(2R,3S,5S)-2-Benzoyloxymethyl-3-benzyloxy-5-vinyl-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2R,3S,5S)-2-Benzoyloxymethyl-3-benzyloxy-5-vinyl-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 146499-36-7
• Molecular Formula: C₂₉H₂₉NO₅
• Molecular Weight: 471.553
• Mol file: 146499-36-7.mol

Synonyms:(2R,3S,5S)-2-Benzoyloxymethyl-3-benzyloxy-5-vinyl-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property of (2R,3S,5S)-2-Benzoyloxymethyl-3-benzyloxy-5-vinyl-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,5S)-2-Benzoyloxymethyl-3-benzyloxy-5-vinyl-pyrrolidine-1-carboxylic acid benzyl ester

There total 8 articles about (2R,3S,5S)-2-Benzoyloxymethyl-3-benzyloxy-5-vinyl-pyrrolidine-1-carboxylic acid benzyl 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: 97.0%

benzoyl chloride (98-88-4) + (2R,3S,5S)-3-Benzyloxy-2-hydroxymethyl-5-vinyl-pyrrolidine-1-carboxylic acid benzyl ester (146499-28-7) → (2R,3S,5S)-2-Benzoyloxymethyl-3-benzyloxy-5-vinyl-pyrrolidine-1-carboxylic acid benzyl ester (146499-36-7)

Guidance literature:

With pyridine; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)74771-X

Reference yield:

Benzoic acid (Z)-(S)-5-methoxymethoxy-1-((R)-2-oxo-oxazolidin-4-yl)-pent-3-enyl ester (146499-33-4) → (2R,3S,5S)-2-Benzoyloxymethyl-3-benzyloxy-5-vinyl-pyrrolidine-1-carboxylic acid benzyl ester (146499-36-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 30 molpercent PdCl₂(MeCN)2 / tetrahydrofuran / Ambient temperature

2: 86 percent / 1N KOH / methanol / Ambient temperature

3: 96 percent / NaH

4: 100 percent / 1N KOH / methanol / Heating

5: 90 percent / NaHCO₃ / H₂O; CH₂Cl₂

6: 97 percent / pyridine / tetrahydrofuran

With pyridine; potassium hydroxide; sodium hydride; sodium hydrogencarbonate; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/S0040-4039(00)74771-X

Reference yield:

Benzoic acid (E)-(S)-5-methoxymethoxy-1-((R)-2-oxo-oxazolidin-4-yl)-pent-3-enyl ester (146499-34-5) → (2R,3S,5S)-2-Benzoyloxymethyl-3-benzyloxy-5-vinyl-pyrrolidine-1-carboxylic acid benzyl ester (146499-36-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 30 molpercent PdCl₂(MeCN)2 / tetrahydrofuran / Ambient temperature

2: 86 percent / 1N KOH / methanol / Ambient temperature

3: 96 percent / NaH

4: 100 percent / 1N KOH / methanol / Heating

5: 90 percent / NaHCO₃ / H₂O; CH₂Cl₂

6: 97 percent / pyridine / tetrahydrofuran

With pyridine; potassium hydroxide; sodium hydride; sodium hydrogencarbonate; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/S0040-4039(00)74771-X

upstream raw materials:

benzoyl chloride

(2R,3S,5S)-3-Benzyloxy-2-hydroxymethyl-5-vinyl-pyrrolidine-1-carboxylic acid benzyl ester

benzyl bromide

(5S,7S,7aR)-7-Hydroxy-5-vinyl-tetrahydro-pyrrolo[1,2-c]oxazol-3-one

Downstream raw materials:

(2S,4S,5R)-5-Benzoyloxymethyl-4-benzyloxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

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

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

(2R,3S,5S)-2-Benzoyloxymethyl-3-benzyloxy-5-formyl-pyrrolidine-1-carboxylic acid benzyl ester