C₅₄H₆₆FN₅O₁₆Si

Base Information

• Chemical Name: C₅₄H₆₆FN₅O₁₆Si
• CAS No.: 331731-43-2
• Molecular Formula: C₅₄H₆₆FN₅O₁₆Si
• Molecular Weight: 1088.23
• Mol file: 331731-43-2.mol

Synonyms:C₅₄H₆₆FN₅O₁₆Si

Chemical Property of C₅₄H₆₆FN₅O₁₆Si

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₅₄H₆₆FN₅O₁₆Si

There total 27 articles about C₅₄H₆₆FN₅O₁₆Si 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: 78.0%

5-((R)-1-Amino-2-hydroxy-ethyl)-2-methoxy-benzene-1,3-diol (219911-58-7) + (S)-{3-[5-((R)-2-Benzyloxy-1-tert-butoxycarbonylamino-ethyl)-2-methoxy-phenoxy]-5-methoxy-phenyl}-[(R)-3-(4-fluoro-3-nitro-phenyl)-2-(2-trimethylsilanyl-ethoxycarbonylamino)-propionylamino]-acetic acid (296252-57-8) → C54H66FN5O16Si (331731-43-2)

Guidance literature:

With 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In tetrahydrofuran; at 0 ℃; for 4.5h;

DOI:10.1021/ja003835i

Reference yield:

3-hydroxy-5-methoxybenzaldehyde (57179-35-8) → C54H66FN5O16Si (331731-43-2)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 89 percent / K₂CO₃ / dimethylformamide / 3 h / 60 °C

2.1: 87 percent / tetrahydrofuran / 2 h / -78 - 25 °C

3.1: 78 percent / t-butyl hypochlorite; (DHQD)2PHAL; NaOH / K₂OsO₂(OH)4 / H₂O; propan-1-ol / 1 h / 25 °C

4.1: 95 percent / i-Pr₂NEt / CH₂Cl₂ / 20 h / 25 °C

5.1: H₂ / Pd/C / methanol / 3 h

6.1: 3.01 g / pyridine / CH₂Cl₂ / 3 h / 25 °C

7.1: 70 percent / K₂CO₃; 18-crown-6 / dimethylsulfoxide / 15 h / 25 °C

8.1: 100 percent / H₂ / Pd/C / methanol / 1 h

9.1: t-BuONO; HBF₄ / acetonitrile; H₂O / 0.33 h

9.2: 80 percent / Cu₂O; Cu(NO₃)2 / acetonitrile; H₂O / 1 h / 0 °C

10.1: 95 percent / K₂CO₃; Bu₄NI / dimethylformamide / 25 °C

11.1: 91 percent / NaH; Bu₄NI / dimethylformamide; tetrahydrofuran / 2 h / 0 °C

12.1: aq. HCl / ethyl acetate / 0.33 h / 0 °C

13.1: 0.341 g / NaHCO₃ / tetrahydrofuran; H₂O / 18 h

14.1: 96 percent / K₂CO₃; H₂O / methanol / 18 h / 25 °C

15.1: 89 percent / EDCI*HCl; HOBt; DMF / 18 h / 0 °C

16.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 25 °C

17.1: 63.0 mg / NaClO₂; NaH₂PO₄*2H₂O; resorcinol / dimethylsulfoxide; H₂O / 1.5 h

18.1: 78 percent / DEPBT / tetrahydrofuran / 4.5 h / 0 °C

With pyridine; hydrogenchloride; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; tetrafluoroboric acid; tert.-butylnitrite; 18-crown-6 ether; tert-butylhypochlorite; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1,4-bis(9-O-dihydroquinidine)phthalazine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; recorcinol; palladium on activated charcoal; potassium dioxotetrahydroxoosmate(VI); In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 3.1: Sharpless asymmetric aminohydroxylation;

DOI:10.1021/ja003835i

Reference yield:

3-(benzyloxy)-5-methoxybenzaldehyde (50637-29-1) → C54H66FN5O16Si (331731-43-2)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 87 percent / tetrahydrofuran / 2 h / -78 - 25 °C

2.1: 78 percent / t-butyl hypochlorite; (DHQD)2PHAL; NaOH / K₂OsO₂(OH)4 / H₂O; propan-1-ol / 1 h / 25 °C

3.1: 95 percent / i-Pr₂NEt / CH₂Cl₂ / 20 h / 25 °C

4.1: H₂ / Pd/C / methanol / 3 h

5.1: 3.01 g / pyridine / CH₂Cl₂ / 3 h / 25 °C

6.1: 70 percent / K₂CO₃; 18-crown-6 / dimethylsulfoxide / 15 h / 25 °C

7.1: 100 percent / H₂ / Pd/C / methanol / 1 h

8.1: t-BuONO; HBF₄ / acetonitrile; H₂O / 0.33 h

8.2: 80 percent / Cu₂O; Cu(NO₃)2 / acetonitrile; H₂O / 1 h / 0 °C

9.1: 95 percent / K₂CO₃; Bu₄NI / dimethylformamide / 25 °C

10.1: 91 percent / NaH; Bu₄NI / dimethylformamide; tetrahydrofuran / 2 h / 0 °C

11.1: aq. HCl / ethyl acetate / 0.33 h / 0 °C

12.1: 0.341 g / NaHCO₃ / tetrahydrofuran; H₂O / 18 h

13.1: 96 percent / K₂CO₃; H₂O / methanol / 18 h / 25 °C

14.1: 89 percent / EDCI*HCl; HOBt; DMF / 18 h / 0 °C

15.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 25 °C

16.1: 63.0 mg / NaClO₂; NaH₂PO₄*2H₂O; resorcinol / dimethylsulfoxide; H₂O / 1.5 h

17.1: 78 percent / DEPBT / tetrahydrofuran / 4.5 h / 0 °C

With pyridine; hydrogenchloride; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; tetrafluoroboric acid; tert.-butylnitrite; 18-crown-6 ether; tert-butylhypochlorite; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1,4-bis(9-O-dihydroquinidine)phthalazine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; recorcinol; palladium on activated charcoal; potassium dioxotetrahydroxoosmate(VI); In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 2.1: Sharpless asymmetric aminohydroxylation;

DOI:10.1021/ja003835i

upstream raw materials:

5-((R)-1-Amino-2-hydroxy-ethyl)-2-methoxy-benzene-1,3-diol

(S)-{3-[5-((R)-2-Benzyloxy-1-tert-butoxycarbonylamino-ethyl)-2-methoxy-phenoxy]-5-methoxy-phenyl}-[(R)-3-(4-fluoro-3-nitro-phenyl)-2-(2-trimethylsilanyl-ethoxycarbonylamino)-propionylamino]-acetic acid

di-tert-butyl dicarbonate

3-hydroxy-5-methoxybenzaldehyde

Refernces