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

Base Information

• Chemical Name: methyl (R)-2-(N-(4-methoxybenzyl)acrylamido)-2-((benzyloxy)methyl)-3-oxybutanoate
• CAS No.: 704910-33-8
• Molecular Formula: C₂₄H₂₇NO₆
• Molecular Weight: 425.481
• Mol file: 704910-33-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about methyl (R)-2-(N-(4-methoxybenzyl)acrylamido)-2-((benzyloxy)methyl)-3-oxybutanoate 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: 82.0%

(R)-methyl 2-benzyloxymethyl-2-(4-methoxybenzylamino)-3-oxobutanoate (887776-07-0) + acryloyl chloride (814-68-6,25189-84-8) → methyl (R)-2-(N-(4-methoxybenzyl)acrylamido)-2-((benzyloxy)methyl)-3-oxybutanoate (704910-33-8)

Guidance literature:

With 2,6-di-tert-butyl-pyridine; In dichloromethane; at 23 ℃; for 12h;

DOI:10.1021/ol060464n

Reference yield: 10.0%

(R)-methyl 2-benzyloxymethyl-2-(4-methoxybenzylamino)-3-oxobutanoate (887776-07-0) + acryloyl chloride (814-68-6,25189-84-8) → (1R,4R,5R)-4-benzyloxymethyl-3-(4-methoxybenzyl)-5-methyl-7-oxo-6-oxa-3-aza-bicyclo[3.2.0]heptane-4-carboxylic acid methyl ester + (1S,4R,5S)-4-benzyloxymethyl-3-(4-methoxybenzyl)-5-methyl-7-oxo-6-oxa-3-aza-bicyclo[3.2.0]heptane-4-carboxylic acid methyl ester + methyl (R)-2-(N-(4-methoxybenzyl)acrylamido)-2-((benzyloxy)methyl)-3-oxybutanoate (704910-33-8)

Guidance literature:

With pyridine; In dichloromethane; at 23 ℃; for 12h;

DOI:10.1021/ol060464n

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → methyl (R)-2-(N-(4-methoxybenzyl)acrylamido)-2-((benzyloxy)methyl)-3-oxybutanoate (704910-33-8)

Guidance literature:

Multi-step reaction with 5 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

With 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; diethyl ether; dichloromethane; 5.1: Dess-Martin oxidation;

DOI:10.1021/ja048613p

upstream raw materials:

(R)-methyl 2-benzyloxymethyl-2-(4-methoxybenzylamino)-3-oxobutanoate

acryloyl chloride

Benzyloxymethyl chloride

L-threonine methyl ester

Downstream raw materials:

methyl (2R,3R)-1-(4-methoxybenzyl)-2-((benzyloxy)methyl)-3-hydroxy-3-methyl-4-methylene-5-oxopyrrolidine-2-carboxaldehyde

methyl (2R,3S)-1-(4-methoxybenzyl)-2-((benzyloxy)methyl)-3-hydroxy-3-methyl-4-methylene-5-oxopyrrolidine-2-carboxaldehyde

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