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100157-54-8

100157-54-8

Identification

Synonyms:Z-D-aThr(t-Bu)-OMe

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Relevant articles and documentsAll total 2 Articles be found

1,2,4-OXADIAZOLE AND THIADIAZOLE COMPOUNDS AS IMMUNOMODULATORS

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Page/Page column 86, (2016/09/26)

The present invention relates to 1,2,4-oxadiazole compounds of formula (I) and their use to inhibit the programmed cell death (PD1) signaling pathway and/or for treatment of disorders by inhibiting an immunosuppressive signal induced by PD-1,PD-L1 or PD-L2.

Process route upstream and downstream products

Process route

methyl iodide
74-88-4

methyl iodide

N-Carbobenzoxy-O-tert.-butyl-L-threonin-methylester
52785-41-8,85353-76-0,100157-54-8

N-Carbobenzoxy-O-tert.-butyl-L-threonin-methylester

Conditions
Conditions Yield
With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 3h;
6.4 g
N-carbobenzyloxy-D-allo-threonine methyl ester
100157-53-7

N-carbobenzyloxy-D-allo-threonine methyl ester

Z-D-aThr(t-Bu)-OMe
100157-54-8

Z-D-aThr(t-Bu)-OMe

Conditions
Conditions Yield
With sulfuric acid; In dichloromethane; at 20 ℃; for 120h;
68%
Conditions
Conditions Yield
With sulfuric acid; In dichloromethane; at 20 ℃; for 120h;
Conditions
Conditions Yield
With sulfuric acid; In dichloromethane; at 20 ℃; for 120h;
benzyl chloroformate
501-53-1,94274-21-2

benzyl chloroformate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: triethylamine / CHCl3 / 12 h / 0 °C
2: conc. H2SO4 / CH2Cl2 / 120 h / 20 °C
With sulfuric acid; triethylamine; In dichloromethane; chloroform;
N-Carbobenzoxy-O-tert.-butyl-L-threonin-methylester
52785-41-8,85353-76-0,100157-54-8

N-Carbobenzoxy-O-tert.-butyl-L-threonin-methylester

Conditions
Conditions Yield
Z-Thr(tBu), Diazomethan;
Z-D-aThr(t-Bu)-OMe
100157-54-8

Z-D-aThr(t-Bu)-OMe

Z-D-aThr(t-Bu)-OH
100157-55-9

Z-D-aThr(t-Bu)-OH

Conditions
Conditions Yield
With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 4h;
85%
N-Carbobenzoxy-O-tert.-butyl-L-threonin-methylester
52785-41-8,85353-76-0,100157-54-8

N-Carbobenzoxy-O-tert.-butyl-L-threonin-methylester

C<sub>16</sub>H<sub>25</sub>N<sub>3</sub>O<sub>4</sub>

C16H25N3O4

Conditions
Conditions Yield
With methanol; hydrazine hydrate; at 20 ℃; for 12h;
5.5 g
Conditions
Conditions Yield
With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 4h;
Conditions
Conditions Yield
With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 4h;

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