dibenzyl (S)-2-(tert-butyldimethylsilylamino)succinate

Base Information

• Chemical Name: dibenzyl (S)-2-(tert-butyldimethylsilylamino)succinate
• CAS No.: 130540-09-9
• Molecular Formula: C₂₄H₃₃NO₄Si
• Molecular Weight: 427.616
• Mol file: 130540-09-9.mol

Synonyms:dibenzyl (S)-2-(tert-butyldimethylsilylamino)succinate

Chemical Property of dibenzyl (S)-2-(tert-butyldimethylsilylamino)succinate

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

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Technology Process of dibenzyl (S)-2-(tert-butyldimethylsilylamino)succinate

There total 5 articles about dibenzyl (S)-2-(tert-butyldimethylsilylamino)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: 98.0%

N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide (77377-52-7) + (4S)-N-tert-butyldimethylsilylazetidin-2-one-4-carboxylic acid (82938-50-9,162856-35-1) → dibenzyl (S)-2-(tert-butyldimethylsilylamino)succinate (130540-09-9)

Guidance literature:

With tert-butyldimethylsilyl chloride; In acetonitrile; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)85592-7

Reference yield: 86.0%

dibenzyl L-aspartate (2791-79-9) + tert-butyldimethylsilyl chloride (18162-48-6) → dibenzyl (S)-2-(tert-butyldimethylsilylamino)succinate (130540-09-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 16h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201402737

Reference yield:

dibenzyl L-aspartate toluene-4-sulphonate (2886-33-1) → dibenzyl (S)-2-(tert-butyldimethylsilylamino)succinate (130540-09-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / water

2: triethylamine; dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere

With dmap; potassium carbonate; triethylamine; In dichloromethane; water;

DOI:10.1002/ejoc.201402737

upstream raw materials:

N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide

(4S)-N-tert-butyldimethylsilylazetidin-2-one-4-carboxylic acid

dibenzyl L-aspartate toluene-4-sulphonate

toluene-4-sulfonic acid

Downstream raw materials:

(4S)-N-tert-butyldimethylsilylazetidin-2-one-4-carboxylic acid

benzyl (S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate

Refernces

• 1、 Baldwin, Jack E.,Adlington, Robert M.,Gollins, David W.,Schofield, Christopher J.. "STEREOSPECIFIC SYNTHESIS OF DEALANYLALAHOPCIN". . p. 4733 - 4748. Retrieved 2007/10/02.