(1S,4S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-1-(dimethyl-phenyl-silanyl)-3-(toluene-4-sulfonyl)-7-oxa-3-aza-bicyclo[4.1.0]heptane-4-carboxylic acid methyl ester

Base Information

Chemical Name:(1S,4S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-1-(dimethyl-phenyl-silanyl)-3-(toluene-4-sulfonyl)-7-oxa-3-aza-bicyclo[4.1.0]heptane-4-carboxylic acid methyl ester
CAS No.:1310798-55-0
Molecular Formula:C₂₈H₄₁NO₆SSi₂
Molecular Weight:575.874
Hs Code.:

(1S,4S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-1-(dimethyl-phenyl-silanyl)-3-(toluene-4-sulfonyl)-7-oxa-3-aza-bicyclo[4.1.0]heptane-4-carboxylic acid methyl ester

Synonyms:(1S,4S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-1-(dimethyl-phenyl-silanyl)-3-(toluene-4-sulfonyl)-7-oxa-3-aza-bicyclo[4.1.0]heptane-4-carboxylic acid methyl ester

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Chemical Property of (1S,4S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-1-(dimethyl-phenyl-silanyl)-3-(toluene-4-sulfonyl)-7-oxa-3-aza-bicyclo[4.1.0]heptane-4-carboxylic acid methyl ester

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Technology Process of (1S,4S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-1-(dimethyl-phenyl-silanyl)-3-(toluene-4-sulfonyl)-7-oxa-3-aza-bicyclo[4.1.0]heptane-4-carboxylic acid methyl ester

There total 5 articles about (1S,4S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-1-(dimethyl-phenyl-silanyl)-3-(toluene-4-sulfonyl)-7-oxa-3-aza-bicyclo[4.1.0]heptane-4-carboxylic acid methyl 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: 96.0%

: 1310798-53-8
C₂₂H₂₇NO₆SSi

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1310798-55-0
(1S,4S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-1-(dimethyl-phenyl-silanyl)-3-(toluene-4-sulfonyl)-7-oxa-3-aza-bicyclo[4.1.0]heptane-4-carboxylic acid methyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201100102

Reference yield:

: [[2-(dimethylphenylsilanyl)-4-hydroxybut-2-enyl]-(toluene-4-sulfonyl)amino]acetic acid methyl ester

: 1310798-55-0
(1S,4S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-1-(dimethyl-phenyl-silanyl)-3-(toluene-4-sulfonyl)-7-oxa-3-aza-bicyclo[4.1.0]heptane-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate / octane; dichloromethane / 168 h / -23 °C / Inert atmosphere; Molecular sieve

2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / tetrahydrofuran

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran

4: 1H-imidazole / N,N-dimethyl-formamide

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; octane; dichloromethane; N,N-dimethyl-formamide; 1: Sharpless epoxidation;
DOI:10.1002/ejoc.201100102

Reference yield:

: 1310798-52-7
(2S,3S)-[[2-(dimethyl-phenyl-silanyl)-3-hydroxymethyl-oxiranylmethyl]-(toluene-4-sulfonyl)amino]-acetic acid methyl ester

: 1310798-55-0
(1S,4S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-1-(dimethyl-phenyl-silanyl)-3-(toluene-4-sulfonyl)-7-oxa-3-aza-bicyclo[4.1.0]heptane-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / tetrahydrofuran

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran

3: 1H-imidazole / N,N-dimethyl-formamide

With 1H-imidazole; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201100102