(2R/S,4R)-4-[(tert-butyldiphenylsilyl)oxy]methyl-2-hydroxytetrahydrofuran

Base Information

Chemical Name:(2R/S,4R)-4-[(tert-butyldiphenylsilyl)oxy]methyl-2-hydroxytetrahydrofuran
CAS No.:251940-57-5
Molecular Formula:C₂₁H₂₈O₃Si
Molecular Weight:356.537
Hs Code.:

Synonyms:(2R/S,4R)-4-[(tert-butyldiphenylsilyl)oxy]methyl-2-hydroxytetrahydrofuran

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R/S,4R)-4-[(tert-butyldiphenylsilyl)oxy]methyl-2-hydroxytetrahydrofuran

Chemical Property:

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Technology Process of (2R/S,4R)-4-[(tert-butyldiphenylsilyl)oxy]methyl-2-hydroxytetrahydrofuran

There total 3 articles about (2R/S,4R)-4-[(tert-butyldiphenylsilyl)oxy]methyl-2-hydroxytetrahydrofuran 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: 95.0%

: 251940-56-4
(2R,4S)-4-[(tert-butyldiphenylsilyl)oxy]methyl-1,2,5-pentanetriol

: 251940-57-5
(2R/S,4R)-4-[(tert-butyldiphenylsilyl)oxy]methyl-2-hydroxytetrahydrofuran

Guidance literature:: With sodium periodate; In water; tert-butyl alcohol; at 20 ℃; for 2.5h;
DOI:10.1271/bbb.63.1605

Reference yield:

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

: 251940-57-5
(2R/S,4R)-4-[(tert-butyldiphenylsilyl)oxy]methyl-2-hydroxytetrahydrofuran

Guidance literature:: Multi-step reaction with 3 steps

1.1: DIBAL-H / toluene / 1 h / -75 °C

1.2: 100 percent / NaBH₄ / ethanol / 1 h / 20 °C

2.1: 70 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 65 °C

3.1: 95 percent / NaIO₄ / 2-methyl-propan-2-ol; H₂O / 2.5 h / 20 °C

With sodium periodate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; In methanol; water; toluene; tert-butyl alcohol; 1.1: Reduction / 1.2: Reduction / 2.1: Substitution / 3.1: Oxidation;
DOI:10.1271/bbb.63.1605

Reference yield:

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

: 251940-57-5
(2R/S,4R)-4-[(tert-butyldiphenylsilyl)oxy]methyl-2-hydroxytetrahydrofuran

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 65 °C

2: 95 percent / NaIO₄ / 2-methyl-propan-2-ol; H₂O / 2.5 h / 20 °C

With sodium periodate; pyridinium p-toluenesulfonate; In methanol; water; tert-butyl alcohol; 1: Substitution / 2: Oxidation;
DOI:10.1271/bbb.63.1605