(4R,5S)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Base Information

Chemical Name:(4R,5S)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde
CAS No.:308140-77-4
Molecular Formula:C₂₄H₃₁N₃O₄Si
Molecular Weight:453.613
Hs Code.:

Synonyms:(4R,5S)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

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Chemical Property of (4R,5S)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

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Technology Process of (4R,5S)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

There total 7 articles about (4R,5S)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 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: 100.0%

: 308140-76-3
(4S,5S)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

: 308140-77-4
(4R,5S)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: With potassium carbonate; In methanol; at 0 ℃; for 12h;
DOI:10.1055/s-2000-7114

Reference yield:

: 308140-87-6
(2S,3S)-4-tert-Butyldiphenylsilyloxy-2,3-epoxy-1-(thiazol-2-yl)butan-1-one

: 308140-77-4
(4R,5S)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: 62 percent / K-selectride / tetrahydrofuran / 1 h / -78 °C

2.1: 4.2 g / NaN₃; aq. NH₄Cl / methanol / 44 h / Heating

3.1: 93 percent / p-TsOH / toluene / 0.33 h / Heating

4.1: 4-Angstroem molecular sieves; TMSTf / acetonitrile / 0.58 h / 20 °C

4.2: NaBH₄ / methanol / 0.67 h / 0 °C

4.3: 89 percent / aq. HgCl₂ / acetonitrile / 0.5 h

5.1: 100 percent / K₂CO₃ / methanol / 12 h / 0 °C

With sodium azide; TMSTf; 4 A molecular sieve; potassium tri-sec-butyl-borohydride; potassium carbonate; ammonium chloride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; toluene; acetonitrile; 1.1: Reduction / 2.1: Substitution / 3.1: Cyclization / 4.1: Methylation / 4.2: Reduction / 4.3: Hydrolysis / 5.1: Epimerization;
DOI:10.1055/s-2000-7114

Reference yield:

: 131380-35-3
(2R,3R)-4-(tert-Butyldiphenylsilyloxy)-2,3-epoxybutan-1-al

: 308140-77-4
(4R,5S)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1.1: CH₂Cl₂ / 12.33 h / -30 - 20 °C

2.1: Amberlite IR 120 / methanol / 6 h / 20 °C

3.1: 4.2 g / NaN₃; aq. NH₄Cl / methanol / 44 h / Heating

4.1: 93 percent / p-TsOH / toluene / 0.33 h / Heating

5.1: 4-Angstroem molecular sieves; TMSTf / acetonitrile / 0.58 h / 20 °C

5.2: NaBH₄ / methanol / 0.67 h / 0 °C

5.3: 89 percent / aq. HgCl₂ / acetonitrile / 0.5 h

6.1: 100 percent / K₂CO₃ / methanol / 12 h / 0 °C

With sodium azide; TMSTf; 4 A molecular sieve; Amberlite IR 120; potassium carbonate; ammonium chloride; toluene-4-sulfonic acid; In methanol; dichloromethane; toluene; acetonitrile; 1.1: Addition / 2.1: Substitution / 3.1: Substitution / 4.1: Cyclization / 5.1: Methylation / 5.2: Reduction / 5.3: Hydrolysis / 6.1: Epimerization;
DOI:10.1055/s-2000-7114