(3S,4R,5S)-3,4,5-Trihydroxy-cyclohex-1-enecarboxylic acid 2-trimethylsilanyl-ethyl ester

Base Information

Chemical Name:(3S,4R,5S)-3,4,5-Trihydroxy-cyclohex-1-enecarboxylic acid 2-trimethylsilanyl-ethyl ester
CAS No.:131928-07-9
Molecular Formula:C₁₂H₂₂O₅Si
Molecular Weight:274.389
Hs Code.:

Synonyms:(3S,4R,5S)-3,4,5-Trihydroxy-cyclohex-1-enecarboxylic acid 2-trimethylsilanyl-ethyl ester

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Chemical Property of (3S,4R,5S)-3,4,5-Trihydroxy-cyclohex-1-enecarboxylic acid 2-trimethylsilanyl-ethyl ester

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Technology Process of (3S,4R,5S)-3,4,5-Trihydroxy-cyclohex-1-enecarboxylic acid 2-trimethylsilanyl-ethyl ester

There total 4 articles about (3S,4R,5S)-3,4,5-Trihydroxy-cyclohex-1-enecarboxylic acid 2-trimethylsilanyl-ethyl 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: 94.0%

: 131928-06-8
(1R,2R,3R,4R,5S)-2-Acetoxy-3,4,5-trihydroxy-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester

: 131928-07-9
(3S,4R,5S)-3,4,5-Trihydroxy-cyclohex-1-enecarboxylic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 4h; Ambient temperature;
DOI:10.1016/S0040-4039(00)98012-2

Reference yield:

: 131494-24-1
2-(Trimethylsilyl)ethyl acrylate

: 131928-07-9
(3S,4R,5S)-3,4,5-Trihydroxy-cyclohex-1-enecarboxylic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 77 percent / hydroquinone monomethyl ether / xylene / 40 h / Heating

2: 96 percent / OsO₄, N-methylmorpholine-N-oxide (NMO) / tetrahydrofuran; H₂O / 8 h

3: 81 percent / KBr, 15percent AcOOH, AcOH, AcONa / 18 h / Ambient temperature

4: 94 percent / DBU / tetrahydrofuran / 4 h / Ambient temperature

With peracetic acid; osmium(VIII) oxide; sodium acetate; acetic acid; 4-methylmorpholine N-oxide; 4-methoxy-phenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium bromide; In tetrahydrofuran; water; xylene;
DOI:10.1016/S0040-4039(00)98012-2

Reference yield:

: 131967-64-1
(1S,2S,3S,4R,5R)-2-Acetoxy-5-(dimethyl-phenyl-silanyl)-3,4-dihydroxy-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester

: 131928-07-9
(3S,4R,5S)-3,4,5-Trihydroxy-cyclohex-1-enecarboxylic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 81 percent / KBr, 15percent AcOOH, AcOH, AcONa / 18 h / Ambient temperature

2: 94 percent / DBU / tetrahydrofuran / 4 h / Ambient temperature

With peracetic acid; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium bromide; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)98012-2