(2S,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

Base Information

Chemical Name:(2S,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol
CAS No.:207591-89-7
Molecular Formula:C₃₆H₄₀O₅Si
Molecular Weight:580.796
Hs Code.:

Synonyms:(2S,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

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Chemical Property of (2S,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

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Technology Process of (2S,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

There total 1 articles about (2S,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol 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: 78.0%

: 195141-43-6
(2S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furan-3-one

: 6921-34-2
benzylmagnesium chloride

: 207591-89-7
(2S,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

Guidance literature:: In tetrahydrofuran; diethyl ether; at 5 ℃; for 0.5h;
DOI:10.1271/bbb.62.521

Reference yield: 88.0%

: 207591-89-7
(2S,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

: 207591-90-0
(2S,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-hydroxymethyl-tetrahydro-furan-3-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1271/bbb.62.521

Reference yield:

: 207591-89-7
(2S,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

: (3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-3-hydroxy-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent / n-Bu₄NF / tetrahydrofuran / 0.5 h / 0 °C

2: 74 percent / PPh₃, I₂, imidazole / toluene / 1 h / Heating

3: 95 percent / Zn / ethanol / 0.5 h / Heating

4: 89 percent / DMAP / 1 h / Ambient temperature

5: 71 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

6: 1.) OsO₄, NMO, 2. ) NaIO₄ / 1.) acetone, t-BuOH, H₂O, room temperature, 24 h, 2.) EtOAc, H₂O, room temperature, 2 h

7: 88 percent / K₂CO₃ / methanol / 0.5 h / Ambient temperature

8: 51 percent / Ag₂CO₃-celite / toluene / 1 h / Heating

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; iodine; potassium carbonate; triphenylphosphine; silver carbonate; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene;
DOI:10.1271/bbb.62.521