phenyl 7-azido-1,7-dideoxy-2,3,4,6-tetra-O-benzyl-1-thio-D-glycero-α-D-mannoheptopyranoside

Base Information

• Chemical Name: phenyl 7-azido-1,7-dideoxy-2,3,4,6-tetra-O-benzyl-1-thio-D-glycero-α-D-mannoheptopyranoside
• CAS No.: 1345664-79-0
• Molecular Formula: C₄₁H₄₁N₃O₅S
• Molecular Weight: 687.86

Synonyms:

Chemical Property of phenyl 7-azido-1,7-dideoxy-2,3,4,6-tetra-O-benzyl-1-thio-D-glycero-α-D-mannoheptopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 7-azido-1,7-dideoxy-2,3,4,6-tetra-O-benzyl-1-thio-D-glycero-α-D-mannoheptopyranoside

There total 9 articles about phenyl 7-azido-1,7-dideoxy-2,3,4,6-tetra-O-benzyl-1-thio-D-glycero-α-D-mannoheptopyranoside 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:

C42H44O8S2 → phenyl 7-azido-1,7-dideoxy-2,3,4,6-tetra-O-benzyl-1-thio-D-glycero-α-D-mannoheptopyranoside (1345664-79-0)

Guidance literature:

With sodium azide; tetrabutylammomium bromide; In N,N-dimethyl-formamide; at 90 ℃; for 24h; Inert atmosphere;

DOI:10.1002/chem.201100396

Reference yield:

phenyl 2,3,4-tri-O-benzyl-α-D-mannohexodialdopyranoside (1378357-82-4) → phenyl 7-azido-1,7-dideoxy-2,3,4,6-tetra-O-benzyl-1-thio-D-glycero-α-D-mannoheptopyranoside (1345664-79-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 20 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: potassium osmate(VI) dihydrate; water; potassium carbonate; potassium hexacyanoferrate(III) / toluene; tert-butyl alcohol / 96 h / 0 - 20 °C / Inert atmosphere

3.1: 1H-imidazole / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 17 h / 20 °C / Inert atmosphere

6.1: dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

7.1: sodium azide; tetrabutylammomium bromide / N,N-dimethyl-formamide / 24 h / 90 °C / Inert atmosphere

With 1H-imidazole; dmap; potassium osmate(VI) dihydrate; n-butyllithium; sodium azide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; water; sodium hydride; potassium carbonate; potassium hexacyanoferrate(III); In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; tert-butyl alcohol; 1.1: Wittig olefinization / 1.2: Wittig olefinization;

DOI:10.1002/chem.201100396

Reference yield:

phenyl 1-deoxy-2,3,4-tri-O-benzyl-1-thio-α-D-manno-hept-6-enopyranoside (1345664-73-4) → phenyl 7-azido-1,7-dideoxy-2,3,4,6-tetra-O-benzyl-1-thio-D-glycero-α-D-mannoheptopyranoside (1345664-79-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium osmate(VI) dihydrate; water; potassium carbonate; potassium hexacyanoferrate(III) / toluene; tert-butyl alcohol / 96 h / 0 - 20 °C / Inert atmosphere

2.1: 1H-imidazole / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / Inert atmosphere

3.2: 0 - 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 17 h / 20 °C / Inert atmosphere

5.1: dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

6.1: sodium azide; tetrabutylammomium bromide / N,N-dimethyl-formamide / 24 h / 90 °C / Inert atmosphere

With 1H-imidazole; dmap; potassium osmate(VI) dihydrate; sodium azide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; water; sodium hydride; potassium carbonate; potassium hexacyanoferrate(III); In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; tert-butyl alcohol;

DOI:10.1002/chem.201100396

upstream raw materials:

phenyl 1-deoxy-2,3,4,6-tetra-O-benzyl-1-thio-D-glycero-α-D-manno-heptopyranoside

phenyl 2,3,4-tri-O-benzyl-α-D-mannohexodialdopyranoside

phenyl 1-deoxy-2,3,4-tri-O-benzyl-1-thio-α-D-manno-hept-6-enopyranoside

phenyl 2,3,4-tri-O-benzyl-7-O-triisopropylsilyl-1-thio-D-glycero-α-D-mannoheptopyranoside

Downstream raw materials:

1-N-(phenyl 1,7-dideoxy-2,3,4,6-tetra-O-benzyl-1-thio-D-glycero-α-D-mannoheptopyranosid-7-yl)-4,5-dihydroxymethyl-1H-1,2,3-triazole

7-deoxy-7-(dibenzylphosphoramido)-2,3,4,6-tetra-O-benzyl-D-glycero-D-manno-heptopyranoside

thiophenyl 1,7-dideoxy-7-methanesulfonylamido-2,3,4,6-tetra-O-benzyl-D-glycero-α-D-manno-heptopyranoside

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