(2S,3R)-3-(tert-butyldiphenylsilyl)oxy-2-[diazo(ethoxycarbonyl)methyl]-2-hydroxy-4-butanolide

Base Information

Chemical Name:(2S,3R)-3-(tert-butyldiphenylsilyl)oxy-2-[diazo(ethoxycarbonyl)methyl]-2-hydroxy-4-butanolide
CAS No.:207124-17-2
Molecular Formula:C₂₄H₂₈N₂O₆Si
Molecular Weight:468.582
Hs Code.:

Synonyms:(2S,3R)-3-(tert-butyldiphenylsilyl)oxy-2-[diazo(ethoxycarbonyl)methyl]-2-hydroxy-4-butanolide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3R)-3-(tert-butyldiphenylsilyl)oxy-2-[diazo(ethoxycarbonyl)methyl]-2-hydroxy-4-butanolide

Chemical Property:

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Technology Process of (2S,3R)-3-(tert-butyldiphenylsilyl)oxy-2-[diazo(ethoxycarbonyl)methyl]-2-hydroxy-4-butanolide

There total 8 articles about (2S,3R)-3-(tert-butyldiphenylsilyl)oxy-2-[diazo(ethoxycarbonyl)methyl]-2-hydroxy-4-butanolide 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: 68.0%

: 207124-12-7
4-ethyl 1-methyl [2S,2(1R)]-2-[2-(tert-butyldiphenylsilyl)oxy-1-[3-(methoxymethoxy)propionyl]oxyethyl]-3-diazo-2-hydroxybutanediote

: 207124-17-2
(2S,3R)-3-(tert-butyldiphenylsilyl)oxy-2-[diazo(ethoxycarbonyl)methyl]-2-hydroxy-4-butanolide

Guidance literature:: With potassium carbonate; In methanol; at 0 ℃; for 1h;
DOI:10.1002/chem.200601212

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 207124-17-2
(2S,3R)-3-(tert-butyldiphenylsilyl)oxy-2-[diazo(ethoxycarbonyl)methyl]-2-hydroxy-4-butanolide

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / DMAP, pyridine / CH₂Cl₂ / 20 h

2: 89 percent / EDCI, DMAP / CH₂Cl₂ / 5 h

3: 85 percent / H₂ / 20percent Pd(OH)2/C / methanol / 20 h / Heating

4: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 8 h

5: LiHMDS / tetrahydrofuran / 3 h / -78 °C

6: K₂CO₃ / methanol / 0 °C

With pyridine; dmap; hydrogen; potassium carbonate; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0040-4039(98)00203-2

Reference yield:

: 207124-05-8
(2S,3R)-2-Benzyloxy-3,4-dihydroxy-butyric acid methyl ester

: 207124-17-2
(2S,3R)-3-(tert-butyldiphenylsilyl)oxy-2-[diazo(ethoxycarbonyl)methyl]-2-hydroxy-4-butanolide

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / DMAP, pyridine / CH₂Cl₂ / 20 h

2: 89 percent / EDCI, DMAP / CH₂Cl₂ / 5 h

3: 85 percent / H₂ / 20percent Pd(OH)2/C / methanol / 20 h / Heating

4: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 8 h

5: LiHMDS / tetrahydrofuran / 3 h / -78 °C

6: K₂CO₃ / methanol / 0 °C

With pyridine; dmap; hydrogen; potassium carbonate; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0040-4039(98)00203-2