(3R,6R)-1,4-Dibenzyl-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-6-(pyridin-2-ylsulfanyl)-piperazine-2,5-dione

Base Information

• Chemical Name: (3R,6R)-1,4-Dibenzyl-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-6-(pyridin-2-ylsulfanyl)-piperazine-2,5-dione
• CAS No.: 95694-74-9
• Molecular Formula: C₃₉H₅₇N₃O₄SSi₂
• Molecular Weight: 720.136

Synonyms:(3R,6R)-1,4-Dibenzyl-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-6-(pyridin-2-ylsulfanyl)-piperazine-2,5-dione

Chemical Property of (3R,6R)-1,4-Dibenzyl-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-6-(pyridin-2-ylsulfanyl)-piperazine-2,5-dione

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Technology Process of (3R,6R)-1,4-Dibenzyl-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-6-(pyridin-2-ylsulfanyl)-piperazine-2,5-dione

There total 3 articles about (3R,6R)-1,4-Dibenzyl-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-6-(pyridin-2-ylsulfanyl)-piperazine-2,5-dione 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: 46.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 1,4-dibenzyl-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-(hydroxypropyl)>-2,5-piperazinedione (95782-30-2) → (3R,6R)-1,4-Dibenzyl-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-6-(pyridin-2-ylsulfanyl)-piperazine-2,5-dione (95694-74-9) + 1,4-dibenzyl-3-(2'-thiopyridyl)-6-<1''-<((tert-butyldimethylsilyl)oxy)methyl>-3''-(hydroxypropyl)>-2,5-piperazinedione (95782-33-5) + 1,4-dibenzyl-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-<((tert-butyldimethylsilyl)oxy)propyl>>-2,5-piperazinedione (95782-32-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1021/ja00297a035

Reference yield: 46.0%

tert-butyldimethylsilyl chloride (18162-48-6) + C36H60O29 (95784-48-8) → (3R,6R)-1,4-Dibenzyl-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-6-(pyridin-2-ylsulfanyl)-piperazine-2,5-dione (95694-74-9) + 1,4-dibenzyl-3-(2'-thiopyridyl)-6-<1''-<((tert-butyldimethylsilyl)oxy)methyl>-3''-(hydroxypropyl)>-2,5-piperazinedione (95782-33-5) + 1,4-dibenzyl-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-<((tert-butyldimethylsilyl)oxy)propyl>>-2,5-piperazinedione (95782-32-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1021/ja00297a035

Reference yield:

1,4-dimethyl-3-(2'-thiopyridyl)-6-(2''-δ-valerolactonyl)-2,5-piperazinedione (syn, minor diastereomer) (92216-23-4) → (3R,6R)-1,4-Dibenzyl-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-6-(pyridin-2-ylsulfanyl)-piperazine-2,5-dione (95694-74-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 47.3 percent / lithium aluminium hydride / tetrahydrofuran / 0.33 h / 0 °C

2: 19.1 percent / DMAP, triethylamine / CH₂Cl₂ / 24 h / Ambient temperature

With dmap; lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00297a035

upstream raw materials:

tert-butyldimethylsilyl chloride

1,4-dibenzyl-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-(hydroxypropyl)>-2,5-piperazinedione

C₃₆H₆₀O₂₉

1,4-dimethyl-3-(2'-thiopyridyl)-6-(2''-δ-valerolactonyl)-2,5-piperazinedione (syn, minor diastereomer)

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