(2S,3R)-2-(tert-butyldiphenylsilanyloxymethyl)-3-(2'-hydroxyethyl)tetrahydrofuran-3-ol

Base Information

Chemical Name:(2S,3R)-2-(tert-butyldiphenylsilanyloxymethyl)-3-(2'-hydroxyethyl)tetrahydrofuran-3-ol
CAS No.:544687-58-3
Molecular Formula:C₂₃H₃₂O₄Si
Molecular Weight:400.59
Hs Code.:

Synonyms:(2S,3R)-2-(tert-butyldiphenylsilanyloxymethyl)-3-(2'-hydroxyethyl)tetrahydrofuran-3-ol

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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 (2S,3R)-2-(tert-butyldiphenylsilanyloxymethyl)-3-(2'-hydroxyethyl)tetrahydrofuran-3-ol

Chemical Property:

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Technology Process of (2S,3R)-2-(tert-butyldiphenylsilanyloxymethyl)-3-(2'-hydroxyethyl)tetrahydrofuran-3-ol

There total 5 articles about (2S,3R)-2-(tert-butyldiphenylsilanyloxymethyl)-3-(2'-hydroxyethyl)tetrahydrofuran-3-ol 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:

: (2R,3R)-3-[2-(9-Bora-bicyclo[3.3.1]non-9-yl)-ethyl]-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

: 544687-58-3
(2S,3R)-2-(tert-butyldiphenylsilanyloxymethyl)-3-(2'-hydroxyethyl)tetrahydrofuran-3-ol

Guidance literature:: With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; diethyl ether; water; at 0 ℃; for 2h;
DOI:10.1021/jo0341620

Reference yield:

: 127761-83-5
1,4-anhydro-5-O-(tert-butyldiphenylsilyl)-2-deoxy-D-erythro-pent-1-enitol

: 544687-58-3
(2S,3R)-2-(tert-butyldiphenylsilanyloxymethyl)-3-(2'-hydroxyethyl)tetrahydrofuran-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 87 percent / hydrogen / Pd/C / methanol / 20 °C

2: 90 percent / sodium acetate; pyridinium chlorochromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 20 °C

3: 94 percent / tetrahydrofuran / 2 h / -78 °C

4: tetrahydrofuran; diethyl ether / 3 h / 0 - 20 °C

5: 3.15 g / aqueous NaOH; H₂O₂ / tetrahydrofuran; diethyl ether; H₂O / 2 h / 0 °C

With sodium hydroxide; 4 A molecular sieve; hydrogen; dihydrogen peroxide; sodium acetate; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;
DOI:10.1021/jo0341620

Reference yield:

: 401813-15-8
(2S,3S)-2-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-3-ol

: 544687-58-3
(2S,3R)-2-(tert-butyldiphenylsilanyloxymethyl)-3-(2'-hydroxyethyl)tetrahydrofuran-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / sodium acetate; pyridinium chlorochromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 20 °C

2: 94 percent / tetrahydrofuran / 2 h / -78 °C

3: tetrahydrofuran; diethyl ether / 3 h / 0 - 20 °C

4: 3.15 g / aqueous NaOH; H₂O₂ / tetrahydrofuran; diethyl ether; H₂O / 2 h / 0 °C

With sodium hydroxide; 4 A molecular sieve; dihydrogen peroxide; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; water;
DOI:10.1021/jo0341620