(2S,3S)-dibenzyl 2-benzyl-2-hydroxy-3-(4-methylphenylsulfonamido)succinate

Base Information

• Chemical Name: (2S,3S)-dibenzyl 2-benzyl-2-hydroxy-3-(4-methylphenylsulfonamido)succinate
• CAS No.: 1365265-55-9
• Molecular Formula: C₃₂H₃₁NO₇S
• Molecular Weight: 573.667
• Mol file: 1365265-55-9.mol

Synonyms:(2S,3S)-dibenzyl 2-benzyl-2-hydroxy-3-(4-methylphenylsulfonamido)succinate

Chemical Property of (2S,3S)-dibenzyl 2-benzyl-2-hydroxy-3-(4-methylphenylsulfonamido)succinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-dibenzyl 2-benzyl-2-hydroxy-3-(4-methylphenylsulfonamido)succinate

There total 4 articles about (2S,3S)-dibenzyl 2-benzyl-2-hydroxy-3-(4-methylphenylsulfonamido)succinate 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:

(E)-dibenzyl 2-benzylfumarate (1365265-51-5) + chloroamine-T (127-65-1) → C25H24O6 (1365265-58-2) + (2R,3R)-dibenzyl 2-benzyl-2-hydroxy-3-(4-methylphenylsulfonamido)succinate (1365265-68-4) + (2S,3S)-dibenzyl 2-benzyl-2-hydroxy-3-(4-methylphenylsulfonamido)succinate (1365265-55-9)

Guidance literature:

With potassium osmate(VI) dihydrate; water; 1,4-bis(9-O-dihydroquinidine)phthalazine; In acetonitrile; at 20 ℃; for 48.5h; optical yield given as %ee; enantioselective reaction;

DOI:10.1016/j.tetasy.2012.01.004

Reference yield:

benzyl bromide (100-39-0) → (2S,3S)-dibenzyl 2-benzyl-2-hydroxy-3-(4-methylphenylsulfonamido)succinate (1365265-55-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

1.3: 20 °C / Inert atmosphere

2.1: phthalimide; di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 3 h / 20 °C

3.1: potassium osmate(VI) dihydrate; water; 1,4-bis(9-O-dihydroquinidine)phthalazine / acetonitrile / 48.5 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium osmate(VI) dihydrate; phthalimide; di-isopropyl azodicarboxylate; water; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; acetonitrile; 2.1: Mitsunobu dehydration / 3.1: Sharpless asymmetric aminohydroxylation;

DOI:10.1016/j.tetasy.2012.01.004

Reference yield:

dibenzyl (2S,3R)-2-benzyl-3-hydroxybutanedioate (172275-56-8) → (2S,3S)-dibenzyl 2-benzyl-2-hydroxy-3-(4-methylphenylsulfonamido)succinate (1365265-55-9)

Guidance literature:

Multi-step reaction with 2 steps

1: phthalimide; di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 3 h / 20 °C

2: potassium osmate(VI) dihydrate; water; 1,4-bis(9-O-dihydroquinidine)phthalazine / acetonitrile / 48.5 h / 20 °C

With potassium osmate(VI) dihydrate; phthalimide; di-isopropyl azodicarboxylate; water; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; In tetrahydrofuran; acetonitrile; 1: Mitsunobu dehydration / 2: Sharpless asymmetric aminohydroxylation;

DOI:10.1016/j.tetasy.2012.01.004

upstream raw materials:

(E)-dibenzyl 2-benzylfumarate

chloroamine-T

benzyl bromide

dibenzyl (2S)-2-hydroxybutanedioate