(2R,5S,10aS,10bS)-2-Benzyloxycarbonylamino-5-benzyl-10b-hydroxy-3,6-dioxo-octahydro-8H-oxazolo(3,2-a)-pyrrolo(2,1-c)-pyrazin

Base Information

• Chemical Name: (2R,5S,10aS,10bS)-2-Benzyloxycarbonylamino-5-benzyl-10b-hydroxy-3,6-dioxo-octahydro-8H-oxazolo(3,2-a)-pyrrolo(2,1-c)-pyrazin
• CAS No.: 89762-59-4
• Molecular Formula: C₂₄H₂₅N₃O₆
• Molecular Weight: 451.479
• Mol file: 89762-59-4.mol

Synonyms:

Chemical Property of (2R,5S,10aS,10bS)-2-Benzyloxycarbonylamino-5-benzyl-10b-hydroxy-3,6-dioxo-octahydro-8H-oxazolo(3,2-a)-pyrrolo(2,1-c)-pyrazin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S,10aS,10bS)-2-Benzyloxycarbonylamino-5-benzyl-10b-hydroxy-3,6-dioxo-octahydro-8H-oxazolo(3,2-a)-pyrrolo(2,1-c)-pyrazin

There total 10 articles about (2R,5S,10aS,10bS)-2-Benzyloxycarbonylamino-5-benzyl-10b-hydroxy-3,6-dioxo-octahydro-8H-oxazolo(3,2-a)-pyrrolo(2,1-c)-pyrazin 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: 0.9%

Benzyloxycarbonyl-R,S-hydroxyglycyl-S-phenylalanyl-S-prolin-p-nitrophenylester (89762-57-2) → (2S,5S,10aS,10bS)-2-Benzyloxycarbonylamino-5-benzyl-10b-hydroxy-3,6-dioxo-octahydro-8H-oxazolo(3,2-a)-pyrrolo(2,1-c)-pyrazin (89762-58-3) + (2R,5S,10aS,10bS)-2-Benzyloxycarbonylamino-5-benzyl-10b-hydroxy-3,6-dioxo-octahydro-8H-oxazolo(3,2-a)-pyrrolo(2,1-c)-pyrazin (89762-59-4)

Guidance literature:

With potassium tartrate; In acetone; at 20 ℃; for 24h;

Reference yield: 0.5%

(2S,5S,10aS,10bS)-2-Benzyloxycarbonylamino-5-benzyl-10b-hydroxy-3,6-dioxo-octahydro-8H-oxazolo(3,2-a)-pyrrolo(2,1-c)-pyrazin (89762-58-3) → (2R,5S,10aS,10bS)-2-Benzyloxycarbonylamino-5-benzyl-10b-hydroxy-3,6-dioxo-octahydro-8H-oxazolo(3,2-a)-pyrrolo(2,1-c)-pyrazin (89762-59-4)

Guidance literature:

With acetic acid; In 1,4-dioxane; water; for 5h; Heating;

Reference yield:

L-phenylalanyl-L-proline tert-butyl ester (64830-74-6) → (2R,5S,10aS,10bS)-2-Benzyloxycarbonylamino-5-benzyl-10b-hydroxy-3,6-dioxo-octahydro-8H-oxazolo(3,2-a)-pyrrolo(2,1-c)-pyrazin (89762-59-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) HOBt, DCC / 1) ether, CH₂Cl₂, 0 deg C, 15 min, 2) 0 deg C, 45 min, 20 deg C, 12 h

2: 72.1 percent / CF₃COOH / 5 h / 20 °C

3: 41.4 percent / DCC / ethyl acetate / 3 h / 20 °C

4: 42.3 percent / lead tetraacetate / benzene / 0.25 h / Heating

5: 2.5 percent / 10percent potassium tartrate solution / acetone / 24 h / 20 °C

6: 0.5 percent / glacial acetic acid / dioxane; H₂O / 5 h / Heating

With lead(IV) acetate; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; potassium tartrate; In 1,4-dioxane; water; ethyl acetate; acetone; benzene;

upstream raw materials:

Benzyloxycarbonyl-R,S-hydroxyglycyl-S-phenylalanyl-S-prolin-p-nitrophenylester

(2S,5S,10aS,10bS)-2-Benzyloxycarbonylamino-5-benzyl-10b-hydroxy-3,6-dioxo-octahydro-8H-oxazolo(3,2-a)-pyrrolo(2,1-c)-pyrazin

L-phenylalanyl-L-proline tert-butyl ester

(1S)-methyl 2-[(S)-2-amino-3-phenylpropanoyl]cyclopentanecarboxylate