(2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-7-(2,4,6-trimethoxybenzylcarbamoyl)heptanoic acid

Base Information

• Chemical Name: (2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-7-(2,4,6-trimethoxybenzylcarbamoyl)heptanoic acid
• CAS No.: 817166-93-1
• Molecular Formula: C₃₆H₅₆N₂O₉Si
• Molecular Weight: 688.934
• Mol file: 817166-93-1.mol

Synonyms:(2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-7-(2,4,6-trimethoxybenzylcarbamoyl)heptanoic acid

Chemical Property of (2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-7-(2,4,6-trimethoxybenzylcarbamoyl)heptanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-7-(2,4,6-trimethoxybenzylcarbamoyl)heptanoic acid

There total 18 articles about (2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-7-(2,4,6-trimethoxybenzylcarbamoyl)heptanoic acid 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-(tert-butyldimethylsilanyloxy)-(1S)-1-(5-oxotetrahydrofuran-(2R)-2-yl)butyl]carbamic acid tert-butyl ester (817166-96-4) → (2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-7-(2,4,6-trimethoxybenzylcarbamoyl)heptanoic acid (817166-93-1)

Guidance literature:

Multi-step reaction with 9 steps

1: LDA / tetrahydrofuran; hexane / 3.5 h / -78 °C

2: Ac₂O; Et₃N / 1.25 h / Heating

3: 0.790 g / H₂ / Pd/C / ethyl acetate; methanol / 4.25 h

4: 92 percent / DMAP / tetrahydrofuran / 21 h / Heating

5: 78 percent / CrO₃; H₂SO₄ / acetone / 1.5 h / -10 °C

6: 92 percent / 1-HOBt; diisopropylethylamine; HBTU / dimethylformamide / 0 - 20 °C

7: 95 percent / LiBr / acetonitrile / 65 °C

8: aq. LiOH / dioxane / 1 h / 20 °C

9: 0.284 g / imidazole / dimethylformamide / 44 h / 20 °C

With 1H-imidazole; chromium(VI) oxide; dmap; lithium hydroxide; sulfuric acid; hydrogen; acetic anhydride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium bromide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; 5: Jones oxidation;

DOI:10.1021/ol047879y

Reference yield:

5-tert-butoxycarbonylamino-8-(tert-butyl-dimethyl-silanyloxy)-4-oxo-oct-2-enoic acid methyl ester → (2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-7-(2,4,6-trimethoxybenzylcarbamoyl)heptanoic acid (817166-93-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.44 g / H₂ / Pd/C / ethyl acetate / 4 h

2: LiAlH(t-BuO)3 / ethanol / 2.5 h / -78 °C

3: 2.909 g / AcOH / toluene / 3 h / Heating

4: LDA / tetrahydrofuran; hexane / 3.5 h / -78 °C

5: Ac₂O; Et₃N / 1.25 h / Heating

6: 0.790 g / H₂ / Pd/C / ethyl acetate; methanol / 4.25 h

7: 92 percent / DMAP / tetrahydrofuran / 21 h / Heating

8: 78 percent / CrO₃; H₂SO₄ / acetone / 1.5 h / -10 °C

9: 92 percent / 1-HOBt; diisopropylethylamine; HBTU / dimethylformamide / 0 - 20 °C

10: 95 percent / LiBr / acetonitrile / 65 °C

11: aq. LiOH / dioxane / 1 h / 20 °C

12: 0.284 g / imidazole / dimethylformamide / 44 h / 20 °C

With 1H-imidazole; chromium(VI) oxide; dmap; lithium hydroxide; sulfuric acid; hydrogen; acetic anhydride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; lithium tri-t-butoxyaluminum hydride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium bromide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 8: Jones oxidation;

DOI:10.1021/ol047879y

Reference yield:

(2S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethyl-silanyloxy)-pentanoic acid benzyl ester (817166-98-6) → (2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-7-(2,4,6-trimethoxybenzylcarbamoyl)heptanoic acid (817166-93-1)

Guidance literature:

Multi-step reaction with 14 steps

1: 92 percent / tetrahydrofuran; hexane / 4 h / -78 °C

2: NaH / tetrahydrofuran / -78 - -30 °C

3: 1.44 g / H₂ / Pd/C / ethyl acetate / 4 h

4: LiAlH(t-BuO)3 / ethanol / 2.5 h / -78 °C

5: 2.909 g / AcOH / toluene / 3 h / Heating

6: LDA / tetrahydrofuran; hexane / 3.5 h / -78 °C

7: Ac₂O; Et₃N / 1.25 h / Heating

8: 0.790 g / H₂ / Pd/C / ethyl acetate; methanol / 4.25 h

9: 92 percent / DMAP / tetrahydrofuran / 21 h / Heating

10: 78 percent / CrO₃; H₂SO₄ / acetone / 1.5 h / -10 °C

11: 92 percent / 1-HOBt; diisopropylethylamine; HBTU / dimethylformamide / 0 - 20 °C

12: 95 percent / LiBr / acetonitrile / 65 °C

13: aq. LiOH / dioxane / 1 h / 20 °C

14: 0.284 g / imidazole / dimethylformamide / 44 h / 20 °C

With 1H-imidazole; chromium(VI) oxide; dmap; lithium hydroxide; sulfuric acid; hydrogen; acetic anhydride; sodium hydride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; lithium tri-t-butoxyaluminum hydride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium bromide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 2: Horner-Wadsworth-Emmons reaction / 10: Jones oxidation;

DOI:10.1021/ol047879y

upstream raw materials:

tert-butyldimethylsilyl chloride

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

5-tert-butoxycarbonylamino-8-(tert-butyldimethylsilanyloxy)-4-oxooctanoic acid methyl ester

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