(2R,3S)-(-)-2-(tert-butyldiphenylsilanyloxymethyl)-3-vinyltetrahydrofuran

Base Information

Chemical Name:(2R,3S)-(-)-2-(tert-butyldiphenylsilanyloxymethyl)-3-vinyltetrahydrofuran
CAS No.:765923-81-7
Molecular Formula:C₂₃H₃₀O₂Si
Molecular Weight:366.576
Hs Code.:

Synonyms:(2R,3S)-(-)-2-(tert-butyldiphenylsilanyloxymethyl)-3-vinyltetrahydrofuran

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Chemical Property of (2R,3S)-(-)-2-(tert-butyldiphenylsilanyloxymethyl)-3-vinyltetrahydrofuran

Chemical Property:

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Technology Process of (2R,3S)-(-)-2-(tert-butyldiphenylsilanyloxymethyl)-3-vinyltetrahydrofuran

There total 5 articles about (2R,3S)-(-)-2-(tert-butyldiphenylsilanyloxymethyl)-3-vinyltetrahydrofuran 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:

: (4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-vinyl-tetrahydro-furan-2-ol

: 765923-81-7
(2R,3S)-(-)-2-(tert-butyldiphenylsilanyloxymethyl)-3-vinyltetrahydrofuran

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -45 ℃; for 3h;
DOI:10.1016/j.tet.2004.06.060

Reference yield:

: 6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6
D-Glutamic acid

: 765923-81-7
(2R,3S)-(-)-2-(tert-butyldiphenylsilanyloxymethyl)-3-vinyltetrahydrofuran

Guidance literature:: Multi-step reaction with 8 steps

1: 55 percent / aq. NaNO₂; H₂SO₄ / 0 °C

2: 80 percent / NH₃*Me₂S / tetrahydrofuran / 0 °C

3: 85 percent / Et₃N; DMAP / CH₂Cl₂

4: LiHMDS / tetrahydrofuran / -78 °C

5: aq. H₂O₂ / CH₂Cl₂ / 0 °C

6: 80 percent / CuI; Me₂S / tetrahydrofuran / 2 h / -78 °C

7: DIBAL / CH₂Cl₂; toluene / 3 h / -78 °C

8: 809 mg / Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 3 h / -45 °C

With triethylsilane; dmap; copper(l) iodide; dimethylsulfide; ammonia, dimethyl sulfide; sulfuric acid; boron trifluoride diethyl etherate; dihydrogen peroxide; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; sodium nitrite; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/j.tet.2004.06.060

Reference yield:

: 52813-63-5
(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

: 765923-81-7
(2R,3S)-(-)-2-(tert-butyldiphenylsilanyloxymethyl)-3-vinyltetrahydrofuran

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / Et₃N; DMAP / CH₂Cl₂

2: LiHMDS / tetrahydrofuran / -78 °C

3: aq. H₂O₂ / CH₂Cl₂ / 0 °C

4: 80 percent / CuI; Me₂S / tetrahydrofuran / 2 h / -78 °C

5: DIBAL / CH₂Cl₂; toluene / 3 h / -78 °C

6: 809 mg / Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 3 h / -45 °C

With triethylsilane; dmap; copper(l) iodide; dimethylsulfide; boron trifluoride diethyl etherate; dihydrogen peroxide; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/j.tet.2004.06.060