benzyl (p-tolyl 5-azido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulpyranosid)onate

Base Information

• Chemical Name: benzyl (p-tolyl 5-azido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulpyranosid)onate
• CAS No.: 445022-61-7
• Molecular Formula: C₅₁H₅₁N₃O₇S
• Molecular Weight: 850.048
• Mol file: 445022-61-7.mol

Synonyms:benzyl (p-tolyl 5-azido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulpyranosid)onate

Chemical Property of benzyl (p-tolyl 5-azido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulpyranosid)onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (p-tolyl 5-azido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulpyranosid)onate

There total 5 articles about benzyl (p-tolyl 5-azido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulpyranosid)onate 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: 67.0%

benzyl bromide (100-39-0) + benzyl (p-tolyl 5-azido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulpyranosid)onate (445022-69-5) → benzyl (p-tolyl 5-azido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulpyranosid)onate (445022-61-7)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(02)00057-5

Reference yield:

(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(benzyloxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate (113757-76-9) → benzyl (p-tolyl 5-azido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulpyranosid)onate (445022-61-7)

Guidance literature:

Multi-step reaction with 5 steps

1: HCl; AcCl / 48 h / 20 °C

2: 84 percent / iPr₂EtN / CH₂Cl₂ / 20 °C

3: 81 percent / methanesulfonic acid / methanol / 24 h / 60 °C

4: 84 percent / TfN₃; K₂CO₃; CuSO₄*5H₂O / CH₂Cl₂; methanol; H₂O / 18 h

5: 67 percent / NaH; Bu₄NI / dimethylformamide

With hydrogenchloride; methanesulfonic acid; triflic azide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; copper(II) sulfate; N-ethyl-N,N-diisopropylamine; acetyl chloride; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(02)00057-5

Reference yield:

benzyl (5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulpyranosid)onate (113757-77-0) → benzyl (p-tolyl 5-azido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulpyranosid)onate (445022-61-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / iPr₂EtN / CH₂Cl₂ / 20 °C

2: 81 percent / methanesulfonic acid / methanol / 24 h / 60 °C

3: 84 percent / TfN₃; K₂CO₃; CuSO₄*5H₂O / CH₂Cl₂; methanol; H₂O / 18 h

4: 67 percent / NaH; Bu₄NI / dimethylformamide

With methanesulfonic acid; triflic azide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; copper(II) sulfate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(02)00057-5

upstream raw materials:

benzyl bromide

benzyl (p-tolyl 5-azido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulpyranosid)onate

(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(benzyloxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

benzyl (5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulpyranosid)onate