3(S)-(tert-Butoxyformamido)-2(S)-hydroxy-4-phenyl-1-butanal

Base Information

• Chemical Name: 3(S)-(tert-Butoxyformamido)-2(S)-hydroxy-4-phenyl-1-butanal
• CAS No.: 152683-74-4
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.336
• Mol file: 152683-74-4.mol

Synonyms:3(S)-(tert-Butoxyformamido)-2(S)-hydroxy-4-phenyl-1-butanal

Chemical Property of 3(S)-(tert-Butoxyformamido)-2(S)-hydroxy-4-phenyl-1-butanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3(S)-(tert-Butoxyformamido)-2(S)-hydroxy-4-phenyl-1-butanal

There total 6 articles about 3(S)-(tert-Butoxyformamido)-2(S)-hydroxy-4-phenyl-1-butanal 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:

[(1S,2S)-1-Benzyl-2-hydroxy-2-(3-methyl-thiazolidin-2-yl)-ethyl]-carbamic acid tert-butyl ester → 3(S)-(tert-Butoxyformamido)-2(S)-hydroxy-4-phenyl-1-butanal (152683-74-4)

Guidance literature:

With mercury dichloride; In water; acetonitrile; for 0.25h; Yield given;

DOI:10.1021/jo00092a026

Reference yield:

Boc-L-phenylalaninal (72155-45-4) → 3(S)-(tert-Butoxyformamido)-2(S)-hydroxy-4-phenyl-1-butanal (152683-74-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 2.) Bu₄NF / 1.) THF

2: 19 percent / pyridine, 4-(dimethylamino)pyridine / 16 h / Ambient temperature

3: 13 percent / 1 M NaOH / ethanol / 0.25 h / Ambient temperature

4: 96 percent / acetonitrile / 20 h / Heating

5: NaBH₄ / methanol / 1 h / -10 °C

6: HgCl₂ / acetonitrile; H₂O / 0.25 h

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; tetrabutyl ammonium fluoride; mercury dichloride; In methanol; ethanol; water; acetonitrile;

DOI:10.1021/jo00092a026

Reference yield:

2-<2(S)-(tert-Butoxyformamido)-1-hydroxy-3-phenylpropyl>thiazole (219586-42-2) → 3(S)-(tert-Butoxyformamido)-2(S)-hydroxy-4-phenyl-1-butanal (152683-74-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 19 percent / pyridine, 4-(dimethylamino)pyridine / 16 h / Ambient temperature

2: 13 percent / 1 M NaOH / ethanol / 0.25 h / Ambient temperature

3: 96 percent / acetonitrile / 20 h / Heating

4: NaBH₄ / methanol / 1 h / -10 °C

5: HgCl₂ / acetonitrile; H₂O / 0.25 h

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; mercury dichloride; In methanol; ethanol; water; acetonitrile;

DOI:10.1021/jo00092a026

upstream raw materials:

Boc-L-phenylalaninal

2-<2(S)-(tert-Butoxyformamido)-1-hydroxy-3-phenylpropyl>thiazole

(S,S)-2-<2--1-hydroxy-3-phenylpropyl>-1,3-thiazole

Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-3-phenyl-1-thiazol-2-yl-propyl ester

Downstream raw materials:

2-<3(S)-<amino>-2(R)-hydroxy-4-phenylbutyl>-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide

2-[3(S)-[(L-asparaginyl)-amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert-butyl-decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamide

cis-N-butyldecahydro-2-<2(R)-hydroxy-4-phenyl-3(S)-aminobutyl>-(4aS,8aS)-isoquinoline-3(S)-carboxamide

Saquinavir