2-{N-Cbz-N,O-isopropylidene-L-Thr-[(Z)-1-amino-1-propenyl]}-5-methyloxazole-4-carbonyl-L-Ser-L-Val-OH

Base Information

• Chemical Name: 2-{N-Cbz-N,O-isopropylidene-L-Thr-[(Z)-1-amino-1-propenyl]}-5-methyloxazole-4-carbonyl-L-Ser-L-Val-OH
• CAS No.: 334832-19-8
• Molecular Formula: C₃₁H₄₁N₅O₁₀
• Molecular Weight: 643.694
• Mol file: 334832-19-8.mol

Synonyms:2-{N-Cbz-N,O-isopropylidene-L-Thr-[(Z)-1-amino-1-propenyl]}-5-methyloxazole-4-carbonyl-L-Ser-L-Val-OH

Chemical Property of 2-{N-Cbz-N,O-isopropylidene-L-Thr-[(Z)-1-amino-1-propenyl]}-5-methyloxazole-4-carbonyl-L-Ser-L-Val-OH

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{N-Cbz-N,O-isopropylidene-L-Thr-[(Z)-1-amino-1-propenyl]}-5-methyloxazole-4-carbonyl-L-Ser-L-Val-OH

There total 5 articles about 2-{N-Cbz-N,O-isopropylidene-L-Thr-[(Z)-1-amino-1-propenyl]}-5-methyloxazole-4-carbonyl-L-Ser-L-Val-OH 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:

2-{N-Cbz-N,O-isopropylidene-L-Thr-[(Z)-1-amino-1-propenyl]}-5-methyloxazole-4-carbonyl-L-Ser-L-Val-OMe (334832-18-7) → 2-{N-Cbz-N,O-isopropylidene-L-Thr-[(Z)-1-amino-1-propenyl]}-5-methyloxazole-4-carbonyl-L-Ser-L-Val-OH (334832-19-8)

Guidance literature:

With lithium hydroxide; In 1,4-dioxane; water; at 0 - 20 ℃; for 4h;

DOI:10.1246/cl.2001.102

Reference yield:

Cbz-Ser(TBS)-L-Val-OMe (334832-15-4) → 2-{N-Cbz-N,O-isopropylidene-L-Thr-[(Z)-1-amino-1-propenyl]}-5-methyloxazole-4-carbonyl-L-Ser-L-Val-OH (334832-19-8)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Pd-C / methanol / 3 h / 20 °C

2: BOP; (i-Pr)2NEt / 7 h / 0 - 20 °C

3: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

4: LiOH / H₂O; dioxane / 4 h / 0 - 20 °C

With lithium hydroxide; tetrabutyl ammonium fluoride; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; water;

DOI:10.1246/cl.2001.102

Reference yield:

Ser(TBS)-L-Val-OMe → 2-{N-Cbz-N,O-isopropylidene-L-Thr-[(Z)-1-amino-1-propenyl]}-5-methyloxazole-4-carbonyl-L-Ser-L-Val-OH (334832-19-8)

Guidance literature:

Multi-step reaction with 3 steps

1: BOP; (i-Pr)2NEt / 7 h / 0 - 20 °C

2: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

3: LiOH / H₂O; dioxane / 4 h / 0 - 20 °C

With lithium hydroxide; tetrabutyl ammonium fluoride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1246/cl.2001.102

upstream raw materials:

2-{N-Cbz-N,O-isopropylidene-L-Thr-[(Z)-1-amino-1-propenyl]}-5-methyloxazole-4-carbonyl-L-Ser-L-Val-OMe

Cbz-Ser(TBS)-L-Val-OMe

(4S,5R)-4-((Z)-1-{4-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-1-methoxycarbonyl-2-methyl-propylcarbamoyl)-ethylcarbamoyl]-5-methyl-oxazol-2-yl}-propenylcarbamoyl)-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester

Downstream raw materials:

C₆₄H₈₈N₈O₁₅Si₂

4-(1-{4-[1-(1-{1-[4-(2-hydroxy-1-methoxycarbonyl-ethylcarbamoyl)-5-methyl-oxazol-2-yl]-vinylcarbamoyl}-2-methyl-propylcarbamoyl)-vinylcarbamoyl]-5-methyl-oxazol-2-yl}-propenylcarbamoyl)-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester

C₅₈H₇₀N₈O₁₃Si

C₅₈H₇₂N₈O₁₄Si