(1R,2'R,3'R,4'R,5'S)-1-[4'-azido-3',5'-bis(tert-butyldimethylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-bis-phenylsulfanyl-ethanol

Base Information

Chemical Name:(1R,2'R,3'R,4'R,5'S)-1-[4'-azido-3',5'-bis(tert-butyldimethylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-bis-phenylsulfanyl-ethanol
CAS No.:864941-66-2
Molecular Formula:C₃₁H₄₉N₃O₄S₂Si₂
Molecular Weight:648.051
Hs Code.:

Synonyms:(1R,2'R,3'R,4'R,5'S)-1-[4'-azido-3',5'-bis(tert-butyldimethylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-bis-phenylsulfanyl-ethanol

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Chemical Property of (1R,2'R,3'R,4'R,5'S)-1-[4'-azido-3',5'-bis(tert-butyldimethylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-bis-phenylsulfanyl-ethanol

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Technology Process of (1R,2'R,3'R,4'R,5'S)-1-[4'-azido-3',5'-bis(tert-butyldimethylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-bis-phenylsulfanyl-ethanol

There total 8 articles about (1R,2'R,3'R,4'R,5'S)-1-[4'-azido-3',5'-bis(tert-butyldimethylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-bis-phenylsulfanyl-ethanol 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:

: 864941-65-1
(2R,3R,4R,5S)-4-azido-3,5-bis(tert-butyldimethylsilanyloxy)-tetrahydropyran-2-carbaldehyde

: 3561-67-9
bis(phenylthio)methane

: (1S,2'R,3'R,4'R,5'S)-1-[4'-azido-3',5'-bis(tert-butyldimethylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-bis-phenylsulfanyl-ethanol

: 864941-66-2
(1R,2'R,3'R,4'R,5'S)-1-[4'-azido-3',5'-bis(tert-butyldimethylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-bis-phenylsulfanyl-ethanol

Guidance literature:: bis(phenylthio)methane; With n-butyllithium; In tetrahydrofuran; hexane; at -10 ℃; for 0.416667h;

(2R,3R,4R,5S)-4-azido-3,5-bis(tert-butyldimethylsilanyloxy)-tetrahydropyran-2-carbaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;
DOI:10.1021/jo050727b

Reference yield:

: (3R,4R,5S)-4-Azido-3,5-dihydroxy-tetrahydro-pyran-2-carbonitrile

: 864941-66-2
(1R,2'R,3'R,4'R,5'S)-1-[4'-azido-3',5'-bis(tert-butyldimethylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-bis-phenylsulfanyl-ethanol

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium hydroxide / methanol; H₂O / 3 h / 45 °C

2.1: 2.72 g / TMSCl / 13 h / 20 °C

3.1: 95 percent / imidazole / CH₂Cl₂ / 15 h / 20 °C

4.1: AlMe₃ / CH₂Cl₂; toluene / 0.67 h / 0 °C

4.2: 68 percent / CH₂Cl₂; toluene / 22 h / 0 - 20 °C

5.1: DIBAL-H / toluene; hexane / 2 h / -78 °C

6.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

7.1: BuLi / tetrahydrofuran; hexane / 0.42 h / -10 °C

7.2: 161 mg / tetrahydrofuran; hexane / 0.5 h / -78 °C

With 1H-imidazole; sodium hydroxide; n-butyllithium; chloro-trimethyl-silane; trimethylaluminum; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene;
DOI:10.1021/jo050727b

Reference yield:

: 864941-81-1
(3R,4R,5S)-4-Azido-3,5-dihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 864941-66-2
(1R,2'R,3'R,4'R,5'S)-1-[4'-azido-3',5'-bis(tert-butyldimethylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-bis-phenylsulfanyl-ethanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / imidazole / CH₂Cl₂ / 15 h / 20 °C

2.1: AlMe₃ / CH₂Cl₂; toluene / 0.67 h / 0 °C

2.2: 68 percent / CH₂Cl₂; toluene / 22 h / 0 - 20 °C

3.1: DIBAL-H / toluene; hexane / 2 h / -78 °C

4.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

5.1: BuLi / tetrahydrofuran; hexane / 0.42 h / -10 °C

5.2: 161 mg / tetrahydrofuran; hexane / 0.5 h / -78 °C

With 1H-imidazole; n-butyllithium; trimethylaluminum; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1021/jo050727b