(2R,3R,4R)-3,4-bis(tert-butyldimethylsiloxy)-3,4-dihydro-2-(triphenylmethoxymethyl)-2H-pyran

Base Information

Chemical Name:(2R,3R,4R)-3,4-bis(tert-butyldimethylsiloxy)-3,4-dihydro-2-(triphenylmethoxymethyl)-2H-pyran
CAS No.:288584-98-5
Molecular Formula:C₃₇H₅₂O₄Si₂
Molecular Weight:616.988
Hs Code.:

Synonyms:(2R,3R,4R)-3,4-bis(tert-butyldimethylsiloxy)-3,4-dihydro-2-(triphenylmethoxymethyl)-2H-pyran

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Chemical Property of (2R,3R,4R)-3,4-bis(tert-butyldimethylsiloxy)-3,4-dihydro-2-(triphenylmethoxymethyl)-2H-pyran

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Technology Process of (2R,3R,4R)-3,4-bis(tert-butyldimethylsiloxy)-3,4-dihydro-2-(triphenylmethoxymethyl)-2H-pyran

There total 1 articles about (2R,3R,4R)-3,4-bis(tert-butyldimethylsiloxy)-3,4-dihydro-2-(triphenylmethoxymethyl)-2H-pyran 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: 85.0%

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

: 18162-48-6
tert-butyldimethylsilyl chloride

: 288584-98-5
(2R,3R,4R)-3,4-bis(tert-butyldimethylsiloxy)-3,4-dihydro-2-(triphenylmethoxymethyl)-2H-pyran

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)00556-6

Reference yield: 66.0%

: 645-96-5
Benzeneselenol

: 288584-98-5
(2R,3R,4R)-3,4-bis(tert-butyldimethylsiloxy)-3,4-dihydro-2-(triphenylmethoxymethyl)-2H-pyran

: 288584-99-6
phenyl 3,4-bis-O-tert-butyldimethylsilyl-6-O-trityl-1-seleno-β-D-glucose

Guidance literature:: (2R,3R,4R)-3,4-bis(tert-butyldimethylsiloxy)-3,4-dihydro-2-(triphenylmethoxymethyl)-2H-pyran; With 3,3-dimethyldioxirane; In dichloromethane;

Benzeneselenol; With triethylamine; In dichloromethane;
DOI:10.1016/S0040-4039(00)00556-6

Reference yield:

: 288584-98-5
(2R,3R,4R)-3,4-bis(tert-butyldimethylsiloxy)-3,4-dihydro-2-(triphenylmethoxymethyl)-2H-pyran

: 299926-70-8
(2R,3R,4S,5S,6R)-3-acetoxy-4,5-dihydroxy-2-hydroxyethyl-6-(triphenylmethoxymethyl)tetrahydropyran

Guidance literature:: Multi-step reaction with 6 steps

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

1.2: Et₃N / CH₂Cl₂ / 1.75 h / -20 °C

2.1: 2.56 g / Et₃N; DMAP / toluene / 2 h / 20 °C

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

3.2: 55 percent / aq. H₂O₂; KF; KHCO₃ / methanol; tetrahydrofuran / 264 h / 20 °C

4.1: 100 percent / imidazole / dimethylformamide / 20 °C

5.1: 100 percent / DMAP / acetonitrile / 15 h / 60 °C

6.1: 100 percent / TBAF; AcOH / tetrahydrofuran / 24 h / 20 °C

With 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; 3,3-dimethyldioxirane; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; chlorobenzene; acetone; toluene; acetonitrile; 1.1: Oxidation / 1.2: Addition / 2.1: Condensation / 3.1: Reduction / 3.2: Tamao oxidation / 4.1: Condensation / 5.1: Acetylation / 6.1: Substitution;
DOI:10.1021/jo0002339