(2R,4S)-2-[(tert-butyldiphenylsilyl)oxy]methyl-5-trityloxy-1,4-pentanediol

Base Information

Chemical Name:(2R,4S)-2-[(tert-butyldiphenylsilyl)oxy]methyl-5-trityloxy-1,4-pentanediol
CAS No.:251940-55-3
Molecular Formula:C₄₁H₄₆O₄Si
Molecular Weight:630.899
Hs Code.:

Synonyms:(2R,4S)-2-[(tert-butyldiphenylsilyl)oxy]methyl-5-trityloxy-1,4-pentanediol

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Chemical Property of (2R,4S)-2-[(tert-butyldiphenylsilyl)oxy]methyl-5-trityloxy-1,4-pentanediol

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Technology Process of (2R,4S)-2-[(tert-butyldiphenylsilyl)oxy]methyl-5-trityloxy-1,4-pentanediol

There total 3 articles about (2R,4S)-2-[(tert-butyldiphenylsilyl)oxy]methyl-5-trityloxy-1,4-pentanediol 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%

: 251940-54-2
(3S,5S)-3-[(tert-butyldiphenylsilyl)oxy]methyl-5-trityloxymethyldihydro-2(3H)-furanone

: 251940-55-3
(2R,4S)-2-[(tert-butyldiphenylsilyl)oxy]methyl-5-trityloxy-1,4-pentanediol

Guidance literature:: (3S,5S)-3-[(tert-butyldiphenylsilyl)oxy]methyl-5-trityloxymethyldihydro-2(3H)-furanone; With diisobutylaluminium hydride; In toluene; at -75 ℃; for 1h;

With sodium tetrahydroborate; In ethanol; at 20 ℃; for 1h;
DOI:10.1271/bbb.63.1605

Reference yield:

: 73968-62-4
(5S)-5-[(trityloxy)methyl]tetrahydro-2-furanone

: 251940-55-3
(2R,4S)-2-[(tert-butyldiphenylsilyl)oxy]methyl-5-trityloxy-1,4-pentanediol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 45 percent / nBuLi; diisorpopylamine / tetrahydrofuran / 0.5 h / -75 °C

2.1: 65 percent / imidazole / dimethylformamide / 1 h / 20 °C

3.1: DIBAL-H / toluene / 1 h / -75 °C

3.2: 100 percent / NaBH₄ / ethanol / 1 h / 20 °C

With 1H-imidazole; n-butyllithium; diisobutylaluminium hydride; diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 1.1: Condensation / 2.1: silylation / 3.1: Reduction / 3.2: Reduction;
DOI:10.1271/bbb.63.1605

Reference yield:

: 251940-53-1
(3R/S,5S)-3-hydroxymethyl-5-trityloxymethyldihydro-2(3H)-furanone

: 251940-55-3
(2R,4S)-2-[(tert-butyldiphenylsilyl)oxy]methyl-5-trityloxy-1,4-pentanediol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 65 percent / imidazole / dimethylformamide / 1 h / 20 °C

2.1: DIBAL-H / toluene / 1 h / -75 °C

2.2: 100 percent / NaBH₄ / ethanol / 1 h / 20 °C

With 1H-imidazole; diisobutylaluminium hydride; In N,N-dimethyl-formamide; toluene; 1.1: silylation / 2.1: Reduction / 2.2: Reduction;
DOI:10.1271/bbb.63.1605