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

Base Information

• Chemical Name: (2R,3S,5S)-3-Benzyloxy-2-hydroxymethyl-5-vinyl-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 146499-28-7
• Molecular Formula: C₂₂H₂₅NO₄
• Molecular Weight: 367.445
• Mol file: 146499-28-7.mol

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

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

There total 7 articles about (2R,3S,5S)-3-Benzyloxy-2-hydroxymethyl-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: 90.0%

benzyl chloroformate (501-53-1,94274-21-2) + ((2R,3S,5S)-3-Benzyloxy-5-vinyl-pyrrolidin-2-yl)-methanol (146499-27-6) → (2R,3S,5S)-3-Benzyloxy-2-hydroxymethyl-5-vinyl-pyrrolidine-1-carboxylic acid benzyl ester (146499-28-7)

Guidance literature:

With sodium hydrogencarbonate; In 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)-3-Benzyloxy-2-hydroxymethyl-5-vinyl-pyrrolidine-1-carboxylic acid benzyl ester (146499-28-7)

Guidance literature:

Multi-step reaction with 5 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

With 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 (Z)-(S)-5-methoxymethoxy-1-((R)-2-oxo-oxazolidin-4-yl)-pent-3-enyl ester (146499-33-4) → (2R,3S,5S)-3-Benzyloxy-2-hydroxymethyl-5-vinyl-pyrrolidine-1-carboxylic acid benzyl ester (146499-28-7)

Guidance literature:

Multi-step reaction with 5 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

With 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:

benzyl chloroformate

((2R,3S,5S)-3-Benzyloxy-5-vinyl-pyrrolidin-2-yl)-methanol

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

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