phenyl 2,3-di-O-benzyl-6-deoxy-4-O-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexapyranosyl)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2,3-di-O-benzyl-6-deoxy-4-O-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexapyranosyl)-1-thio-β-D-glucopyranoside
• CAS No.: 124477-14-1
• Molecular Formula: C₄₆H₅₀O₇S
• Molecular Weight: 746.965
• Mol file: 124477-14-1.mol

Synonyms:phenyl 2,3-di-O-benzyl-6-deoxy-4-O-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexapyranosyl)-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 2,3-di-O-benzyl-6-deoxy-4-O-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexapyranosyl)-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,3-di-O-benzyl-6-deoxy-4-O-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexapyranosyl)-1-thio-β-D-glucopyranoside

There total 8 articles about phenyl 2,3-di-O-benzyl-6-deoxy-4-O-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexapyranosyl)-1-thio-β-D-glucopyranoside 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: 80.0%

phenyl 2,3-di-O-benzyl-6-deoxy-4-O-(3,4-di-O-benzyl-6-deoxy-2-O-(methylthio)thiocarbonyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (125209-26-9) → phenyl 2,3-di-O-benzyl-6-deoxy-4-O-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexapyranosyl)-1-thio-β-D-glucopyranoside (124477-14-1)

Guidance literature:

With azobisisobutyronitrile; tri-n-butyl-tin hydride; In toluene; Heating;

DOI:10.1016/0008-6215(89)85044-X

Reference yield:

phenyl 4-O-(2-O-acetyl-3,4-di-O-benzyl-6-deoxy-β-D-glucopyranosyl)-2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside (125085-11-2) → phenyl 2,3-di-O-benzyl-6-deoxy-4-O-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexapyranosyl)-1-thio-β-D-glucopyranoside (124477-14-1)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1016/S0040-4039(01)80442-1

Reference yield:

1,2-di-O-acetyl-3,4-di-O-benzyl-6-deoxy-β-D-glucopyranose (125135-31-1) → phenyl 2,3-di-O-benzyl-6-deoxy-4-O-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexapyranosyl)-1-thio-β-D-glucopyranoside (124477-14-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate, / 1.) CH₂Cl₂, RT; 1 h, 2.) CH₂Cl₂, -20 deg C, 20 min,

2: 100 percent / Na, / methanol; dioxane / Ambient temperature

3: 1.) NaH, imidazole, / 1.) oil, THF, RT; 1 h, 2.) THF, oil, RT; 20 min,

4: 80 percent / tributyltin hydride, α,α'-azobisisobutyronitrile, / toluene / Heating

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; azobisisobutyronitrile; tri-n-butyl-tin hydride; sodium; sodium hydride; In 1,4-dioxane; methanol; toluene;

DOI:10.1016/0008-6215(89)85044-X

upstream raw materials:

phenyl 4-O-(2-O-acetyl-3,4-di-O-benzyl-6-deoxy-β-D-glucopyranosyl)-2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside

phenyl 2,3-di-O-benzyl-6-deoxy-4-O-(3,4-di-O-benzyl-6-deoxy-2-O-(methylthio)thiocarbonyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

phenyl 2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside

1,2-di-O-acetyl-3,4-di-O-benzyl-6-deoxy-β-D-glucopyranose

Downstream raw materials:

1,5-anhydro-3-O-benzyl-2,6-dideoxy-4-O-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-D-arabino-hex-1-enitol