(2S,3S,5S)-ethyl 5-((tert-butyldiphenylsilyloxy)methyl)-3-hydroxypyrrolidine-2-carboxylate

Base Information

Chemical Name:(2S,3S,5S)-ethyl 5-((tert-butyldiphenylsilyloxy)methyl)-3-hydroxypyrrolidine-2-carboxylate
CAS No.:1335000-86-6
Molecular Formula:C₂₄H₃₃NO₄Si
Molecular Weight:427.616
Hs Code.:

Synonyms:(2S,3S,5S)-ethyl 5-((tert-butyldiphenylsilyloxy)methyl)-3-hydroxypyrrolidine-2-carboxylate

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Chemical Property of (2S,3S,5S)-ethyl 5-((tert-butyldiphenylsilyloxy)methyl)-3-hydroxypyrrolidine-2-carboxylate

Chemical Property:

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Technology Process of (2S,3S,5S)-ethyl 5-((tert-butyldiphenylsilyloxy)methyl)-3-hydroxypyrrolidine-2-carboxylate

There total 6 articles about (2S,3S,5S)-ethyl 5-((tert-butyldiphenylsilyloxy)methyl)-3-hydroxypyrrolidine-2-carboxylate 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:

: C₂HF₃O₂*C₃₁H₄₁NO₇SSi

: 1335000-86-6
(2S,3S,5S)-ethyl 5-((tert-butyldiphenylsilyloxy)methyl)-3-hydroxypyrrolidine-2-carboxylate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 3h;
DOI:10.1016/j.tetasy.2011.06.018

Reference yield:

: 905718-71-0
(S,E)-tert-butyl-4-(4-ethoxy-4-oxobut-2-enyl)-2,2-dimethyloxazolidine-3-carboxylate

: 1335000-86-6
(2S,3S,5S)-ethyl 5-((tert-butyldiphenylsilyloxy)methyl)-3-hydroxypyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: methanol / 1 h / 20 °C

1.2: 0.5 h

2.1: 1H-imidazole / dichloromethane / 4 h / 0 °C

3.1: osmium(VIII) oxide; methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III) / water; toluene; tert-butyl alcohol / 24 h / 0 °C

3.2: 0.75 h

4.1: triethylamine / dichloromethane / 72 h / 0 - 5 °C

5.1: dichloromethane / 2 h / 20 °C

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C

With 1H-imidazole; methanol; osmium(VIII) oxide; methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); In dichloromethane; water; toluene; tert-butyl alcohol; 3.1: Sharpless dihydroxylation;
DOI:10.1016/j.tetasy.2011.06.018

Reference yield:

: 5-tert-butoxycarbonylamino-6-hydroxy-hex-2-enoic acid ethyl ester

: 1335000-86-6
(2S,3S,5S)-ethyl 5-((tert-butyldiphenylsilyloxy)methyl)-3-hydroxypyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1H-imidazole / dichloromethane / 4 h / 0 °C

2.1: osmium(VIII) oxide; methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III) / water; toluene; tert-butyl alcohol / 24 h / 0 °C

2.2: 0.75 h

3.1: triethylamine / dichloromethane / 72 h / 0 - 5 °C

4.1: dichloromethane / 2 h / 20 °C

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C

With 1H-imidazole; osmium(VIII) oxide; methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); In dichloromethane; water; toluene; tert-butyl alcohol; 2.1: Sharpless dihydroxylation;
DOI:10.1016/j.tetasy.2011.06.018