methyl N-(carbobenzyloxy)-4-hydroxy-5-(1',2',3',4'-tetrahydroxybutyl)prolinate

Base Information

• Chemical Name: methyl N-(carbobenzyloxy)-4-hydroxy-5-(1',2',3',4'-tetrahydroxybutyl)prolinate
• CAS No.: 145473-26-3
• Molecular Formula: C₁₈H₂₅NO₉
• Molecular Weight: 399.398

Synonyms:methyl N-(carbobenzyloxy)-4-hydroxy-5-(1',2',3',4'-tetrahydroxybutyl)prolinate

Chemical Property of methyl N-(carbobenzyloxy)-4-hydroxy-5-(1',2',3',4'-tetrahydroxybutyl)prolinate

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Technology Process of methyl N-(carbobenzyloxy)-4-hydroxy-5-(1',2',3',4'-tetrahydroxybutyl)prolinate

There total 2 articles about methyl N-(carbobenzyloxy)-4-hydroxy-5-(1',2',3',4'-tetrahydroxybutyl)prolinate 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:

benzyl chloroformate (501-53-1,94274-21-2) → methyl N-(carbobenzyloxy)-4-hydroxy-5-(1',2',3',4'-tetrahydroxybutyl)prolinate (145473-26-3)

Guidance literature:

Multi-step reaction with 2 steps

1: NaHCO₃ / H₂O / Ambient temperature

2: acetyl chloride / 3 h / Ambient temperature

With sodium hydrogencarbonate; acetyl chloride; In water;

DOI:10.1021/jo00053a051

Reference yield:

methanol (67-56-1) + (4S,5R)-4-Hydroxy-5-((1R,2S,3R)-1,2,3,4-tetrahydroxy-butyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester → methyl N-(carbobenzyloxy)-4-hydroxy-5-(1',2',3',4'-tetrahydroxybutyl)prolinate (145473-26-3) + methyl N-(carbobenzyloxy)-4-hydroxy-5-(1',2',3',4'-tetrahydroxybutyl)prolinate (145552-08-5)

Guidance literature:

With acetyl chloride; for 3h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo00053a051

Reference yield: 72.0%

methyl N-(carbobenzyloxy)-4-hydroxy-5-(1',2',3',4'-tetrahydroxybutyl)prolinate (145473-26-3) + p-toluenesulfonyl chloride (98-59-9) → (2R,4S,5R)-4-Hydroxy-5-[(1R,2S,3R)-1,2,3-trihydroxy-4-(toluene-4-sulfonyloxy)-butyl]-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (145473-27-4)

Guidance literature:

With pyridine; at 4 ℃;

DOI:10.1021/jo00053a051

upstream raw materials:

methanol

benzyl chloroformate

Downstream raw materials:

(2R,4S,5R)-4-Hydroxy-5-[(1R,2S,3R)-1,2,3-trihydroxy-4-(toluene-4-sulfonyloxy)-butyl]-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

(2R,4S,5S)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-2-carboxylic acid

(2R,4S,5S)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

(2R,4S,5R)-5-Formyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

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