(S)-1-[(S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2-(4-phenylacetoxy-benzyloxycarbonylamino)-propionyl]-pyrrolidine-2-carboxylic acid allyl ester

Base Information

• Chemical Name: (S)-1-[(S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2-(4-phenylacetoxy-benzyloxycarbonylamino)-propionyl]-pyrrolidine-2-carboxylic acid allyl ester
• CAS No.: 182485-45-6
• Molecular Formula: C₄₁H₄₉N₃O₁₆
• Molecular Weight: 839.851

Synonyms:(S)-1-[(S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2-(4-phenylacetoxy-benzyloxycarbonylamino)-propionyl]-pyrrolidine-2-carboxylic acid allyl ester

Chemical Property of (S)-1-[(S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2-(4-phenylacetoxy-benzyloxycarbonylamino)-propionyl]-pyrrolidine-2-carboxylic acid allyl ester

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Technology Process of (S)-1-[(S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2-(4-phenylacetoxy-benzyloxycarbonylamino)-propionyl]-pyrrolidine-2-carboxylic acid allyl ester

There total 3 articles about (S)-1-[(S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2-(4-phenylacetoxy-benzyloxycarbonylamino)-propionyl]-pyrrolidine-2-carboxylic acid allyl 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: 87.0%

prop-2-enyl pyrrolidine-2-carboxylate (88224-06-0) + N-(4-Phenylacetoxybenzyloxycarbonyl)-L-serine(O-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl) (182485-44-5) → (S)-1-[(S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2-(4-phenylacetoxy-benzyloxycarbonylamino)-propionyl]-pyrrolidine-2-carboxylic acid allyl ester (182485-45-6)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide;

Reference yield:

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline (10378-06-0,20757-53-3,35954-65-5,123483-77-2,134308-33-1) → (S)-1-[(S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2-(4-phenylacetoxy-benzyloxycarbonylamino)-propionyl]-pyrrolidine-2-carboxylic acid allyl ester (182485-45-6)

Guidance literature:

Multi-step reaction with 2 steps

2: 87 percent / EDC, HOBT

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide;

Reference yield:

(S)-3-Hydroxy-2-(4-phenylacetoxy-benzyloxycarbonylamino)-propionic acid → (S)-1-[(S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2-(4-phenylacetoxy-benzyloxycarbonylamino)-propionyl]-pyrrolidine-2-carboxylic acid allyl ester (182485-45-6)

Guidance literature:

Multi-step reaction with 2 steps

2: 87 percent / EDC, HOBT

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide;

upstream raw materials:

prop-2-enyl pyrrolidine-2-carboxylate

N-(4-Phenylacetoxybenzyloxycarbonyl)-L-serine(O-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline

Downstream raw materials:

(S)-1-[(S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2-(4-phenylacetoxy-benzyloxycarbonylamino)-propionyl]-pyrrolidine-2-carboxylic acid

C₅₉H₇₇N₅O₂₆

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