(3S,4R,5R)-5-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxypyrrolidin-2-one

Base Information

Chemical Name:(3S,4R,5R)-5-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxypyrrolidin-2-one
CAS No.:290354-73-3
Molecular Formula:C₂₁H₂₇NO₄Si
Molecular Weight:385.535
Hs Code.:

Synonyms:(3S,4R,5R)-5-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxypyrrolidin-2-one

Suppliers and Price of (3S,4R,5R)-5-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxypyrrolidin-2-one

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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 (3S,4R,5R)-5-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxypyrrolidin-2-one

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Technology Process of (3S,4R,5R)-5-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxypyrrolidin-2-one

There total 8 articles about (3S,4R,5R)-5-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxypyrrolidin-2-one 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: 89.0%

: 139877-36-4,155102-96-8,783279-99-2
(3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-one

: 58479-61-1
tert-butylchlorodiphenylsilane

: 290354-73-3
(3S,4R,5R)-5-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxypyrrolidin-2-one

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Inert atmosphere;
DOI:10.1021/acs.joc.6b00494

Reference yield: 71.0%

: 290354-72-2
(2S,3R,4R)-2-Benzyloxy-5-(tert-butyldiphenylsiloxy)-4-dibenzylamino-3-hydroxy-N-methoxy-N-methylpentanamide

: 290354-73-3
(3S,4R,5R)-5-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxypyrrolidin-2-one

Guidance literature:: With hydrogen; palladium dihydroxide; In methanol; at 20 ℃; for 72h;
DOI:10.1016/j.tetlet.2003.08.030

Reference yield:

: 290354-66-4
(2S)-3-(tert-Butyldiphenylsiloxy)-2-(dibenzylamino)propanal

: 290354-73-3
(3S,4R,5R)-5-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxypyrrolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: iPr₂NEt; n-Bu₂BOTf / diethyl ether / 1.5 h / -78 °C

1.2: 75 percent / diethyl ether / 2 h / -78 - 0 °C

2.1: Me₃Al / tetrahydrofuran / -30 °C

2.2: 91 percent / tetrahydrofuran / 18 h / -30 - 20 °C

3.1: 71 percent / H₂ / Pd(OH)2 / methanol / 72 h / 20 °C

With di-n-butylboryl trifluoromethanesulfonate; hydrogen; trimethylaluminum; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether;
DOI:10.1016/j.tetlet.2003.08.030