(2R,3R,4S,5R)-acetic acid 4-acetoxy-1-acetyl-3-(tert-butyl-dimethyl-ilanyloxy)-5-(dimethy-phenyl-silanyl)-piperidin-2-ylmethyl ester

Base Information

Chemical Name:(2R,3R,4S,5R)-acetic acid 4-acetoxy-1-acetyl-3-(tert-butyl-dimethyl-ilanyloxy)-5-(dimethy-phenyl-silanyl)-piperidin-2-ylmethyl ester
CAS No.:1310798-56-1
Molecular Formula:C₂₆H₄₃NO₆Si₂
Molecular Weight:521.802
Hs Code.:

Synonyms:(2R,3R,4S,5R)-acetic acid 4-acetoxy-1-acetyl-3-(tert-butyl-dimethyl-ilanyloxy)-5-(dimethy-phenyl-silanyl)-piperidin-2-ylmethyl ester

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Chemical Property of (2R,3R,4S,5R)-acetic acid 4-acetoxy-1-acetyl-3-(tert-butyl-dimethyl-ilanyloxy)-5-(dimethy-phenyl-silanyl)-piperidin-2-ylmethyl ester

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Technology Process of (2R,3R,4S,5R)-acetic acid 4-acetoxy-1-acetyl-3-(tert-butyl-dimethyl-ilanyloxy)-5-(dimethy-phenyl-silanyl)-piperidin-2-ylmethyl ester

There total 7 articles about (2R,3R,4S,5R)-acetic acid 4-acetoxy-1-acetyl-3-(tert-butyl-dimethyl-ilanyloxy)-5-(dimethy-phenyl-silanyl)-piperidin-2-ylmethyl 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: 78.0%

: 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

: 108-24-7
acetic anhydride

: 1310798-56-1
(2R,3R,4S,5R)-acetic acid 4-acetoxy-1-acetyl-3-(tert-butyl-dimethyl-ilanyloxy)-5-(dimethy-phenyl-silanyl)-piperidin-2-ylmethyl ester

Guidance literature:: (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; With lithium aluminium tetrahydride; In diethyl ether;

acetic anhydride; In diethyl ether;
DOI:10.1002/ejoc.201100102

Reference yield:

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

: 1310798-56-1
(2R,3R,4S,5R)-acetic acid 4-acetoxy-1-acetyl-3-(tert-butyl-dimethyl-ilanyloxy)-5-(dimethy-phenyl-silanyl)-piperidin-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 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

5: lithium aluminium tetrahydride / diethyl ether

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; 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; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Sharpless epoxidation;
DOI:10.1002/ejoc.201100102

Reference yield:

: C₂₂H₂₇NO₆SSi

: 1310798-56-1
(2R,3R,4S,5R)-acetic acid 4-acetoxy-1-acetyl-3-(tert-butyl-dimethyl-ilanyloxy)-5-(dimethy-phenyl-silanyl)-piperidin-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide

1.2: HPLC / Resolution of racemate

2.1: lithium aluminium tetrahydride / diethyl ether

With 1H-imidazole; lithium aluminium tetrahydride; In diethyl ether; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201100102