3-(2-{(R)-2-[(2R,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-propionaldehyde

Base Information

Chemical Name:3-(2-{(R)-2-[(2R,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-propionaldehyde
CAS No.:782479-12-3
Molecular Formula:C₃₆H₅₆O₆Si₂
Molecular Weight:641.008
Hs Code.:

3-(2-{(R)-2-[(2R,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-propionaldehyde

Synonyms:3-(2-{(R)-2-[(2R,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-propionaldehyde

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Chemical Property of 3-(2-{(R)-2-[(2R,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-propionaldehyde

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Technology Process of 3-(2-{(R)-2-[(2R,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-propionaldehyde

There total 4 articles about 3-(2-{(R)-2-[(2R,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-propionaldehyde 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: 95.0%

: 782479-35-0
2-But-3-enyl-2-{(R)-2-[(2R,3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolane

: 782479-12-3
3-(2-{(R)-2-[(2R,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-propionaldehyde

Guidance literature:: 2-But-3-enyl-2-{(R)-2-[(2R,3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolane; With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; tert-butyl alcohol; at 25 ℃; for 12h;

With sodium periodate; In tetrahydrofuran; water; tert-butyl alcohol; at 25 ℃; for 5h; pH=7;
DOI:10.1002/anie.200460696

Reference yield:

: 2-But-3-enyl-2-{(R)-2-[(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolane

: 782479-12-3
3-(2-{(R)-2-[(2R,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-propionaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / TBAF / tetrahydrofuran / 48 h / 25 °C

2: 90 percent / 4-DMAP; Et₃N / CH₂Cl₂ / 10 h / 25 °C

3: 95 percent / imidazole; 4-DMAP / CH₂Cl₂ / 0.5 h / 0 °C

4: N-methylmorpholine-N-oxide; OsO₄ / CH₂Cl₂; tetrahydrofuran; H₂O / 12 h / 25 °C

5: 29.16 g / NaIO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; various solvents / 3 h / 25 °C / pH 7

With 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane; various solvents; water; tert-butyl alcohol;
DOI:10.1021/ja054750q

Reference yield:

: 782479-33-8
(2R,3R,5S)-2-[(R)-2-(2-But-3-enyl-[1,3]dioxolan-2-yl)-propyl]-5-hydroxymethyl-tetrahydro-furan-3-ol

: 782479-12-3
3-(2-{(R)-2-[(2R,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-propionaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / 4-DMAP; Et₃N / CH₂Cl₂ / 10 h / 25 °C

2: 95 percent / imidazole; 4-DMAP / CH₂Cl₂ / 0.5 h / 0 °C

3: N-methylmorpholine-N-oxide; OsO₄ / CH₂Cl₂; tetrahydrofuran; H₂O / 12 h / 25 °C

4: 29.16 g / NaIO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; various solvents / 3 h / 25 °C / pH 7

With 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane; various solvents; water; tert-butyl alcohol;
DOI:10.1021/ja054750q