(2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanol

Base Information

• Chemical Name: (2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanol
• CAS No.: 197714-31-1
• Molecular Formula: C₁₅H₂₃NO₃
• Molecular Weight: 265.353
• Mol file: 197714-31-1.mol

Synonyms:(2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanol

Chemical Property of (2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanol

There total 21 articles about (2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanol 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: 81.0%

methyl (2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanoate (197714-29-7) → (2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanol (197714-31-1)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -20 ℃; for 5h;

DOI:10.1021/jo971178f

Reference yield:

(Z)-ethyl cinnamate (4610-69-9) → (2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanol (197714-31-1)

Guidance literature:

Multi-step reaction with 8 steps

2: KOH / ethanol

3: diethyl ether

4: 80 percent / KHCO₃ / dimethylformamide / 5 h / 20 °C

5: 91 percent / triethylamine; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 5 h / 0 - 20 °C

6: sodium azide / dimethylformamide / 12 h / 80 °C

7: 0.07 g / H₂ / Pd/C / ethyl acetate / 760 Torr

8: 81 percent / DIBALH / CH₂Cl₂; hexane / 5 h / -20 °C

With dmap; potassium hydroxide; sodium azide; hydrogen; diisobutylaluminium hydride; potassium hydrogencarbonate; triethylamine; palladium on activated charcoal; In diethyl ether; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: Jacobsen's epoxidation / 2: Hydrolysis / 3: Ring cleavage / 4: Esterification / 5: mesylation / 6: Substitution / 7: Catalytic hydrogenation / 8: Reduction;

DOI:10.1021/jo971178f

Reference yield:

(2S,3S)-2,3-epoxy-3-phenyl-1-propanol (104196-23-8) → (2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanol (197714-31-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium bicarbonate; sodium periodate / ruthenium trichloride trihydrate / CCl₄; acetonitrile; H₂O / 48 h

2.1: CuCN / diethyl ether; hexane / 0 °C

2.2: diethyl ether; hexane / 4 h / 0 °C

3.1: 0.18 g / KHCO₃ / dimethylformamide / 12 h / 20 °C

4.1: 93 percent / PPh₃; diethyl azodicarboxylate / benzene / 12 h / 20 °C

5.1: 0.29 g / aq. LiOH / tetrahydrofuran / 0.58 h / 70 °C

6.1: 80 percent / KHCO₃ / dimethylformamide / 5 h / 20 °C

7.1: 91 percent / triethylamine; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 5 h / 0 - 20 °C

8.1: sodium azide / dimethylformamide / 12 h / 80 °C

9.1: 0.07 g / H₂ / Pd/C / ethyl acetate / 760 Torr

10.1: 81 percent / DIBALH / CH₂Cl₂; hexane / 5 h / -20 °C

With dmap; lithium hydroxide; sodium periodate; sodium azide; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; ruthenium trichloride; palladium on activated charcoal; In tetrahydrofuran; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; benzene; 1.1: Oxidation / 2.1: transmetallation / 2.2: Ring cleavage / 3.1: Esterification / 4.1: Mitsunobu reaction / 5.1: Hydrolysis / 6.1: Esterification / 7.1: mesylation / 8.1: Substitution / 9.1: Catalytic hydrogenation / 10.1: Reduction;

DOI:10.1021/jo971178f

upstream raw materials:

methyl (2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanoate

(Z)-ethyl cinnamate

di-tert-butyl dicarbonate

(2S,3S)-2,3-epoxy-3-phenyl-1-propanol