(3S,4S)-4-(2-benzyloxymethyl-2-propenyl)-1-tert-butyldimethylsilyl-3-phthalimido-2-azetidinone

Base Information

• Chemical Name: (3S,4S)-4-(2-benzyloxymethyl-2-propenyl)-1-tert-butyldimethylsilyl-3-phthalimido-2-azetidinone
• CAS No.: 139747-95-8
• Molecular Formula: C₂₈H₃₄N₂O₄Si
• Molecular Weight: 490.674
• Mol file: 139747-95-8.mol

Synonyms:(3S,4S)-4-(2-benzyloxymethyl-2-propenyl)-1-tert-butyldimethylsilyl-3-phthalimido-2-azetidinone

Chemical Property of (3S,4S)-4-(2-benzyloxymethyl-2-propenyl)-1-tert-butyldimethylsilyl-3-phthalimido-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-4-(2-benzyloxymethyl-2-propenyl)-1-tert-butyldimethylsilyl-3-phthalimido-2-azetidinone

There total 6 articles about (3S,4S)-4-(2-benzyloxymethyl-2-propenyl)-1-tert-butyldimethylsilyl-3-phthalimido-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: 94.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (3S,4S)-4-(2-benzyloxymethyl-2-propenyl)-3-phthalimido-2-azetidinone (139747-94-7) → (3S,4S)-4-(2-benzyloxymethyl-2-propenyl)-1-tert-butyldimethylsilyl-3-phthalimido-2-azetidinone (139747-95-8)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; for 10h; Ambient temperature;

DOI:10.1248/cpb.39.2813

Reference yield:

1-{[2-((chloromethyl)allyl)oxy]methyl}-4-methoxybenzene (113964-32-2) → (3S,4S)-4-(2-benzyloxymethyl-2-propenyl)-1-tert-butyldimethylsilyl-3-phthalimido-2-azetidinone (139747-95-8)

Guidance literature:

Multi-step reaction with 3 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

With trimethylsilyl trifluoromethanesulfonate; magnesium; triethylamine; In tetrahydrofuran; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.39.2813

Reference yield:

(3S,4S)-4-acetoxy-3-phthalimido-2-azetidinone (70267-78-6) → (3S,4S)-4-(2-benzyloxymethyl-2-propenyl)-1-tert-butyldimethylsilyl-3-phthalimido-2-azetidinone (139747-95-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / NEt₃ / CH₂Cl₂ / 0.83 h / 0 °C

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

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

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.39.2813

upstream raw materials:

tert-butyldimethylsilyl chloride

(3S,4S)-4-(2-benzyloxymethyl-2-propenyl)-3-phthalimido-2-azetidinone

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

(3S,4S)-4-acetoxy-3-phthalimido-2-azetidinone

Downstream raw materials:

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

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

(S)-4-<(R)-2-benzyloxymethyl-3-(tert-butyldimethylsilyloxy)propyl>-2-azetidinone

(S)-4-(2-benzyloxymethyl-2-propenyl)-1-tert-butyldimethylsilyl-2-azetidinone