(3S,1'R)-1-benzyloxy-3-<<2-(tert-butyldimethylsilyl)oxy>ethyl>-2-azetidinone

Base Information

• Chemical Name: (3S,1'R)-1-benzyloxy-3-<<2-(tert-butyldimethylsilyl)oxy>ethyl>-2-azetidinone
• CAS No.: 152996-74-2
• Molecular Formula: C₁₈H₂₉NO₃Si
• Molecular Weight: 335.519
• Mol file: 152996-74-2.mol

Synonyms:(3S,1'R)-1-benzyloxy-3-<<2-(tert-butyldimethylsilyl)oxy>ethyl>-2-azetidinone

Chemical Property of (3S,1'R)-1-benzyloxy-3-<<2-(tert-butyldimethylsilyl)oxy>ethyl>-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,1'R)-1-benzyloxy-3-<<2-(tert-butyldimethylsilyl)oxy>ethyl>-2-azetidinone

There total 7 articles about (3S,1'R)-1-benzyloxy-3-<<2-(tert-butyldimethylsilyl)oxy>ethyl>-2-azetidinone 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: 92.5%

t-butyldimethylsiyl triflate (69739-34-0) + (S)-1-Benzyloxy-3-((R)-1-hydroxy-ethyl)-azetidin-2-one (152996-73-1) → (3S,1'R)-1-benzyloxy-3-<<2-(tert-butyldimethylsilyl)oxy>ethyl>-2-azetidinone (152996-74-2)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; for 3h;

DOI:10.1016/S0040-4020(01)87214-8

Reference yield:

(2R,3R)-4-<<(t-butyldimethyl)silyl>oxy>-3-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-2-butanol (152996-67-3) → (3S,1'R)-1-benzyloxy-3-<<2-(tert-butyldimethylsilyl)oxy>ethyl>-2-azetidinone (152996-74-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

2: 69.8 percent / 4 Angstroem molecular sieves, 1 M p-toluenesulfonic acid monohydrate / propan-2-ol

3: Jones reagent / acetone / 0.33 h

4: 1.) N-hydroxybenzotriazole hydrate, DCC; 2.) triethylamine / 1.) CH₃CN, 1 h, r.t; 2.) overnight, r.t.

5: DDQ / CH₂Cl₂; 2-methyl-propan-2-ol / 2 h / Ambient temperature; pH = 7

6: 91 percent / Ph₃P, DEAD / tetrahydrofuran / Ambient temperature

7: 80 percent / 0.5 M n-Bu₄NF*3H₂O / tetrahydrofuran / 1 h / Ambient temperature

8: 92.5 percent / 2,6-lutidine / CH₂Cl₂ / 3 h

With 2,6-dimethylpyridine; jones reagent; 4 A molecular sieve; tetrabutyl ammonium fluoride; benzotriazol-1-ol; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; isopropyl alcohol; acetone; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)87214-8

Reference yield:

(3S,1'R)-1-benzyloxy-3-<<2-(tri-iso-propylsilyl)oxy>ethyl>-2-azetidinone (152996-72-0) → (3S,1'R)-1-benzyloxy-3-<<2-(tert-butyldimethylsilyl)oxy>ethyl>-2-azetidinone (152996-74-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / 0.5 M n-Bu₄NF*3H₂O / tetrahydrofuran / 1 h / Ambient temperature

2: 92.5 percent / 2,6-lutidine / CH₂Cl₂ / 3 h

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(01)87214-8

upstream raw materials:

t-butyldimethylsiyl triflate

(S)-1-Benzyloxy-3-((R)-1-hydroxy-ethyl)-azetidin-2-one

(2R,3R)-4-<<(t-butyldimethyl)silyl>oxy>-3-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-2-butanol

(3S,1'R)-1-benzyloxy-3-<<2-(tri-iso-propylsilyl)oxy>ethyl>-2-azetidinone