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

Base Information

• Chemical Name: (2'S,3'S)-1-<2',3'-bis(benzyloxymethyl)azetidinyl>thymine
• CAS No.: 159721-93-4
• Molecular Formula: C₂₄H₂₇N₃O₄
• Molecular Weight: 421.496
• Mol file: 159721-93-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (2'S,3'S)-1-<2',3'-bis(benzyloxymethyl)azetidinyl>thymine 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: 41.0%

(2S,3S)-N1-(methoxy-2-methylacryloyl)ureido-2,3-bis(benzyloxymethyl)azetidine → (2'S,3'S)-1-<2',3'-bis(benzyloxymethyl)azetidinyl>thymine (159721-93-4)

Guidance literature:

With ammonium hydroxide; In ethanol; at 80 ℃; for 8h; sealed tube;

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

Reference yield:

(S,S)-1,4-bis(benzyloxy)-2,3-epoxybutane (81177-24-4) → (2'S,3'S)-1-<2',3'-bis(benzyloxymethyl)azetidinyl>thymine (159721-93-4)

Guidance literature:

Multi-step reaction with 10 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

9: dimethylformamide; benzene / 12 h / Ambient temperature

10: 41 percent / 7percent NH₄OH / ethanol / 8 h / 80 °C / sealed tube

With ammonium hydroxide; 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; benzene;

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

Reference yield:

(2R,3R)-2-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-4-penten-2-ol (113368-83-5) → (2'S,3'S)-1-<2',3'-bis(benzyloxymethyl)azetidinyl>thymine (159721-93-4)

Guidance literature:

Multi-step reaction with 9 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

8: dimethylformamide; benzene / 12 h / Ambient temperature

9: 41 percent / 7percent NH₄OH / ethanol / 8 h / 80 °C / sealed tube

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

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

upstream raw materials:

(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

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