(2R,3S,5S)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-(tosyloxy)hexanoate

Base Information

Chemical Name:(2R,3S,5S)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-(tosyloxy)hexanoate
CAS No.:1335000-85-5
Molecular Formula:C₃₆H₄₉NO₉SSi
Molecular Weight:699.938
Hs Code.:

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

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

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

There total 6 articles about (2R,3S,5S)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-(tosyloxy)hexanoate 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: 75.0%

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

: 98-59-9
p-toluenesulfonyl chloride

: 1335000-85-5
(2R,3S,5S)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-(tosyloxy)hexanoate

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 5 ℃; for 72h; regioselective reaction;
DOI:10.1016/j.tetasy.2011.06.018

Reference yield:

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

: 1335000-85-5
(2R,3S,5S)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-(tosyloxy)hexanoate

Guidance literature:: Multi-step reaction with 3 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

With 1H-imidazole; osmium(VIII) oxide; methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; 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

: 1335000-85-5
(2R,3S,5S)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-(tosyloxy)hexanoate

Guidance literature:: Multi-step reaction with 4 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

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