3-(2-{(S)-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-{(S)-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.:881651-61-2
Molecular Formula:C₃₆H₅₆O₆Si₂
Molecular Weight:641.008
Hs Code.:

3-(2-{(S)-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-{(S)-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-{(S)-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-{(S)-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 17 articles about 3-(2-{(S)-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:

: 4-(2-{(S)-2-[(2R,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-butane-1,2-diol

: 881651-61-2
3-(2-{(S)-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:: With sodium periodate; In various solvents; water; tert-butyl alcohol; at 20 ℃; for 5h; pH=7;
DOI:10.1021/ja054750q

Reference yield:

: 881651-48-5
(E)-(2S,4R,7S)-8-Benzyloxy-7-methyl-oct-5-ene-1,2,4-triol

: 881651-61-2
3-(2-{(S)-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 14 steps

1.1: 70 percent / N-iodosuccinimide; NaHCO₃ / tetrahydrofuran / 36 h / 0 °C

2.1: 99 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 0 - 25 °C

3.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 99 percent / H₂ / Raney-Ni / ethanol / 1 h / 25 °C

5.1: 88 percent / H₂ / Pd(OH)2/C / ethanol / 3 h / 25 °C

6.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 25 °C

7.1: Mg / tetrahydrofuran / 2 h / 25 °C

7.2: tetrahydrofuran / 2 h / -78 - 0 °C

8.1: 40.9 g / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 - 25 °C

9.1: 98 percent / triethyl orthoformate; p-TsOH / 2.5 h / 55 °C

10.1: 96 percent / TBAF / tetrahydrofuran / 48 h / 25 °C

11.1: 97 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 16 h / 0 - 25 °C

12.1: 98 percent / imidazole; 4-DMAP / CH₂Cl₂ / 0.5 h / 0 °C

13.1: N-methylmorpholine-N-oxide; OsO₄ / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 12 h / 25 °C

14.1: 41.5 g / NaIO₄ / 2-methyl-propan-2-ol; H₂O; various solvents / 5 h / 20 °C / pH 7

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium periodate; N-iodo-succinimide; osmium(VIII) oxide; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; magnesium; 4-methylmorpholine N-oxide; triethylamine; orthoformic acid triethyl ester; palladium dihydroxide; nickel; In tetrahydrofuran; ethanol; dichloromethane; various solvents; water; tert-butyl alcohol;
DOI:10.1021/ja054750q

Reference yield:

: 881651-50-9
(2S,3R,5S)-2-((1S,2R)-3-Benzyloxy-1-iodo-2-methyl-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

: 881651-61-2
3-(2-{(S)-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 12 steps

1.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

2.1: 99 percent / H₂ / Raney-Ni / ethanol / 1 h / 25 °C

3.1: 88 percent / H₂ / Pd(OH)2/C / ethanol / 3 h / 25 °C

4.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 25 °C

5.1: Mg / tetrahydrofuran / 2 h / 25 °C

5.2: tetrahydrofuran / 2 h / -78 - 0 °C

6.1: 40.9 g / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 - 25 °C

7.1: 98 percent / triethyl orthoformate; p-TsOH / 2.5 h / 55 °C

8.1: 96 percent / TBAF / tetrahydrofuran / 48 h / 25 °C

9.1: 97 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 16 h / 0 - 25 °C

10.1: 98 percent / imidazole; 4-DMAP / CH₂Cl₂ / 0.5 h / 0 °C

11.1: N-methylmorpholine-N-oxide; OsO₄ / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 12 h / 25 °C

12.1: 41.5 g / NaIO₄ / 2-methyl-propan-2-ol; H₂O; various solvents / 5 h / 20 °C / pH 7

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; toluene-4-sulfonic acid; magnesium; 4-methylmorpholine N-oxide; triethylamine; orthoformic acid triethyl ester; palladium dihydroxide; nickel; In tetrahydrofuran; ethanol; dichloromethane; various solvents; water; tert-butyl alcohol;
DOI:10.1021/ja054750q