N-[(2R,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N-isobutyl-4-methoxybenzenesulfonamide

Base Information

• Chemical Name: N-[(2R,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N-isobutyl-4-methoxybenzenesulfonamide
• CAS No.: 253265-96-2
• Molecular Formula: C₂₁H₂₈N₄O₄S
• Molecular Weight: 432.544

Synonyms:N-[(2R,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N-isobutyl-4-methoxybenzenesulfonamide

Chemical Property of N-[(2R,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N-isobutyl-4-methoxybenzenesulfonamide

Chemical Property:

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Technology Process of N-[(2R,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N-isobutyl-4-methoxybenzenesulfonamide

There total 2 articles about N-[(2R,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N-isobutyl-4-methoxybenzenesulfonamide 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:

4-methoxy-phenyl-sulphonyl chloride (98-68-0) + (2R,3R)-3-azido-4-phenylbutane-1,2-diol (206361-96-8) → N-[(2R,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N-isobutyl-4-methoxybenzenesulfonamide (253265-96-2)

Guidance literature:

With sodium hydrogencarbonate;

DOI:10.1016/S0960-894X(98)00098-5

Reference yield:

(2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane (136465-89-9) → N-[(2R,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N-isobutyl-4-methoxybenzenesulfonamide (253265-96-2)

Guidance literature:

Multi-step reaction with 2 steps

1: propan-2-ol / 12 h / 80 °C

2: aq. NaHCO₃

With sodium hydrogencarbonate; In isopropyl alcohol;

DOI:10.1016/S0960-894X(98)00098-5

Reference yield: 68.0%

(1S,2R)-(2-hydroxy-indan-1-yl)carbamic acid prop-2-ynyl ester + N-[(2R,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N-isobutyl-4-methoxybenzenesulfonamide (253265-96-2) → (1-(3-hydroxy-4-(N-isobutyl-4-methoxyphenylsulfonamido)-1-phenylbutan-2-yl)-1H-1,2,3-triazol-4-yl)methyl-2-hydroxy-2,3-dihydro-1H-inden-1-ylcarbamate

Guidance literature:

With copper; copper(II) sulfate; In methanol; for 48h;

DOI:10.1002/anie.200502161

upstream raw materials:

4-methoxy-phenyl-sulphonyl chloride

(2R,3R)-3-azido-4-phenylbutane-1,2-diol

(2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane

Downstream raw materials:

N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-methoxybenzenesulfonamide

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