(2R,3S)-benzyl 5-(tert-butoxycarbonylamino)-3-hydroxy-2-[(4-methylphenyl)sulfonyloxy]pentanoate

Base Information

Chemical Name:(2R,3S)-benzyl 5-(tert-butoxycarbonylamino)-3-hydroxy-2-[(4-methylphenyl)sulfonyloxy]pentanoate
CAS No.:1175033-04-1
Molecular Formula:C₂₄H₃₁NO₈S
Molecular Weight:493.578
Hs Code.:

Synonyms:(2R,3S)-benzyl 5-(tert-butoxycarbonylamino)-3-hydroxy-2-[(4-methylphenyl)sulfonyloxy]pentanoate

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Chemical Property of (2R,3S)-benzyl 5-(tert-butoxycarbonylamino)-3-hydroxy-2-[(4-methylphenyl)sulfonyloxy]pentanoate

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Technology Process of (2R,3S)-benzyl 5-(tert-butoxycarbonylamino)-3-hydroxy-2-[(4-methylphenyl)sulfonyloxy]pentanoate

There total 3 articles about (2R,3S)-benzyl 5-(tert-butoxycarbonylamino)-3-hydroxy-2-[(4-methylphenyl)sulfonyloxy]pentanoate 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: 65.0%

: 1175033-05-2
benzyl (2R,3S)-5-[(tert-butoxycarbonyl)amino]-2,3-dihydroxypentanoate

: 98-59-9
p-toluenesulfonyl chloride

: 1175033-04-1
(2R,3S)-benzyl 5-(tert-butoxycarbonylamino)-3-hydroxy-2-[(4-methylphenyl)sulfonyloxy]pentanoate

Guidance literature:: With triethylamine; In dichloromethane; at 5 ℃; for 72h; regioselective reaction;
DOI:10.1021/jo901143b

Reference yield: 55.0%

: 1175033-05-2
benzyl (2R,3S)-5-[(tert-butoxycarbonyl)amino]-2,3-dihydroxypentanoate

: 98-59-9
p-toluenesulfonyl chloride

: 1175033-04-1
(2R,3S)-benzyl 5-(tert-butoxycarbonylamino)-3-hydroxy-2-[(4-methylphenyl)sulfonyloxy]pentanoate

: 1353654-95-1
C₂₄H₂₉NO₇S

Guidance literature:: With 1,4-diaza-bicyclo[2.2.2]octane; In dichloromethane; at -10 ℃; Inert atmosphere;
DOI:10.1016/j.tet.2011.10.099

Reference yield:

: 1175033-06-3
benzyl (2E)-5-[(tert-butoxycarbonyl)amino]pent-2-enoate

: 1175033-04-1
(2R,3S)-benzyl 5-(tert-butoxycarbonylamino)-3-hydroxy-2-[(4-methylphenyl)sulfonyloxy]pentanoate

: 1353654-95-1
C₂₄H₂₉NO₇S

Guidance literature:: Multi-step reaction with 2 steps

1: AD-mix-α; methanesulfonamide; water / tert-butyl alcohol / 24 h / 0 °C / Inert atmosphere

2: 1,4-diaza-bicyclo[2.2.2]octane / dichloromethane / -10 °C / Inert atmosphere

With 1,4-diaza-bicyclo[2.2.2]octane; methanesulfonamide; AD-mix-α; water; In dichloromethane; tert-butyl alcohol;
DOI:10.1016/j.tet.2011.10.099