(S)-4-<(S)-3-benzyloxy-2-(iodomethyl)propyl>-1-tert-butyldimethylsilyl-2-azetidinone

Base Information

• Chemical Name: (S)-4-<(S)-3-benzyloxy-2-(iodomethyl)propyl>-1-tert-butyldimethylsilyl-2-azetidinone
• CAS No.: 139748-02-0
• Molecular Formula: C₂₀H₃₂INO₂Si
• Molecular Weight: 473.47
• Mol file: 139748-02-0.mol

Synonyms:(S)-4-<(S)-3-benzyloxy-2-(iodomethyl)propyl>-1-tert-butyldimethylsilyl-2-azetidinone

Chemical Property of (S)-4-<(S)-3-benzyloxy-2-(iodomethyl)propyl>-1-tert-butyldimethylsilyl-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-<(S)-3-benzyloxy-2-(iodomethyl)propyl>-1-tert-butyldimethylsilyl-2-azetidinone

There total 17 articles about (S)-4-<(S)-3-benzyloxy-2-(iodomethyl)propyl>-1-tert-butyldimethylsilyl-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: 100.0%

(S)-4-<(S)-2-benzyloxymethyl-3-(p-toluenesulfonyloxy)propyl>-1-tert-butyldimethylsilyl-2-azetidinone (139748-00-8) → (S)-4-<(S)-3-benzyloxy-2-(iodomethyl)propyl>-1-tert-butyldimethylsilyl-2-azetidinone (139748-02-0)

Guidance literature:

With sodium iodide; In acetone; for 2h; Heating;

DOI:10.1248/cpb.39.2813

Reference yield:

1-{[2-((chloromethyl)allyl)oxy]methyl}-4-methoxybenzene (113964-32-2) → (S)-4-<(S)-3-benzyloxy-2-(iodomethyl)propyl>-1-tert-butyldimethylsilyl-2-azetidinone (139748-02-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 77 percent / Mg / tetrahydrofuran / 1 h / Heating

2: 79 percent / TMSOTf / 1,2-dichloro-ethane / 5 h / 45 - 50 °C

3: 94 percent / NEt₃ / dimethylformamide / 10 h / Ambient temperature

4: methylhydrazine / CH₂Cl₂ / 0 deg C to RT

5: CH₂Cl₂ / 0 °C

6: Cl₃COC(O)Cl, NEt₃ / CH₂Cl₂ / -50 °C

7: Bu₃SnH, AIBN / benzene / Heating

8: 1) BH₃*Me₂S, 2) H₂O₂, NaOH / 1) THF, 0 deg C, 2) H₂O, 0 deg C

9: 85 percent / pyridine / Ambient temperature

10: 100 percent / NaI / acetone / 2 h / Heating

With pyridine; sodium hydroxide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; dihydrogen peroxide; tri-n-butyl-tin hydride; magnesium; triethylamine; methylhydrazine; sodium iodide; trichloromethyl chloroformate; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1248/cpb.39.2813

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (S)-4-<(S)-3-benzyloxy-2-(iodomethyl)propyl>-1-tert-butyldimethylsilyl-2-azetidinone (139748-02-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 94 percent / NEt₃ / dimethylformamide / 10 h / Ambient temperature

2: methylhydrazine / CH₂Cl₂ / 0 deg C to RT

3: CH₂Cl₂ / 0 °C

4: Cl₃COC(O)Cl, NEt₃ / CH₂Cl₂ / -50 °C

5: Bu₃SnH, AIBN / benzene / Heating

6: 1) BH₃*Me₂S, 2) H₂O₂, NaOH / 1) THF, 0 deg C, 2) H₂O, 0 deg C

7: 85 percent / pyridine / Ambient temperature

8: 100 percent / NaI / acetone / 2 h / Heating

With pyridine; sodium hydroxide; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; dihydrogen peroxide; tri-n-butyl-tin hydride; triethylamine; methylhydrazine; sodium iodide; trichloromethyl chloroformate; In dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1248/cpb.39.2813

upstream raw materials:

(S)-4-<(S)-2-benzyloxymethyl-3-(p-toluenesulfonyloxy)propyl>-1-tert-butyldimethylsilyl-2-azetidinone

1-{[2-((chloromethyl)allyl)oxy]methyl}-4-methoxybenzene

tert-butyldimethylsilyl chloride

(2-benzyloxymethyl-2-propenyl)trimethylsilane

Downstream raw materials:

(S)-4-<(S)-3-benzyloxy-2-(iodomethyl)propyl>-2-azetidinone

(3R,5S)-3-benzyloxymethyl-1-azabicyclo<3.2.0>heptan-7-one