(2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-((Z)-1-formyl-buta-1,3-dienyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-((Z)-1-formyl-buta-1,3-dienyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 121010-45-5
• Molecular Formula: C₂₉H₅₅NO₅Si₂
• Molecular Weight: 553.93

Synonyms:

Chemical Property of (2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-((Z)-1-formyl-buta-1,3-dienyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

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Useful:

Technology Process of (2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-((Z)-1-formyl-buta-1,3-dienyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 1 articles about (2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-((Z)-1-formyl-buta-1,3-dienyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 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:

(2S,3S,4S)-4-((E)-1-Benzenesulfinylmethyl-4-hydroxy-but-2-enyl)-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester → (2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-((Z)-1-formyl-buta-1,3-dienyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (121010-45-5) + (2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-((Z)-1-formyl-4-phenylsulfanyl-but-1-enyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/ja00222a044

Reference yield:

(2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-((Z)-1-formyl-buta-1,3-dienyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (121010-45-5) → acromelic acid B (86630-10-6)

Guidance literature:

Multi-step reaction with 6 steps

4: 1.) PDC / 1.) DMF, 40 degC, 16 h

5: 1.) mCPBA; 2.) TFAA / 1.) 16 h, r.t; 2.) DMF, 16 h, r.t.

6: 1.) KOH; 2.) TFA / 1.) MeOH, 16 h, r.t; 2.) 30 min, r.t.

With potassium hydroxide; dipyridinium dichromate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; trifluoroacetic anhydride;

DOI:10.1246/cl.1986.1399

Downstream raw materials:

acromelic acid B

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