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

Base Information

Chemical Name:(1aS,8R,9aS)-dimethyl ester 8-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-oxo-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid
CAS No.:503305-90-6
Molecular Formula:C₃₂H₄₄N₂O₉Si
Molecular Weight:628.795
Hs Code.:

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

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

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

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MSDS Files:: SDS file from LookChem

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

There total 7 articles about (1aS,8R,9aS)-dimethyl ester 8-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-oxo-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: 96.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 503305-88-2
(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

: 503305-90-6
(1aS,8R,9aS)-dimethyl ester 8-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-oxo-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 - 0 ℃;
DOI:10.1002/anie.200290015 DOI:10.1021/jo035828t

Reference yield:

: 2746-25-0
p-Methoxybenzyl bromide

: 503305-90-6
(1aS,8R,9aS)-dimethyl ester 8-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-oxo-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: 86 percent / DIPEA / CH₂Cl₂ / 48 h

2.1: 80 percent / tris(dimethylamino)sulfur(trimethylsilyl)difluoride (TASF) / dimethylformamide; H₂O / 4 h / 20 °C

3.1: 75 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h

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

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

5.1: 70 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) / toluene / 48 h / 20 °C

6.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 0 °C

With 2,6-dimethylpyridine; tris(dimethylamino)sulfonium trimethylsilyldifluoride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo035828t

Reference yield:

: 477223-17-9
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

: 503305-90-6
(1aS,8R,9aS)-dimethyl ester 8-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-3-[(4-methoxyphenyl)methyl]-9-oxo-1H-azirino[2,3-c][1]benzazocine-1,5-dicarboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: 86 percent / DIPEA / CH₂Cl₂ / 48 h

2.1: 80 percent / tris(dimethylamino)sulfur(trimethylsilyl)difluoride (TASF) / dimethylformamide; H₂O / 4 h / 20 °C

3.1: 75 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h

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

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

5.1: 70 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) / toluene / 48 h / 20 °C

6.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 0 °C

With 2,6-dimethylpyridine; tris(dimethylamino)sulfonium trimethylsilyldifluoride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo035828t