(2S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethyl-silanyloxy)-pentanoic acid benzyl ester

Base Information

• Chemical Name: (2S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethyl-silanyloxy)-pentanoic acid benzyl ester
• CAS No.: 817166-98-6
• Molecular Formula: C₂₃H₃₉NO₅Si
• Molecular Weight: 437.652

Synonyms:(2S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethyl-silanyloxy)-pentanoic acid benzyl ester

Chemical Property of (2S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethyl-silanyloxy)-pentanoic acid benzyl ester

Chemical Property:

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Technology Process of (2S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethyl-silanyloxy)-pentanoic acid benzyl ester

There total 3 articles about (2S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethyl-silanyloxy)-pentanoic acid benzyl ester 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: 95.0%

(S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester (91229-97-9) + tert-butyldimethylsilyl chloride (18162-48-6) → (2S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethyl-silanyloxy)-pentanoic acid benzyl ester (817166-98-6)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 - 20 ℃;

DOI:10.1039/c0cc02889d

Reference yield:

Boc-Glu-OBn (30924-93-7) → (2S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethyl-silanyloxy)-pentanoic acid benzyl ester (817166-98-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 4-methylmorpholine; isobutyl chloroformate / tetrahydrofuran / 0.17 h / -15 °C

1.2: 98.6 percent / NaBH₄ / tetrahydrofuran; methanol / 0.17 h / -15 °C

2.1: 72.7 percent / Et₃N; 4-DMAP / CH₂Cl₂

With 4-methyl-morpholine; dmap; triethylamine; isobutyl chloroformate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2005.08.029

Reference yield:

Boc-Glu(OSu)-OBn (78658-49-8) → (2S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethyl-silanyloxy)-pentanoic acid benzyl ester (817166-98-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄; H₂O / tetrahydrofuran / 2 h / 0 °C

2: 8.48 g / imidazole / dimethylformamide / 20 °C

With 1H-imidazole; sodium tetrahydroborate; water; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ol047879y

upstream raw materials:

(S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester

tert-butyldimethylsilyl chloride

Boc-Glu-OBn

Boc-Glu(OSu)-OBn

Downstream raw materials:

(2S)-N'-(2-tert-butoxycarbonylamino-5-hydroxy-pentanoyl)-N-methyl-hydrazinecarboxylic acid benzyl ester

(2S)-N'-[2-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-pentanoyl]-N-methyl-hydrazinecarboxylic acid benzyl ester

[(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-hydroxybutyl]carbamic acid tert-butyl ester

(4S)-4-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-4-[bis(tert-butoxycarbonyl)amino]butyric acid

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