Acetic acid (2R,3R,4S,5S,6R)-2-acetyl-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3,5-dimethyl-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Acetic acid (2R,3R,4S,5S,6R)-2-acetyl-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3,5-dimethyl-tetrahydro-pyran-4-yl ester
CAS No.:270585-32-5
Molecular Formula:C₂₉H₄₀O₅Si
Molecular Weight:496.719
Hs Code.:

Synonyms:Acetic acid (2R,3R,4S,5S,6R)-2-acetyl-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3,5-dimethyl-tetrahydro-pyran-4-yl ester

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Chemical Property of Acetic acid (2R,3R,4S,5S,6R)-2-acetyl-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3,5-dimethyl-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2R,3R,4S,5S,6R)-2-acetyl-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3,5-dimethyl-tetrahydro-pyran-4-yl ester

There total 9 articles about Acetic acid (2R,3R,4S,5S,6R)-2-acetyl-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3,5-dimethyl-tetrahydro-pyran-4-yl 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: 100.0%

: Acetic acid (2R,3S,4S,5R,6R)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-((S)-1-hydroxy-ethyl)-3,5-dimethyl-tetrahydro-pyran-4-yl ester

: 270585-32-5
Acetic acid (2R,3R,4S,5S,6R)-2-acetyl-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3,5-dimethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With Chloro-oxo-acetic acid; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 23 ℃;
DOI:10.1021/ol005646a

Reference yield:

: 3-(tert-butyldiphenylsilyloxy)-propan-1,3-diol

: 270585-32-5
Acetic acid (2R,3R,4S,5S,6R)-2-acetyl-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3,5-dimethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: oxalylchloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 23 °C

2.1: 20.92 g / petroleum ether / 72 h / 0 °C

3.1: DCC / CH₂Cl₂ / 0.08 h / 0 °C

3.2: 17.72 g / DMAP / CH₂Cl₂ / 24 h / 20 °C

4.1: DIBAL-H / CH₂Cl₂; hexane / 0.75 h / -78 °C

5.1: 108 mg / DMAP; pyridine / CH₂Cl₂; hexane / -78 - 0 °C

6.1: 52 percent / acetic acid / BF₃*Et₂O / petroleum ether / 2 h / 0 °C

7.1: 100 percent / hydrogen / Pd(OH)2/C / ethyl acetate / 7 h / 760.05 Torr

8.1: 100 percent / oxalylchloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 23 °C

With pyridine; dmap; Chloro-oxo-acetic acid; hydrogen; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; palladium dihydroxide; boron trifluoride diethyl etherate; In hexane; dichloromethane; ethyl acetate; Petroleum ether; 1.1: Swern oxidation / 2.1: coupling / 3.1: coupling / 3.2: coupling / 4.1: Reduction / 5.1: Acetylation / 6.1: Prins cyclization / 7.1: Catalytic hydrogenation / 8.1: Swern oxidation;
DOI:10.1021/ol005646a

Reference yield:

: 112897-03-7
3-(tert-butyldiphenylsilyloxy)-1-propanal

: 270585-32-5
Acetic acid (2R,3R,4S,5S,6R)-2-acetyl-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3,5-dimethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 20.92 g / petroleum ether / 72 h / 0 °C

2.1: DCC / CH₂Cl₂ / 0.08 h / 0 °C

2.2: 17.72 g / DMAP / CH₂Cl₂ / 24 h / 20 °C

3.1: DIBAL-H / CH₂Cl₂; hexane / 0.75 h / -78 °C

4.1: 108 mg / DMAP; pyridine / CH₂Cl₂; hexane / -78 - 0 °C

5.1: 52 percent / acetic acid / BF₃*Et₂O / petroleum ether / 2 h / 0 °C

6.1: 100 percent / hydrogen / Pd(OH)2/C / ethyl acetate / 7 h / 760.05 Torr

7.1: 100 percent / oxalylchloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 23 °C

With pyridine; dmap; Chloro-oxo-acetic acid; hydrogen; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; palladium dihydroxide; boron trifluoride diethyl etherate; In hexane; dichloromethane; ethyl acetate; Petroleum ether; 1.1: coupling / 2.1: coupling / 2.2: coupling / 3.1: Reduction / 4.1: Acetylation / 5.1: Prins cyclization / 6.1: Catalytic hydrogenation / 7.1: Swern oxidation;
DOI:10.1021/ol005646a