benzyl (2S,9R,E)-1-(tert-butyldimethylsilyloxy)-9-hydroxy-6-oxotridec-4-en-2-ylcarbamate

Base Information

Chemical Name:benzyl (2S,9R,E)-1-(tert-butyldimethylsilyloxy)-9-hydroxy-6-oxotridec-4-en-2-ylcarbamate
CAS No.:1352964-75-0
Molecular Formula:C₂₇H₄₅NO₅Si
Molecular Weight:491.744
Hs Code.:

Synonyms:benzyl (2S,9R,E)-1-(tert-butyldimethylsilyloxy)-9-hydroxy-6-oxotridec-4-en-2-ylcarbamate

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Chemical Property of benzyl (2S,9R,E)-1-(tert-butyldimethylsilyloxy)-9-hydroxy-6-oxotridec-4-en-2-ylcarbamate

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Technology Process of benzyl (2S,9R,E)-1-(tert-butyldimethylsilyloxy)-9-hydroxy-6-oxotridec-4-en-2-ylcarbamate

There total 6 articles about benzyl (2S,9R,E)-1-(tert-butyldimethylsilyloxy)-9-hydroxy-6-oxotridec-4-en-2-ylcarbamate 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%

: 1352964-64-7
(S)-benzyl 1-(tert-butyldimethylsilyloxy)-4-oxobutan-2-ylcarbamate

: 1352964-82-9
(R)-dimethyl 5-hydroxy-2-oxononylphosphonate

: 1352964-75-0
benzyl (2S,9R,E)-1-(tert-butyldimethylsilyloxy)-9-hydroxy-6-oxotridec-4-en-2-ylcarbamate

Guidance literature:: (R)-dimethyl 5-hydroxy-2-oxononylphosphonate; With barium hydroxide octahydrate; In tetrahydrofuran; at 20 ℃; for 0.75h; Inert atmosphere;

(S)-benzyl 1-(tert-butyldimethylsilyloxy)-4-oxobutan-2-ylcarbamate; In tetrahydrofuran; water; at 20 ℃; for 4h;
DOI:10.1016/j.tet.2011.10.076

Reference yield:

: C₆H₁₃NO₂

: 1352964-75-0
benzyl (2S,9R,E)-1-(tert-butyldimethylsilyloxy)-9-hydroxy-6-oxotridec-4-en-2-ylcarbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 1 h / 0 - 20 °C

2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexanes / 1 h / -78 °C

3.2: 1 h

4.1: barium hydroxide octahydrate / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere

4.2: 4 h / 20 °C

With n-butyllithium; barium hydroxide octahydrate; palladium 10% on activated carbon; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; hexanes; ethyl acetate; acetonitrile; 1.1: Horner-Wadsworth-Emmons olefination / 4.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.tet.2011.10.076

Reference yield:

: C₁₀H₁₉NO₃

: 1352964-75-0
benzyl (2S,9R,E)-1-(tert-butyldimethylsilyloxy)-9-hydroxy-6-oxotridec-4-en-2-ylcarbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexanes / 1 h / -78 °C

2.2: 1 h

3.1: barium hydroxide octahydrate / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere

3.2: 4 h / 20 °C

With n-butyllithium; barium hydroxide octahydrate; palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; hexanes; ethyl acetate; 3.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.tet.2011.10.076