D-Proline, 3-hydroxy-1-[(4-methoxyphenyl)methyl]-3-methyl-4-methylene-5-oxo-2-[( phenylmethoxy)methyl]-, methyl ester, (3S)-

Base Information

• Chemical Name: D-Proline, 3-hydroxy-1-[(4-methoxyphenyl)methyl]-3-methyl-4-methylene-5-oxo-2-[( phenylmethoxy)methyl]-, methyl ester, (3S)-
• CAS No.: 704910-34-9
• Molecular Formula: C24H27NO6
• Molecular Weight: 425.481
• Mol file: 704910-34-9.mol

Synonyms:

Chemical Property of D-Proline, 3-hydroxy-1-[(4-methoxyphenyl)methyl]-3-methyl-4-methylene-5-oxo-2-[( phenylmethoxy)methyl]-, methyl ester, (3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of D-Proline, 3-hydroxy-1-[(4-methoxyphenyl)methyl]-3-methyl-4-methylene-5-oxo-2-[( phenylmethoxy)methyl]-, methyl ester, (3S)-

There total 16 articles about D-Proline, 3-hydroxy-1-[(4-methoxyphenyl)methyl]-3-methyl-4-methylene-5-oxo-2-[( phenylmethoxy)methyl]-, methyl ester, (3S)- 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:

methyl (R)-2-(N-(4-methoxybenzyl)acrylamido)-2-((benzyloxy)methyl)-3-oxybutanoate (704910-33-8) → methyl (2R,3R)-1-(4-methoxybenzyl)-2-((benzyloxy)methyl)-3-hydroxy-3-methyl-4-methylene-5-oxopyrrolidine-2-carboxaldehyde (704910-35-0) + methyl (2R,3S)-1-(4-methoxybenzyl)-2-((benzyloxy)methyl)-3-hydroxy-3-methyl-4-methylene-5-oxopyrrolidine-2-carboxaldehyde (704910-34-9)

Guidance literature:

With Quinuclidine; In 1,2-dimethoxyethane; at 0 ℃; for 168h;

DOI:10.1021/ja048613p

Reference yield:

(2R,3S)-2-Benzyloxymethyl-3-hydroxy-4-iodomethyl-1-(4-methoxy-benzyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester (1027961-34-7) → methyl (2R,3S)-1-(4-methoxybenzyl)-2-((benzyloxy)methyl)-3-hydroxy-3-methyl-4-methylene-5-oxopyrrolidine-2-carboxaldehyde (704910-34-9)

Guidance literature:

With triethylamine; In dichloromethane; at 23 ℃; for 0.5h;

DOI:10.1021/ol0508734

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → methyl (2R,3S)-1-(4-methoxybenzyl)-2-((benzyloxy)methyl)-3-hydroxy-3-methyl-4-methylene-5-oxopyrrolidine-2-carboxaldehyde (704910-34-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: LDA; HMPA / tetrahydrofuran / 1 h / -78 °C

1.2: 69 percent / tetrahydrofuran / 4 h / -78 °C

2.1: 90 percent / AcOH; NaCNBH₃ / 12 h / 40 °C

3.1: Et₃N / diethyl ether / 12 h / 23 °C

4.1: 28.3 g / diisopropylethylamine / CH₂Cl₂ / 1 h / 0 °C

5.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 23 °C

6.1: quinuclidine / 1,2-dimethoxy-ethane / 168 h / 0 °C

With Quinuclidine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium cyanoborohydride; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; 5.1: Dess-Martin oxidation / 6.1: Baylis-Hillman reaction;

DOI:10.1021/ja048613p

upstream raw materials:

methyl (R)-2-(N-(4-methoxybenzyl)acrylamido)-2-((benzyloxy)methyl)-3-oxybutanoate

(2R,3S)-2-Benzyloxymethyl-3-hydroxy-4-iodomethyl-1-(4-methoxy-benzyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

2-benzyloxymethyl-3-hydroxy-1-(4-methoxy-benzyl)-3-methyl-4-methylaminomethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

2-benzyloxymethyl-1-(4-methoxy-benzyl)-3-methyl-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester

Downstream raw materials:

(2R,3S)-2-Benzyloxymethyl-3-(bromomethyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyl)-3-methyl-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

(2R,3S)-2-Benzyloxymethyl-1-(4-methoxy-benzyl)-3-methyl-4-methylene-5-oxo-3-triethylsilanyloxy-pyrrolidine-2-carboxylic acid methyl ester

(2S,3S,4R)-2-Formyl-1-(4-methoxy-benzyl)-3,4-dimethyl-5-oxo-3-triethylsilanyloxy-pyrrolidine-2-carboxylic acid methyl ester

(3R,3aS,7aR)-3-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester