tert-butyl (2S,3S,4R)-3-hydroxy-5,5-dimethoxy-4-nitro-1-phenylpentan-2-ylcarbamate

Base Information

• Chemical Name: tert-butyl (2S,3S,4R)-3-hydroxy-5,5-dimethoxy-4-nitro-1-phenylpentan-2-ylcarbamate
• CAS No.: 1029289-09-5
• Molecular Formula: C₁₈H₂₈N₂O₇
• Molecular Weight: 384.43
• Mol file: 1029289-09-5.mol

Synonyms:tert-butyl (2S,3S,4R)-3-hydroxy-5,5-dimethoxy-4-nitro-1-phenylpentan-2-ylcarbamate

Chemical Property of tert-butyl (2S,3S,4R)-3-hydroxy-5,5-dimethoxy-4-nitro-1-phenylpentan-2-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of tert-butyl (2S,3S,4R)-3-hydroxy-5,5-dimethoxy-4-nitro-1-phenylpentan-2-ylcarbamate

There total 2 articles about tert-butyl (2S,3S,4R)-3-hydroxy-5,5-dimethoxy-4-nitro-1-phenylpentan-2-ylcarbamate 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: 97.0%

2-nitroacetaldehyde dimethyl acetal (69425-53-2) + Boc-L-phenylalaninal (72155-45-4) → tert-butyl (2S,3S,4R)-3-hydroxy-5,5-dimethoxy-4-nitro-1-phenylpentan-2-ylcarbamate (1029289-09-5)

Guidance literature:

2-nitroacetaldehyde dimethyl acetal; Boc-L-phenylalaninal; With (S)-La-Li₃-(binaphthoxide)3; In tetrahydrofuran; at -50 - -20 ℃; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol800653d

Reference yield: 87.0%

2-nitroacetaldehyde dimethyl acetal (69425-53-2) + Boc-L-phenylalaninal (72155-45-4) → tert-butyl (2S)-3-hydroxy-5,5-dimethoxy-4-nitro-1-phenylpentan-2-ylcarbamate + tert-butyl (2S,3S,4R)-3-hydroxy-5,5-dimethoxy-4-nitro-1-phenylpentan-2-ylcarbamate (1029289-09-5) + tert-butyl (2S,3R,4S)-3-hydroxy-5,5-dimethoxy-4-nitro-1-phenylpentan-2-ylcarbamate (1029289-50-6)

Guidance literature:

2-nitroacetaldehyde dimethyl acetal; With C₂₆H₂₂BrLaN₂O₅Pd; In tetrahydrofuran; at -30 ℃; for 1h; Inert atmosphere;

Boc-L-phenylalaninal; In tetrahydrofuran; xylenes; at -30 ℃; for 72h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol800653d

Reference yield:

tert-butyl (2S,3S,4R)-3-hydroxy-5,5-dimethoxy-4-nitro-1-phenylpentan-2-ylcarbamate (1029289-09-5) → C18H30N2O5

Guidance literature:

With sodium tetrahydroborate; nickel(II) chloride hexahydrate; In methanol; Inert atmosphere;

DOI:10.1021/ol800653d

upstream raw materials:

2-nitroacetaldehyde dimethyl acetal

Boc-L-phenylalaninal

Refernces