(S)-3-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde

Base Information

Chemical Name:(S)-3-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde
CAS No.:392663-09-1
Molecular Formula:C₃₁H₄₈O₄Si₂
Molecular Weight:540.891
Hs Code.:

Synonyms:(S)-3-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde

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Chemical Property of (S)-3-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde

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Technology Process of (S)-3-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde

There total 9 articles about (S)-3-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-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: 99.0%

: 392663-54-6
(S)-3-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-propan-1-ol

: 392663-09-1
(S)-3-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 25 ℃; for 2h;
DOI:10.1002/1521-3773(20011105)40

Reference yield:

: 157240-43-2
(4R)-4,5-isopropylidenedioxy-1-(dimethoxyphosphoryl)-2-pentanone

: 392663-09-1
(S)-3-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde

Guidance literature:: Multi-step reaction with 9 steps

1.1: LiCl; N,N-diisopropylethylamine / acetonitrile / 2 h / 25 °C

1.2: 86 percent / acetonitrile / 15 h / 25 °C

2.1: 98 percent / LiI; LiAlH₄ / diethyl ether / -100 - 0 °C

3.1: 97 percent / AcOH / H₂O / 5 h / 40 °C

4.1: 70 percent / NaHCO₃; N-iodosuccinimide / tetrahydrofuran / 36 h / 0 °C

5.1: 99 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 10 h / 25 °C

6.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 99 percent / H₂; Raney-Ni catalyst / ethanol / 1 h / 25 °C

8.1: 88 percent / H₂ / Pd(OH)2/C / ethanol / 3 h / 25 °C

9.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 25 °C

With 2,6-dimethylpyridine; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; Raney-Ni catalyst; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium iodide; palladium dihydroxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1021/ja0547477

Reference yield:

: 392663-03-5
(E)-(2R,4S,7S)-8-Benzyloxy-7-methyl-oct-5-ene-1,2,4-triol

: 392663-09-1
(S)-3-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: 70 percent / NaHCO₃; N-iodosuccinimide / tetrahydrofuran / 36 h / 0 °C

2: 99 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 10 h / 25 °C

3: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

4: 99 percent / H₂; Raney-Ni catalyst / ethanol / 1 h / 25 °C

5: 88 percent / H₂ / Pd(OH)2/C / ethanol / 3 h / 25 °C

6: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 25 °C

With 2,6-dimethylpyridine; dmap; N-iodo-succinimide; Raney-Ni catalyst; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/ja0547477