D-galactopyranoside trichloroacetimidate

N-(benzyloxycarbonyl)-O-(3-O-acetyl-2,4-diazido-2,4,6-trideoxy-α-D-galactopyranosyl)-L-serine methylester

N-(benzyloxycarbonyl)-O-(2,4-diazido-2,4,6-trideoxy-α-D-galactopyranosyl)-L-serine methylester

phenyl 6-deoxy-1-thio-β-D-mannopyranoside