(2R,3S,4R,5R,6R)-3-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)-2-(2-tert-butyldiphenylsiloxyethyl)-6-(triphenylmethoxymethyl)tetrahydropyran

Base Information

Chemical Name:(2R,3S,4R,5R,6R)-3-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)-2-(2-tert-butyldiphenylsiloxyethyl)-6-(triphenylmethoxymethyl)tetrahydropyran
CAS No.:299926-69-5
Molecular Formula:C₅₇H₇₈O₇Si₃
Molecular Weight:959.499
Hs Code.:

(2R,3S,4R,5R,6R)-3-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)-2-(2-tert-butyldiphenylsiloxyethyl)-6-(triphenylmethoxymethyl)tetrahydropyran

Synonyms:(2R,3S,4R,5R,6R)-3-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)-2-(2-tert-butyldiphenylsiloxyethyl)-6-(triphenylmethoxymethyl)tetrahydropyran

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Chemical Property of (2R,3S,4R,5R,6R)-3-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)-2-(2-tert-butyldiphenylsiloxyethyl)-6-(triphenylmethoxymethyl)tetrahydropyran

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Technology Process of (2R,3S,4R,5R,6R)-3-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)-2-(2-tert-butyldiphenylsiloxyethyl)-6-(triphenylmethoxymethyl)tetrahydropyran

There total 8 articles about (2R,3S,4R,5R,6R)-3-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)-2-(2-tert-butyldiphenylsiloxyethyl)-6-(triphenylmethoxymethyl)tetrahydropyran 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%

: 108-24-7
acetic anhydride

: 299926-68-4
(2R,3S,4R,5R,6R)-4,5-bis(tert-butyldimethylsilyloxy)-3-hydroxy-2-(2-tert-butyldiphenylsiloxyethyl)-6-(triphenylmethoxymethyl)tetrahydropyran

: 299926-69-5
(2R,3S,4R,5R,6R)-3-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)-2-(2-tert-butyldiphenylsiloxyethyl)-6-(triphenylmethoxymethyl)tetrahydropyran

Guidance literature:: With dmap; In acetonitrile; at 60 ℃; for 15h;
DOI:10.1021/jo0002339

Reference yield:

: 122350-80-5
1,5-anhydro-2-deoxy-6-O-trityl-D-arabino-hex-1-enitol

: 299926-69-5
(2R,3S,4R,5R,6R)-3-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)-2-(2-tert-butyldiphenylsiloxyethyl)-6-(triphenylmethoxymethyl)tetrahydropyran

Guidance literature:: Multi-step reaction with 6 steps

1.1: 85 percent / imidazole / dimethylformamide / 12 h / 60 °C

2.1: dimethyldioxirane / CH₂Cl₂; acetone / 0 - 20 °C

2.2: Et₃N / CH₂Cl₂ / 1.75 h / -20 °C

3.1: 2.56 g / Et₃N; DMAP / toluene / 2 h / 20 °C

4.1: Bu₃SnH; AIBN / chlorobenzene / 4 h / Heating

4.2: 55 percent / aq. H₂O₂; KF; KHCO₃ / methanol; tetrahydrofuran / 264 h / 20 °C

5.1: 100 percent / imidazole / dimethylformamide / 20 °C

6.1: 100 percent / DMAP / acetonitrile / 15 h / 60 °C

With 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 3,3-dimethyldioxirane; triethylamine; In dichloromethane; N,N-dimethyl-formamide; chlorobenzene; acetone; toluene; acetonitrile; 1.1: Condensation / 2.1: Oxidation / 2.2: Addition / 3.1: Condensation / 4.1: Reduction / 4.2: Tamao oxidation / 5.1: Condensation / 6.1: Acetylation;
DOI:10.1021/jo0002339

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 299926-69-5
(2R,3S,4R,5R,6R)-3-acetoxy-4,5-bis(tert-butyldimethylsilyloxy)-2-(2-tert-butyldiphenylsiloxyethyl)-6-(triphenylmethoxymethyl)tetrahydropyran

Guidance literature:: Multi-step reaction with 6 steps

1.1: 85 percent / imidazole / dimethylformamide / 12 h / 60 °C

2.1: dimethyldioxirane / CH₂Cl₂; acetone / 0 - 20 °C

2.2: Et₃N / CH₂Cl₂ / 1.75 h / -20 °C

3.1: 2.56 g / Et₃N; DMAP / toluene / 2 h / 20 °C

4.1: Bu₃SnH; AIBN / chlorobenzene / 4 h / Heating

4.2: 55 percent / aq. H₂O₂; KF; KHCO₃ / methanol; tetrahydrofuran / 264 h / 20 °C

5.1: 100 percent / imidazole / dimethylformamide / 20 °C

6.1: 100 percent / DMAP / acetonitrile / 15 h / 60 °C

With 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 3,3-dimethyldioxirane; triethylamine; In dichloromethane; N,N-dimethyl-formamide; chlorobenzene; acetone; toluene; acetonitrile; 1.1: Condensation / 2.1: Oxidation / 2.2: Addition / 3.1: Condensation / 4.1: Reduction / 4.2: Tamao oxidation / 5.1: Condensation / 6.1: Acetylation;
DOI:10.1021/jo0002339