(5S,6S)-5-(2-methyl-2-butenoyloxy)-6-[(2S)-2-(tert-butyldiphenylsilanyloxy)propionyloxymethyl]-5,6-dihydropyran-2-one

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Chemical Name:(5S,6S)-5-(2-methyl-2-butenoyloxy)-6-[(2S)-2-(tert-butyldiphenylsilanyloxy)propionyloxymethyl]-5,6-dihydropyran-2-one
CAS No.:691371-35-4
Molecular Formula:C₃₀H₃₆O₇Si
Molecular Weight:536.697
Hs Code.:

Synonyms:(5S,6S)-5-(2-methyl-2-butenoyloxy)-6-[(2S)-2-(tert-butyldiphenylsilanyloxy)propionyloxymethyl]-5,6-dihydropyran-2-one

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Chemical Property of (5S,6S)-5-(2-methyl-2-butenoyloxy)-6-[(2S)-2-(tert-butyldiphenylsilanyloxy)propionyloxymethyl]-5,6-dihydropyran-2-one

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Technology Process of (5S,6S)-5-(2-methyl-2-butenoyloxy)-6-[(2S)-2-(tert-butyldiphenylsilanyloxy)propionyloxymethyl]-5,6-dihydropyran-2-one

There total 6 articles about (5S,6S)-5-(2-methyl-2-butenoyloxy)-6-[(2S)-2-(tert-butyldiphenylsilanyloxy)propionyloxymethyl]-5,6-dihydropyran-2-one 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: 89.0%

: 125941-75-5
(S)-2-[(1,1-dimethylethyl)diphenylsilyl]oxypropanoic acid

: 691371-34-3
(5S,6S)-5-(2-methyl-2-butenoyloxy)-6-(hydroxymethyl)-5,6-dihydropyran-2-one

: 691371-35-4
(5S,6S)-5-(2-methyl-2-butenoyloxy)-6-[(2S)-2-(tert-butyldiphenylsilanyloxy)propionyloxymethyl]-5,6-dihydropyran-2-one

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 6h;
DOI:10.1016/j.tetlet.2003.11.089

Reference yield:

: 691371-32-1
2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(2-furanyl)ethanone

: 691371-35-4
(5S,6S)-5-(2-methyl-2-butenoyloxy)-6-[(2S)-2-(tert-butyldiphenylsilanyloxy)propionyloxymethyl]-5,6-dihydropyran-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 84 percent / formic acid; triethylamine / (R)-Ru(η⁶-mesitylene)-(S,S)-TsDPEN Noyori catalyst / CH2Cl2 / 24 h / 20 °C

2.1: 92 percent / NBS; NaHCO₃; NaOAc / tetrahydrofuran; H₂O / 0 °C

3.1: Jones reagent / acetone / 0 °C

3.2: 83 percent / NaBH₄; CeCl₃ / methanol; CH₂Cl₂ / -78 °C

4.1: 85 percent / dicyclohexylcarbodiimide; dimethylaminopyridine / CH₂Cl₂ / 5 h / 20 °C

5.1: 87 percent / HF / acetonitrile / 10 h / 20 °C

6.1: 89 percent / dicyclohexylcarbodiimide; dimethylaminopyridine / CH₂Cl₂ / 6 h / 20 °C

With dmap; N-Bromosuccinimide; formic acid; jones reagent; hydrogen fluoride; sodium acetate; sodium hydrogencarbonate; triethylamine; dicyclohexyl-carbodiimide; (R)-Ru(η⁶-mesitylene)-(S,S)-TsDPEN; In tetrahydrofuran; dichloromethane; water; acetone; acetonitrile; 1.1: Noyori asymmetric transfer hydrogenation / 2.1: Achmatowicz rearrangement / 3.2: Luche reduction;
DOI:10.1016/j.tetlet.2003.11.089

Reference yield:

: 102732-44-5
ethyl (S)-2-(tert-butyldiphenylsilyloxy)propanoate

: 691371-35-4
(5S,6S)-5-(2-methyl-2-butenoyloxy)-6-[(2S)-2-(tert-butyldiphenylsilanyloxy)propionyloxymethyl]-5,6-dihydropyran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 82 percent / KOH / methanol / 20 °C

2: 89 percent / dicyclohexylcarbodiimide; dimethylaminopyridine / CH₂Cl₂ / 6 h / 20 °C

With dmap; potassium hydroxide; dicyclohexyl-carbodiimide; In methanol; dichloromethane;
DOI:10.1016/j.tetlet.2003.11.089