3-azido-4-O-benzoyl-1,3-dideoxy-2-O-(2-diazo-3-oxobutanoyl)-1-thio-1,6-anhydro-D-altropyranose

Base Information

• Chemical Name: 3-azido-4-O-benzoyl-1,3-dideoxy-2-O-(2-diazo-3-oxobutanoyl)-1-thio-1,6-anhydro-D-altropyranose
• CAS No.: 1412898-40-8
• Molecular Formula: C₁₇H₁₅N₅O₆S
• Molecular Weight: 417.402

Synonyms:3-azido-4-O-benzoyl-1,3-dideoxy-2-O-(2-diazo-3-oxobutanoyl)-1-thio-1,6-anhydro-D-altropyranose

Chemical Property of 3-azido-4-O-benzoyl-1,3-dideoxy-2-O-(2-diazo-3-oxobutanoyl)-1-thio-1,6-anhydro-D-altropyranose

Chemical Property:

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Technology Process of 3-azido-4-O-benzoyl-1,3-dideoxy-2-O-(2-diazo-3-oxobutanoyl)-1-thio-1,6-anhydro-D-altropyranose

There total 3 articles about 3-azido-4-O-benzoyl-1,3-dideoxy-2-O-(2-diazo-3-oxobutanoyl)-1-thio-1,6-anhydro-D-altropyranose 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: 85.0%

3-azido-4-O-benzoyl-1,3-dideoxy-2-O-(3-oxobutanoyl)-1-thio-1,6-anhydro-D-altropyranose (1412898-39-5) → 3-azido-4-O-benzoyl-1,3-dideoxy-2-O-(2-diazo-3-oxobutanoyl)-1-thio-1,6-anhydro-D-altropyranose (1412898-40-8)

Guidance literature:

With p-carboxybenzenesulfonyl azide; triethylamine; In acetonitrile; at 0 - 20 ℃; for 18h; Inert atmosphere;

DOI:10.1039/c2ob26308d

Reference yield:

2-O-acetyl-3-azido-4-O-benzoyl-1,3-dideoxy-1-thio-1,6-anhydro-D-altropyranose (1412898-35-1) → 3-azido-4-O-benzoyl-1,3-dideoxy-2-O-(2-diazo-3-oxobutanoyl)-1-thio-1,6-anhydro-D-altropyranose (1412898-40-8)

Guidance literature:

Multi-step reaction with 3 steps

1: guanidine nitrate; water / ethanol / 0.67 h / 20 °C / Inert atmosphere

2: 5,5-dimethyl-1,3-cyclohexadiene / 0.5 h / 150 °C / Inert atmosphere

3: p-carboxybenzenesulfonyl azide; triethylamine / acetonitrile / 18 h / 0 - 20 °C / Inert atmosphere

With p-carboxybenzenesulfonyl azide; water; guanidine nitrate; triethylamine; In 5,5-dimethyl-1,3-cyclohexadiene; ethanol; acetonitrile;

DOI:10.1039/c2ob26308d

Reference yield:

3-azido-4-O-benzoyl-1,3-dideoxy-1-thio-1,6-anhydro-D-altropyranose (1412898-36-2) → 3-azido-4-O-benzoyl-1,3-dideoxy-2-O-(2-diazo-3-oxobutanoyl)-1-thio-1,6-anhydro-D-altropyranose (1412898-40-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 5,5-dimethyl-1,3-cyclohexadiene / 0.5 h / 150 °C / Inert atmosphere

2: p-carboxybenzenesulfonyl azide; triethylamine / acetonitrile / 18 h / 0 - 20 °C / Inert atmosphere

With p-carboxybenzenesulfonyl azide; triethylamine; In 5,5-dimethyl-1,3-cyclohexadiene; acetonitrile;

DOI:10.1039/c2ob26308d

upstream raw materials:

2-O-acetyl-3-azido-4-O-benzoyl-1,3-dideoxy-1-thio-1,6-anhydro-D-altropyranose

3-azido-4-O-benzoyl-1,3-dideoxy-1-thio-1,6-anhydro-D-altropyranose

3-azido-4-O-benzoyl-1,3-dideoxy-2-O-(3-oxobutanoyl)-1-thio-1,6-anhydro-D-altropyranose

Downstream raw materials:

(1S,5S,6R,7S,8S,10S)-2-acetyl-6-azido-7-benzoyloxy-4,9-dioxa-1-thiatricyclo[6.2.1.0^5,10]undecan-1-ium-2-id-3-one

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