(2R,3R)-3-azido-4-phenylbutane-1,2-diol

Base Information

• Chemical Name: (2R,3R)-3-azido-4-phenylbutane-1,2-diol
• CAS No.: 206361-96-8
• Molecular Formula: C₁₄H₂₂N₄O
• Molecular Weight: 262.355
• Mol file: 206361-96-8.mol

Synonyms:(2R,3R)-3-azido-4-phenylbutane-1,2-diol

Chemical Property of (2R,3R)-3-azido-4-phenylbutane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-azido-4-phenylbutane-1,2-diol

There total 10 articles about (2R,3R)-3-azido-4-phenylbutane-1,2-diol 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:

isobutylamine (78-81-9) + (2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane (136465-89-9) → (2R,3R)-3-azido-4-phenylbutane-1,2-diol (206361-96-8)

Guidance literature:

In isopropyl alcohol; at 80 ℃; for 12h;

DOI:10.1016/S0960-894X(98)00098-5

Reference yield:

ethyl 3-benzylacrylate (54966-42-6,1466-22-4) → (2R,3R)-3-azido-4-phenylbutane-1,2-diol (206361-96-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 1 h / 0 °C / Inert atmosphere

1.2: Cooling with ice

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 8 h / 0 °C

3.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 0.25 h / 70 °C / Inert atmosphere

4.1: dmap; di(n-butyl)tin oxide; triethylamine / dichloromethane / 3 h / 0 - 20 °C

5.1: potassium carbonate / methanol / 1 h / 0 - 25 °C

6.1: (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III); water / tetrahydrofuran / 14 h / 0 - 25 °C

7.1: isopropyl alcohol / 5 h / 50 °C

With titanium(IV) isopropylate; dmap; aluminum (III) chloride; lithium aluminium tetrahydride; (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III); trimethylsilylazide; water; di(n-butyl)tin oxide; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; isopropyl alcohol; benzene;

DOI:10.1016/j.tetasy.2012.06.003

Reference yield:

(2E)-4-phenylbut-2-en-1-ol (42238-15-3,22910-59-4,49676-93-9) → (2R,3R)-3-azido-4-phenylbutane-1,2-diol (206361-96-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 8 h / 0 °C

2: titanium(IV) isopropylate; trimethylsilylazide / benzene / 0.25 h / 70 °C / Inert atmosphere

3: dmap; di(n-butyl)tin oxide; triethylamine / dichloromethane / 3 h / 0 - 20 °C

4: potassium carbonate / methanol / 1 h / 0 - 25 °C

5: (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III); water / tetrahydrofuran / 14 h / 0 - 25 °C

6: isopropyl alcohol / 5 h / 50 °C

With titanium(IV) isopropylate; dmap; (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III); trimethylsilylazide; water; di(n-butyl)tin oxide; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; isopropyl alcohol; benzene;

DOI:10.1016/j.tetasy.2012.06.003

upstream raw materials:

isobutylamine

(2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane

ethyl 3-benzylacrylate

(2E)-4-phenylbut-2-en-1-ol

Downstream raw materials:

4-nitro-N-((2R(syn),3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutylbenzenesulfonamide

amprenavir

2-Methylsulfanyl-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

{(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-(2-methylsulfanyl-benzothiazole-6-sulfonyl)-amino]-propyl}-carbamic acid tert-butyl ester