(2S,3S)-N¹-amino-2,3-bis(benzyloxymethyl)azetidine

Base Information

• Chemical Name: (2S,3S)-N¹-amino-2,3-bis(benzyloxymethyl)azetidine
• CAS No.: 159721-87-6
• Molecular Formula: C₁₉H₂₄N₂O₂
• Molecular Weight: 312.412
• Mol file: 159721-87-6.mol

Synonyms:(2S,3S)-N¹-amino-2,3-bis(benzyloxymethyl)azetidine

Chemical Property of (2S,3S)-N¹-amino-2,3-bis(benzyloxymethyl)azetidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-N¹-amino-2,3-bis(benzyloxymethyl)azetidine

There total 10 articles about (2S,3S)-N¹-amino-2,3-bis(benzyloxymethyl)azetidine 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: 83.0%

(2S,3S)-N1-nitroso-2,3-bis(benzyloxymethyl)azetidine (159721-86-5) → (2S,3S)-N1-amino-2,3-bis(benzyloxymethyl)azetidine (159721-87-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -10 ℃; for 3.5h;

DOI:10.1016/S0040-4020(01)89342-X

Reference yield:

(S,S)-1,4-bis(benzyloxy)-2,3-epoxybutane (81177-24-4) → (2S,3S)-N1-amino-2,3-bis(benzyloxymethyl)azetidine (159721-87-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 94 percent / copper(I) iodide / diethyl ether; tetrahydrofuran / 4.5 h / -10 °C

2: 93 percent / triethylamine / CH₂Cl₂ / 4 h / 0 °C

3: 90 percent / sodium azide / dimethylformamide / 1 h / 98 - 105 °C

4: 1.) ozone; 2.) NaBH₄ / 1.) methanol, -20 deg C, 3 h; 2.) rt., 10 h

5: 98 percent / triethylamine / CH₂Cl₂ / 4 h / 0 °C

6: 92 percent / hydrogen / Raney-nickel (W-2) / ethanol / 15 h / Ambient temperature

7: 100 percent / isoamyl nitrite / tetrahydrofuran / 20 h / Ambient temperature

8: 83 percent / lithium aluminum hydride / tetrahydrofuran / 3.5 h / -10 °C

With sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; sodium azide; hydrogen; ozone; triethylamine; isopentyl nitrite; Raney-Nickel (W-2); In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)89342-X

Reference yield:

(2R,3R)-2-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-4-penten-2-ol (113368-83-5) → (2S,3S)-N1-amino-2,3-bis(benzyloxymethyl)azetidine (159721-87-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / triethylamine / CH₂Cl₂ / 4 h / 0 °C

2: 90 percent / sodium azide / dimethylformamide / 1 h / 98 - 105 °C

3: 1.) ozone; 2.) NaBH₄ / 1.) methanol, -20 deg C, 3 h; 2.) rt., 10 h

4: 98 percent / triethylamine / CH₂Cl₂ / 4 h / 0 °C

5: 92 percent / hydrogen / Raney-nickel (W-2) / ethanol / 15 h / Ambient temperature

6: 100 percent / isoamyl nitrite / tetrahydrofuran / 20 h / Ambient temperature

7: 83 percent / lithium aluminum hydride / tetrahydrofuran / 3.5 h / -10 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; hydrogen; ozone; triethylamine; isopentyl nitrite; Raney-Nickel (W-2); In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)89342-X

upstream raw materials:

(2S,3S)-N¹-nitroso-2,3-bis(benzyloxymethyl)azetidine

(S,S)-1,4-bis(benzyloxy)-2,3-epoxybutane

(2R,3R)-2-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-4-penten-2-ol

(2S,3S)-2,3-bis(benzyloxymethyl)azetidine

Downstream raw materials:

(2'S,3'S)-1-<2',3'-bis(benzyloxymethyl)azetidinyl>uracil

(2'S,3'S)-1-<2',3'-bis(benzyloxymethyl)azetidinyl>thymine