(2R,3S,5S)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyhexanoate

Base Information

Chemical Name:(2R,3S,5S)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyhexanoate
CAS No.:1335000-84-4
Molecular Formula:C₂₉H₄₃NO₇Si
Molecular Weight:545.748
Hs Code.:

Synonyms:(2R,3S,5S)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyhexanoate

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Chemical Property of (2R,3S,5S)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyhexanoate

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Technology Process of (2R,3S,5S)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyhexanoate

There total 5 articles about (2R,3S,5S)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyhexanoate 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: 90.0%

: 1335000-82-2
(S,E)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)hex-2-enoate

: 1335000-84-4
(2R,3S,5S)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyhexanoate

Guidance literature:: (S,E)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)hex-2-enoate; With osmium(VIII) oxide; methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); In water; toluene; tert-butyl alcohol; at 0 ℃; for 24h;

With sodium sulfite; In water; toluene; tert-butyl alcohol; for 0.75h; enantioselective reaction;
DOI:10.1016/j.tetasy.2011.06.018

Reference yield:

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

: 1335000-84-4
(2R,3S,5S)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyhexanoate

Guidance literature:: Multi-step reaction with 2 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

With 1H-imidazole; osmium(VIII) oxide; methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); In dichloromethane; water; toluene; tert-butyl alcohol; 2.1: Sharpless dihydroxylation;
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

: 1335000-84-4
(2R,3S,5S)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyhexanoate

Guidance literature:: Multi-step reaction with 3 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

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