(3R,5R)-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-5-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatriciclo[5.2.1.0^1,5]decane-4-carbonyl]-isoxazolidine-3-carboxylic acid ethyl ester

Base Information

• Chemical Name: (3R,5R)-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-5-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatriciclo[5.2.1.0^1,5]decane-4-carbonyl]-isoxazolidine-3-carboxylic acid ethyl ester
• CAS No.: 455334-17-5
• Molecular Formula: C₄₁H₅₆N₂O₁₀SSi
• Molecular Weight: 797.055

Synonyms:

Chemical Property of (3R,5R)-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-5-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatriciclo[5.2.1.0^1,5]decane-4-carbonyl]-isoxazolidine-3-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (3R,5R)-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-5-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatriciclo[5.2.1.0^1,5]decane-4-carbonyl]-isoxazolidine-3-carboxylic acid ethyl ester

There total 1 articles about (3R,5R)-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-5-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatriciclo[5.2.1.0^1,5]decane-4-carbonyl]-isoxazolidine-3-carboxylic acid ethyl ester 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: 57.0%

glyoxylic acid ethyl ester (924-44-7) + acrylcamphorsultam (94594-91-9) + 5-(tert-butyldiphenylsilyl)-1-deoxy-1-hydroxyamino-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranose (557794-46-4) → (3R,5R)-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-5-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatriciclo[5.2.1.01,5]decane-4-carbonyl]-isoxazolidine-3-carboxylic acid ethyl ester (455334-17-5) + (3S,5R)-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-5-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatriciclo[5.2.1.01,5]decane-4-carbonyl]-isoxazolidine-3-carboxylic acid ethyl ester (455334-19-7)

Guidance literature:

In toluene; at 75 ℃; for 40h;

DOI:10.1016/S0957-4166(02)00072-1

Reference yield:

(3R,5R)-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-5-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatriciclo[5.2.1.01,5]decane-4-carbonyl]-isoxazolidine-3-carboxylic acid ethyl ester (455334-17-5) → (2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: conc. HCl / ethanol / 20 °C

2: imidazole / dimethylformamide / 3 h / 70 °C

With 1H-imidazole; hydrogenchloride; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(02)00072-1

Reference yield:

(3R,5R)-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-5-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatriciclo[5.2.1.01,5]decane-4-carbonyl]-isoxazolidine-3-carboxylic acid ethyl ester (455334-17-5) → 1-tert-butyl 2-ethyl (2R,4R)-4-[(tert-butyldiphenylsilyl)oxy]-5-oxo-pyrrolidine-1,2-dicarboxylate

Guidance literature:

Multi-step reaction with 3 steps

1: conc. HCl / ethanol / 20 °C

2: imidazole / dimethylformamide / 3 h / 70 °C

3: 0.187 g / Et₃N; DMAP / CH₂Cl₂ / 20 °C

With 1H-imidazole; hydrogenchloride; dmap; triethylamine; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(02)00072-1

upstream raw materials:

glyoxylic acid ethyl ester

acrylcamphorsultam

5-(tert-butyldiphenylsilyl)-1-deoxy-1-hydroxyamino-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranose

Downstream raw materials:

(2R,4R)-4-Hydroxy-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester

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