(1aS,9aS)-dimethyl ester-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-[[diethyl(1-methylethyl)silyl]oxy]-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid

Base Information

• Chemical Name: (1aS,9aS)-dimethyl ester-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-[[diethyl(1-methylethyl)silyl]oxy]-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid
• CAS No.: 503305-94-0
• Molecular Formula: C₃₂H₄₆N₂O₈Si
• Molecular Weight: 614.811
• Mol file: 503305-94-0.mol

Synonyms:(1aS,9aS)-dimethyl ester-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-[[diethyl(1-methylethyl)silyl]oxy]-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid

Chemical Property of (1aS,9aS)-dimethyl ester-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-[[diethyl(1-methylethyl)silyl]oxy]-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1aS,9aS)-dimethyl ester-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-[[diethyl(1-methylethyl)silyl]oxy]-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid

There total 1 articles about (1aS,9aS)-dimethyl ester-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-[[diethyl(1-methylethyl)silyl]oxy]-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid 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: 86.0%

p-Methoxybenzyl bromide (2746-25-0) + 9-(diethyl-isopropyl-silanyloxy)-7-methoxymethoxy-1a,2,3,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cyclooctene-1,5-dicarboxylic acid dimethyl ester (477223-17-9) → (1aS,9aS)-dimethyl ester-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-[[diethyl(1-methylethyl)silyl]oxy]-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid (503305-94-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1002/anie.200290015

Reference yield: 80.0%

(1aS,9aS)-dimethyl ester-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-[[diethyl(1-methylethyl)silyl]oxy]-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid (503305-94-0) → (1aS,9aS)-dimethyl ester-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-hydroxy-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid (686722-20-3)

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In water; N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1021/jo035828t

Reference yield:

(1aS,9aS)-dimethyl ester-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-[[diethyl(1-methylethyl)silyl]oxy]-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid (503305-94-0) → (1aS,8R,9aS)-dimethyl ester 1a,2,3,8,9,9a-hexahydro-8-(hydroxymethyl)-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-oxo-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid (503305-88-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 80 percent / tris(dimethylamino)sulfur(trimethylsilyl)difluoride (TASF) / dimethylformamide; H₂O / 4 h / 20 °C

2.1: 75 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h

3.1: LDA / dimethylformamide / 0.25 h / -45 °C

3.2: dimethylformamide; tetrahydrofuran / 0.75 h / -45 °C

4.1: 70 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) / toluene / 48 h / 20 °C

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo035828t

upstream raw materials:

p-Methoxybenzyl bromide

9-(diethyl-isopropyl-silanyloxy)-7-methoxymethoxy-1a,2,3,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cyclooctene-1,5-dicarboxylic acid dimethyl ester

Downstream raw materials:

(1aS,9aS)-dimethyl ester-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-hydroxy-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid

(1aS,9aS)-dimethyl ester 1a,2,3,8,9,9a-hexahydro-4-(methoxymethoxy)-7-[(4-methoxyphenyl)methyl]-9-oxo-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid

(1aS,8S,9aS)-dimethyl ester 1a,2,3,8,9,9a-hexahydro-8-(hydroxymethyl)-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-oxo-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid

(1aS,8R,9aS)-dimethyl ester 1a,2,3,8,9,9a-hexahydro-8-(hydroxymethyl)-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-oxo-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid