(4R,5S)-tert-butyl 5-azido-4-(4'-methyl-phenylsulfonyloxy)-5-phenyl-pentanoate

Base Information

Chemical Name:(4R,5S)-tert-butyl 5-azido-4-(4'-methyl-phenylsulfonyloxy)-5-phenyl-pentanoate
CAS No.:910870-31-4
Molecular Formula:C₂₂H₂₇N₃O₅S
Molecular Weight:445.539
Hs Code.:

Synonyms:(4R,5S)-tert-butyl 5-azido-4-(4'-methyl-phenylsulfonyloxy)-5-phenyl-pentanoate

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Chemical Property of (4R,5S)-tert-butyl 5-azido-4-(4'-methyl-phenylsulfonyloxy)-5-phenyl-pentanoate

Chemical Property:

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Technology Process of (4R,5S)-tert-butyl 5-azido-4-(4'-methyl-phenylsulfonyloxy)-5-phenyl-pentanoate

There total 5 articles about (4R,5S)-tert-butyl 5-azido-4-(4'-methyl-phenylsulfonyloxy)-5-phenyl-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: 73.0%

: 910870-25-6
(4R,5S)-tert-butyl 5-azido-4-hydroxy-5-phenyl-pentanoate

: 98-59-9
p-toluenesulfonyl chloride

: 910870-31-4
(4R,5S)-tert-butyl 5-azido-4-(4'-methyl-phenylsulfonyloxy)-5-phenyl-pentanoate

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 48h;
DOI:10.1039/b606879k

Reference yield:

: 910869-99-7
(E)-tert-butyl 5-phenyl-pent-4-enoate

: 910870-31-4
(4R,5S)-tert-butyl 5-azido-4-(4'-methyl-phenylsulfonyloxy)-5-phenyl-pentanoate

Guidance literature:: Multi-step reaction with 4 steps

1: K₂OsO₄*2H₂O; K₃Fe(CN)6; K₂CO₃ / MeSO₂NH₂; (DHQD)2PHAL / 2-methyl-propan-2-ol; H₂O / 96 h / 3 °C

2: 85 percent / SOCl₂; pyridine / CH₂Cl₂ / 4 h / 20 °C

3: 0.53 g / NaN₃ / dimethylformamide / 48 h / 60 °C

4: 73 percent / Et₃N; DMAP / CH₂Cl₂ / 48 h

With pyridine; dmap; potassium osmate(VI); thionyl chloride; sodium azide; potassium carbonate; triethylamine; potassium hexacyanoferrate(III); methanesulfonamide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1039/b606879k

Reference yield:

: 4392-24-9
Cinnamyl bromide

: 910870-31-4
(4R,5S)-tert-butyl 5-azido-4-(4'-methyl-phenylsulfonyloxy)-5-phenyl-pentanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

1.2: HMPA / tetrahydrofuran / 0.5 h / -78 °C

1.3: 96 percent / tetrahydrofuran / 4 h / -78 °C

2.1: K₂OsO₄*2H₂O; K₃Fe(CN)6; K₂CO₃ / MeSO₂NH₂; (DHQD)2PHAL / 2-methyl-propan-2-ol; H₂O / 96 h / 3 °C

3.1: 85 percent / SOCl₂; pyridine / CH₂Cl₂ / 4 h / 20 °C

4.1: 0.53 g / NaN₃ / dimethylformamide / 48 h / 60 °C

5.1: 73 percent / Et₃N; DMAP / CH₂Cl₂ / 48 h

With pyridine; dmap; potassium osmate(VI); thionyl chloride; sodium azide; potassium carbonate; triethylamine; potassium hexacyanoferrate(III); lithium diisopropyl amide; methanesulfonamide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1039/b606879k