(2R,4S,5R)-4,5-di(tert-butyldimethylsilyloxy)-2-(cyclopropylmethyl)-6-phenylhexanoic acid

Base Information

Chemical Name:(2R,4S,5R)-4,5-di(tert-butyldimethylsilyloxy)-2-(cyclopropylmethyl)-6-phenylhexanoic acid
CAS No.:220589-02-6
Molecular Formula:C₂₈H₅₀O₄Si₂
Molecular Weight:506.874
Hs Code.:

Synonyms:(2R,4S,5R)-4,5-di(tert-butyldimethylsilyloxy)-2-(cyclopropylmethyl)-6-phenylhexanoic acid

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Chemical Property of (2R,4S,5R)-4,5-di(tert-butyldimethylsilyloxy)-2-(cyclopropylmethyl)-6-phenylhexanoic acid

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Technology Process of (2R,4S,5R)-4,5-di(tert-butyldimethylsilyloxy)-2-(cyclopropylmethyl)-6-phenylhexanoic acid

There total 10 articles about (2R,4S,5R)-4,5-di(tert-butyldimethylsilyloxy)-2-(cyclopropylmethyl)-6-phenylhexanoic acid 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%

: 108-48-5
2,6-dimethylpyridine

: Cd

: 69739-34-0
t-butyldimethylsiyl triflate

: 7732-18-5
water

: 584-08-7
potassium carbonate

: 220589-02-6
(2R,4S,5R)-4,5-di(tert-butyldimethylsilyloxy)-2-(cyclopropylmethyl)-6-phenylhexanoic acid

Guidance literature:: With sodium hydrogencarbonate; citric acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

Reference yield:

: C₃₄H₆₄O₄Si₃

: 220589-02-6
(2R,4S,5R)-4,5-di(tert-butyldimethylsilyloxy)-2-(cyclopropylmethyl)-6-phenylhexanoic acid

Guidance literature:: With potassium carbonate; In tetrahydrofuran; methanol; water; at 20 ℃;
DOI:10.1016/S0968-0896(98)80011-4

Reference yield:

: 6052-66-0,112370-40-8,123877-73-6
1-phenyl-3-buten-2-ol

: 220589-02-6
(2R,4S,5R)-4,5-di(tert-butyldimethylsilyloxy)-2-(cyclopropylmethyl)-6-phenylhexanoic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: 1,5-hexadiene; SOBr₂ / 1,2-dichloro-ethane / 1.5 h / 0 °C

2.1: n-BuLi; i-Pr₂NH / hexane; tetrahydrofuran / 1 h / -78 °C

2.2: 56 percent / DMPU / hexane; tetrahydrofuran / 2.75 h / -78 - 0 °C

3.1: 92 percent / H₂O₂; LiOH*H₂O / tetrahydrofuran; H₂O / 19 h / 0 - 25 °C

4.1: 80 percent / MCPBA / CH₂Cl₂ / 15.25 h / 0 - 25 °C

5.1: 44 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

6.1: LiOH*H₂O / tetrahydrofuran; H₂O / 25 °C

6.2: 2,6-lutidine / CH₂Cl₂; dimethylformamide / 0 - 25 °C

7.1: 550 mg / K₂CO₃ / methanol; tetrahydrofuran; H₂O / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; sulfurous dibromide; n-butyllithium; 1,5-Hexadien; dihydrogen peroxide; potassium carbonate; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; 1.1: Substitution / 2.1: Metallation / 2.2: Alkylation / 3.1: Hydrolysis / 4.1: Oxidation / 5.1: silylation / 6.1: Hydrolysis / 6.2: silylation / 7.1: Hydrolysis;
DOI:10.1016/S0968-0896(98)80011-4