isopropyl (2S)-2-benzyloxy-5-methyl-4-[(-2-tetrahydropyranyloxy)methyl]-4-hexenoate

Base Information

Chemical Name:isopropyl (2S)-2-benzyloxy-5-methyl-4-[(-2-tetrahydropyranyloxy)methyl]-4-hexenoate
CAS No.:351386-46-4
Molecular Formula:C₂₃H₃₄O₅
Molecular Weight:390.52
Hs Code.:

Synonyms:isopropyl (2S)-2-benzyloxy-5-methyl-4-[(-2-tetrahydropyranyloxy)methyl]-4-hexenoate

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Chemical Property of isopropyl (2S)-2-benzyloxy-5-methyl-4-[(-2-tetrahydropyranyloxy)methyl]-4-hexenoate

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Technology Process of isopropyl (2S)-2-benzyloxy-5-methyl-4-[(-2-tetrahydropyranyloxy)methyl]-4-hexenoate

There total 2 articles about isopropyl (2S)-2-benzyloxy-5-methyl-4-[(-2-tetrahydropyranyloxy)methyl]-4-hexenoate 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%

: 351386-44-2
isopropyl (2S)-2-hydroxy-5-methyl-4-[(2-tetrahydropyranyloxy)methyl]-4-hexenoate

: 100-39-0
benzyl bromide

: 351386-46-4
isopropyl (2S)-2-benzyloxy-5-methyl-4-[(-2-tetrahydropyranyloxy)methyl]-4-hexenoate

Guidance literature:: With potassium tert-butylate; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; for 0.5h;
DOI:10.1039/b010101j

Reference yield:

: 113327-37-0,147512-94-5,147512-99-0
(2S)-isopropyl-2-<(tert-butyldimethylsilyl)oxy>-5-methyl-4-<(2-tetrahydropyran-2-yloxy)methyl>-4-hexenoate

: 351386-46-4
isopropyl (2S)-2-benzyloxy-5-methyl-4-[(-2-tetrahydropyranyloxy)methyl]-4-hexenoate

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

2: 89 percent / tBuOK; Bu₄NI / tetrahydrofuran / 0.5 h / 20 °C

With potassium tert-butylate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran;
DOI:10.1039/b010101j

Reference yield:

: 351386-46-4
isopropyl (2S)-2-benzyloxy-5-methyl-4-[(-2-tetrahydropyranyloxy)methyl]-4-hexenoate

: ethyl (2Z,4S)-4-benzyloxy-8-hydroxy-7,7-dimethyl-6-oxo-3-[(trimethylsiloxy)methyl]oct-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: hexamethyldisilazane; BuLi / hexane; tetrahydrofuran / 0.17 h / -70 °C

1.2: TMEDA / hexane; tetrahydrofuran / 0.67 h

2.1: tBuOK / tetrahydrofuran / 0.05 h / 20 °C

2.2: 51 percent / tetrahydrofuran / 0.33 h / 20 °C

3.1: 61 percent / Ni(acac)2 / diethyl ether / 2 h / 20 °C

4.1: 84 percent / pyridinium tosylate; EtOH / 24 h / 50 °C

5.1: D-(-)-DET; Ti(OiPr)4; tBuOOH / molecular sieves 4 Angstroem / CH₂Cl₂; toluene / 0.5 h / -40 °C

5.2: 31 mg / BF₃*Et₂O / CH₂Cl₂ / 0.17 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; bis(acetylacetonate)nickel(II); n-butyllithium; ethanol; diethyl (2S,3S)-tartrate; potassium tert-butylate; pyridinium p-toluenesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane; 4 A molecular sieve; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 5.1: Sharpless epoxidation;
DOI:10.1039/b010101j