Acetic acid (2R,3R,4S,5S,6R)-2-((S)-1-benzyloxy-ethyl)-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-((S)-1-benzyloxy-ethyl)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3,5-dimethyl-tetrahydro-pyran-4-yl ester
CAS No.:270585-30-3
Molecular Formula:C₃₆H₄₈O₅Si
Molecular Weight:588.86
Hs Code.:

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

There total 7 articles about Acetic acid (2R,3R,4S,5S,6R)-2-((S)-1-benzyloxy-ethyl)-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: 52.0%

: 270585-29-0
Acetic acid (S)-2-benzyloxy-1-{(E)-(1R,2R)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methyl-pent-3-enyloxy}-propyl ester

: {2-[(2R,3S,4S,5S,6R)-6-((S)-1-Benzyloxy-ethyl)-4-fluoro-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane

: 270585-30-3
Acetic acid (2R,3R,4S,5S,6R)-2-((S)-1-benzyloxy-ethyl)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3,5-dimethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With acetic acid; boron trifluoride diethyl etherate; In Petroleum ether; at 0 ℃; for 2h;
DOI:10.1021/ol005646a

Reference yield:

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

: 270585-30-3
Acetic acid (2R,3R,4S,5S,6R)-2-((S)-1-benzyloxy-ethyl)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3,5-dimethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 6 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

With pyridine; dmap; Chloro-oxo-acetic acid; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; boron trifluoride diethyl etherate; In hexane; dichloromethane; 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;
DOI:10.1021/ol005646a

Reference yield:

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

: 270585-30-3
Acetic acid (2R,3R,4S,5S,6R)-2-((S)-1-benzyloxy-ethyl)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3,5-dimethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 5 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

With pyridine; dmap; diisobutylaluminium hydride; acetic acid; dicyclohexyl-carbodiimide; boron trifluoride diethyl etherate; In hexane; dichloromethane; Petroleum ether; 1.1: coupling / 2.1: coupling / 2.2: coupling / 3.1: Reduction / 4.1: Acetylation / 5.1: Prins cyclization;
DOI:10.1021/ol005646a