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

Base Information

Chemical Name:(S)-4-<(SR)-3-benzyloxy-2-(hydroxymethyl)propyl>-1-tert-butyldimethylsilyl-2-azetidinone
CAS No.:139748-08-6
Molecular Formula:C₂₀H₃₃NO₃Si
Molecular Weight:363.572
Hs Code.:

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

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

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

There total 10 articles about (S)-4-<(SR)-3-benzyloxy-2-(hydroxymethyl)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:

: 113964-32-2
1-{[2-((chloromethyl)allyl)oxy]methyl}-4-methoxybenzene

: 139748-08-6
(S)-4-<(SR)-3-benzyloxy-2-(hydroxymethyl)propyl>-1-tert-butyldimethylsilyl-2-azetidinone

Guidance literature:: Multi-step reaction with 8 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

With sodium hydroxide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; dihydrogen peroxide; tri-n-butyl-tin hydride; magnesium; triethylamine; methylhydrazine; trichloromethyl chloroformate; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; benzene;
DOI:10.1248/cpb.39.2813

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 139748-08-6
(S)-4-<(SR)-3-benzyloxy-2-(hydroxymethyl)propyl>-1-tert-butyldimethylsilyl-2-azetidinone

Guidance literature:: Multi-step reaction with 6 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

With sodium hydroxide; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; dihydrogen peroxide; tri-n-butyl-tin hydride; triethylamine; methylhydrazine; trichloromethyl chloroformate; In dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1248/cpb.39.2813

Reference yield:

: 139747-92-5
(2-benzyloxymethyl-2-propenyl)trimethylsilane

: 139748-08-6
(S)-4-<(SR)-3-benzyloxy-2-(hydroxymethyl)propyl>-1-tert-butyldimethylsilyl-2-azetidinone

Guidance literature:: Multi-step reaction with 7 steps

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

2: 94 percent / NEt₃ / dimethylformamide / 10 h / Ambient temperature

3: methylhydrazine / CH₂Cl₂ / 0 deg C to RT

4: CH₂Cl₂ / 0 °C

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

6: Bu₃SnH, AIBN / benzene / Heating

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

With sodium hydroxide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; dihydrogen peroxide; tri-n-butyl-tin hydride; triethylamine; methylhydrazine; trichloromethyl chloroformate; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; benzene;
DOI:10.1248/cpb.39.2813