phenyl 3-azido-4-O-benzoyl-2-O-benzyl-3,6-dideoxy-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 3-azido-4-O-benzoyl-2-O-benzyl-3,6-dideoxy-1-thio-β-D-glucopyranoside
• CAS No.: 868258-64-4
• Molecular Formula: C₂₆H₂₅N₃O₄S
• Molecular Weight: 475.568
• Mol file: 868258-64-4.mol

Synonyms:phenyl 3-azido-4-O-benzoyl-2-O-benzyl-3,6-dideoxy-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 3-azido-4-O-benzoyl-2-O-benzyl-3,6-dideoxy-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 3-azido-4-O-benzoyl-2-O-benzyl-3,6-dideoxy-1-thio-β-D-glucopyranoside

There total 6 articles about phenyl 3-azido-4-O-benzoyl-2-O-benzyl-3,6-dideoxy-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:

Benzoic acid (2R,3R,4R,5R,6S)-5-benzyloxy-2-methyl-6-phenylsulfanyl-4-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester → phenyl 3-azido-4-O-benzoyl-2-O-benzyl-3,6-dideoxy-1-thio-β-D-glucopyranoside (868258-64-4)

Guidance literature:

With sodium azide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm050368c

Reference yield:

phenyl 2-O-benzyl-1-thio-β-D-fucopyranoside (868258-60-0) → phenyl 3-azido-4-O-benzoyl-2-O-benzyl-3,6-dideoxy-1-thio-β-D-glucopyranoside (868258-64-4)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: CH₂Cl₂

3: 90 percent / MeONa / methanol / 2 h / 20 °C

4: 91 percent / DMAP; DIPEA / CH₂Cl₂ / -50 - -10 °C

5: CH₂Cl₂ / 1 h / 0 °C

6: 0.71 g / NaN₃ / CH₂Cl₂; dimethylformamide

With pyridine; dmap; sodium azide; sodium methylate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm050368c

Reference yield:

phenyl 2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside (868258-62-2) → phenyl 3-azido-4-O-benzoyl-2-O-benzyl-3,6-dideoxy-1-thio-β-D-glucopyranoside (868258-64-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / DMAP; DIPEA / CH₂Cl₂ / -50 - -10 °C

2: CH₂Cl₂ / 1 h / 0 °C

3: 0.71 g / NaN₃ / CH₂Cl₂; dimethylformamide

With dmap; sodium azide; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm050368c

upstream raw materials:

phenyl 2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside

phenyl 2-O-benzyl-1-thio-β-D-fucopyranoside

phenyl 3,4-di-O-acetyl-2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside

phenyl 4-O-benzoyl-2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside

Downstream raw materials:

6-O-(3-azido-2-O-benzyl-3,6-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine

6-O-(3-amino-3,6-dideoxy-α-D-glucopyranosyl)neamine

C₂₅H₃₁N₁₅O₇