diethyl (4R,5S,6S,7R)-4-azido-7-benzoyloxy-5-(tert-butyldimethylsilanyloxy)-6-hydroxy-oct-2-enedioate

Base Information

• Chemical Name: diethyl (4R,5S,6S,7R)-4-azido-7-benzoyloxy-5-(tert-butyldimethylsilanyloxy)-6-hydroxy-oct-2-enedioate
• CAS No.: 444340-73-2
• Molecular Formula: C₂₅H₃₇N₃O₈Si
• Molecular Weight: 535.67
• Mol file: 444340-73-2.mol

Synonyms:diethyl (4R,5S,6S,7R)-4-azido-7-benzoyloxy-5-(tert-butyldimethylsilanyloxy)-6-hydroxy-oct-2-enedioate

Chemical Property of diethyl (4R,5S,6S,7R)-4-azido-7-benzoyloxy-5-(tert-butyldimethylsilanyloxy)-6-hydroxy-oct-2-enedioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl (4R,5S,6S,7R)-4-azido-7-benzoyloxy-5-(tert-butyldimethylsilanyloxy)-6-hydroxy-oct-2-enedioate

There total 1 articles about diethyl (4R,5S,6S,7R)-4-azido-7-benzoyloxy-5-(tert-butyldimethylsilanyloxy)-6-hydroxy-oct-2-enedioate 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: 77.0%

(E)-(4R,5S,6R,7R)-7-Benzoyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dihydroxy-oct-2-enedioic acid diethyl ester (178939-04-3) → diethyl (4R,5S,6S,7R)-4-azido-7-benzoyloxy-5-(tert-butyldimethylsilanyloxy)-6-hydroxy-oct-2-enedioate (444340-73-2)

Guidance literature:

With hydrogen azide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; benzene;

DOI:10.1016/S0040-4020(02)00015-7

Reference yield: 62.0%

diethyl (4R,5S,6S,7R)-4-azido-7-benzoyloxy-5-(tert-butyldimethylsilanyloxy)-6-hydroxy-oct-2-enedioate (444340-73-2) → (3R,4S,5S,6S)-3-benzoyloxy-5-(tert-butyldimethylsilanyloxy)-6-(2-ethoxycarbonylvinyl)-4-hydroxy-piperidin-2-one (444340-75-4)

Guidance literature:

With triphenylphosphine; In tetrahydrofuran; water; for 2h; Heating;

DOI:10.1016/S0040-4020(02)00015-7

Reference yield:

diethyl (4R,5S,6S,7R)-4-azido-7-benzoyloxy-5-(tert-butyldimethylsilanyloxy)-6-hydroxy-oct-2-enedioate (444340-73-2) → (E)-(4S,5S,6R,7R)-4-Amino-7-benzoyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-oct-2-enedioic acid diethyl ester

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 0.333333h; under 1034.3 Torr;

DOI:10.1016/S0040-4020(02)00015-7

upstream raw materials:

(E)-(4R,5S,6R,7R)-7-Benzoyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dihydroxy-oct-2-enedioic acid diethyl ester

Downstream raw materials:

(3R,4S,5S,6S)-3-benzoyloxy-5-(tert-butyldimethylsilanyloxy)-6-(2-ethoxycarbonylvinyl)-4-hydroxy-piperidin-2-one