(R)-3-(4-Benzyloxy-phenyl)-2-({2-[(2S,4S,6R,7S,9S)-7-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-2,4,6,10-tetramethyl-undecanoylamino]-acetyl}-methyl-amino)-propionic acid

Base Information

• Chemical Name: (R)-3-(4-Benzyloxy-phenyl)-2-({2-[(2S,4S,6R,7S,9S)-7-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-2,4,6,10-tetramethyl-undecanoylamino]-acetyl}-methyl-amino)-propionic acid
• CAS No.: 160531-28-2
• Molecular Formula: C₄₀H₆₄N₂O₇Si
• Molecular Weight: 713.043
• Mol file: 160531-28-2.mol

Synonyms:(R)-3-(4-Benzyloxy-phenyl)-2-({2-[(2S,4S,6R,7S,9S)-7-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-2,4,6,10-tetramethyl-undecanoylamino]-acetyl}-methyl-amino)-propionic acid

Chemical Property of (R)-3-(4-Benzyloxy-phenyl)-2-({2-[(2S,4S,6R,7S,9S)-7-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-2,4,6,10-tetramethyl-undecanoylamino]-acetyl}-methyl-amino)-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-(4-Benzyloxy-phenyl)-2-({2-[(2S,4S,6R,7S,9S)-7-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-2,4,6,10-tetramethyl-undecanoylamino]-acetyl}-methyl-amino)-propionic acid

There total 26 articles about (R)-3-(4-Benzyloxy-phenyl)-2-({2-[(2S,4S,6R,7S,9S)-7-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-2,4,6,10-tetramethyl-undecanoylamino]-acetyl}-methyl-amino)-propionic 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: 96.0%

(R)-3-(4-Benzyloxy-phenyl)-2-({2-[(2S,4S,6R,7S,9S)-7-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-2,4,6,10-tetramethyl-undecanoylamino]-acetyl}-methyl-amino)-propionic acid methyl ester → (R)-3-(4-Benzyloxy-phenyl)-2-({2-[(2S,4S,6R,7S,9S)-7-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-2,4,6,10-tetramethyl-undecanoylamino]-acetyl}-methyl-amino)-propionic acid (160531-28-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81206-0

Reference yield:

4-methylpent-2-en-1-ol (5362-55-0) → (R)-3-(4-Benzyloxy-phenyl)-2-({2-[(2S,4S,6R,7S,9S)-7-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-2,4,6,10-tetramethyl-undecanoylamino]-acetyl}-methyl-amino)-propionic acid (160531-28-2)

Guidance literature:

Multi-step reaction with 26 steps

1: 2.) Red-Al / 1.) Sharpless epoxidation

2: 96 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 13 h / Ambient temperature

3: 1.) 60percent NaH, 2.) concd HCl / 1.) DMF, 0 deg C to room temp., 2.5 h, 2.) MeOH, THF, 30 deg C, 4 h

4: 96 percent / (COCl)2, DMSO; Et₃N / CH₂Cl₂ / -78 deg C, 20 min; -78 to 0 deg C, 0 deg C, 15 min

5: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 50 min; -78 deg C, 30 min; 0 deg C, 1 h

6: 92 percent / Me₃Al / tetrahydrofuran; toluene / -19 deg C, 2 h; -6 deg C, 2 h;

7: 96 percent / i-Pr₂NEt / 2 h / Ambient temperature

8: 91 percent / 1.0 M DIBAL / tetrahydrofuran; hexane / 0.17 h / -78 °C

9: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; -78 deg C, 30 min; 0 deg C, 1 h

10: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1.5 h, 2.) CHCl₃, Et₂O

11: 93 percent / tetrahydrofuran / 10 h / 70 °C

12: 79 percent / Bu₃SnH / toluene / 0.22 h / Heating

13: 97 percent / 1.0 M LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

14: 98 percent / DMSO, (COCl)2; Et₃N / CH₂Cl₂ / -78 °C / -78 deg C, 10 min; -78 to 0 deg C, 0 deg C, 10 min

15: 88 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; -78 deg C, 30 min; 0 deg C, 1 h

16: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1 h, 2.) CHCl₃, Et₂O

17: 94 percent / tetrahydrofuran / 5 h / 70 °C

18: 76 percent / Bu₃SnH / toluene / 0.17 h / Heating

19: 96 percent / concd HCl / methanol / 2 h / 50 °C

20: Ph₃P, 1.0 M (EtOOCN)2, p-nitrobenzoic acid / diethyl ether / 17.5 h / Ambient temperature

21: 52.0 mg / 20percent (w/w) aq. NaOH / methanol / 2 h / 45 °C

22: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

23: K₂CO₃ / CH₂Cl₂; methanol; tetrahydrofuran; H₂O / 1 h / 40 °C

24: 2.2 mg / H₂, K₂CO₃ / 10percent Pd/C / methanol / 1 h / 760 Torr / Ambient temperature

25: 0.33 M DEPC, Et₃N / dimethylformamide / 0.83 h / 0 °C

26: 96 percent / LiOH*H₂O / H₂O; tetrahydrofuran / 1 h / Ambient temperature

With hydrogenchloride; dmap; lithium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; dihydrogen peroxide; trimethylaluminum; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; diethyl dicarbonate; diethylazodicarboxylate; 4-nitro-benzoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)81206-0

Reference yield:

(S)-4-methyl-pentane-1,3-diol (16451-50-6) → (R)-3-(4-Benzyloxy-phenyl)-2-({2-[(2S,4S,6R,7S,9S)-7-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-2,4,6,10-tetramethyl-undecanoylamino]-acetyl}-methyl-amino)-propionic acid (160531-28-2)

Guidance literature:

Multi-step reaction with 25 steps

1: 96 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 13 h / Ambient temperature

2: 1.) 60percent NaH, 2.) concd HCl / 1.) DMF, 0 deg C to room temp., 2.5 h, 2.) MeOH, THF, 30 deg C, 4 h

3: 96 percent / (COCl)2, DMSO; Et₃N / CH₂Cl₂ / -78 deg C, 20 min; -78 to 0 deg C, 0 deg C, 15 min

4: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 50 min; -78 deg C, 30 min; 0 deg C, 1 h

5: 92 percent / Me₃Al / tetrahydrofuran; toluene / -19 deg C, 2 h; -6 deg C, 2 h;

6: 96 percent / i-Pr₂NEt / 2 h / Ambient temperature

7: 91 percent / 1.0 M DIBAL / tetrahydrofuran; hexane / 0.17 h / -78 °C

8: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; -78 deg C, 30 min; 0 deg C, 1 h

9: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1.5 h, 2.) CHCl₃, Et₂O

10: 93 percent / tetrahydrofuran / 10 h / 70 °C

11: 79 percent / Bu₃SnH / toluene / 0.22 h / Heating

12: 97 percent / 1.0 M LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

13: 98 percent / DMSO, (COCl)2; Et₃N / CH₂Cl₂ / -78 °C / -78 deg C, 10 min; -78 to 0 deg C, 0 deg C, 10 min

14: 88 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; -78 deg C, 30 min; 0 deg C, 1 h

15: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1 h, 2.) CHCl₃, Et₂O

16: 94 percent / tetrahydrofuran / 5 h / 70 °C

17: 76 percent / Bu₃SnH / toluene / 0.17 h / Heating

18: 96 percent / concd HCl / methanol / 2 h / 50 °C

19: Ph₃P, 1.0 M (EtOOCN)2, p-nitrobenzoic acid / diethyl ether / 17.5 h / Ambient temperature

20: 52.0 mg / 20percent (w/w) aq. NaOH / methanol / 2 h / 45 °C

21: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

22: K₂CO₃ / CH₂Cl₂; methanol; tetrahydrofuran; H₂O / 1 h / 40 °C

23: 2.2 mg / H₂, K₂CO₃ / 10percent Pd/C / methanol / 1 h / 760 Torr / Ambient temperature

24: 0.33 M DEPC, Et₃N / dimethylformamide / 0.83 h / 0 °C

25: 96 percent / LiOH*H₂O / H₂O; tetrahydrofuran / 1 h / Ambient temperature

With hydrogenchloride; dmap; lithium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; dihydrogen peroxide; trimethylaluminum; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethyl dicarbonate; diethylazodicarboxylate; 4-nitro-benzoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)81206-0

upstream raw materials:

4-methylpent-2-en-1-ol

(S)-4-methyl-pentane-1,3-diol

(S)-3-(benzyloxy)-4-methylpentanal

(S)-3-Benzyloxy-4-methyl-pentan-1-ol