(3S,4R)-1-<<(allyloxy)carbonyl>methyl>-3-<(R)-1-hydroxyethyl>-4-<(triphenylmethyl)thio>-2-azetidinone

Base Information

• Chemical Name: (3S,4R)-1-<<(allyloxy)carbonyl>methyl>-3-<(R)-1-hydroxyethyl>-4-<(triphenylmethyl)thio>-2-azetidinone
• CAS No.: 90762-39-3
• Molecular Formula: C₂₉H₂₉NO₄S
• Molecular Weight: 487.62
• Mol file: 90762-39-3.mol

Synonyms:(3S,4R)-1-<<(allyloxy)carbonyl>methyl>-3-<(R)-1-hydroxyethyl>-4-<(triphenylmethyl)thio>-2-azetidinone

Chemical Property of (3S,4R)-1-<<(allyloxy)carbonyl>methyl>-3-<(R)-1-hydroxyethyl>-4-<(triphenylmethyl)thio>-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-1-<<(allyloxy)carbonyl>methyl>-3-<(R)-1-hydroxyethyl>-4-<(triphenylmethyl)thio>-2-azetidinone

There total 1 articles about (3S,4R)-1-<<(allyloxy)carbonyl>methyl>-3-<(R)-1-hydroxyethyl>-4-<(triphenylmethyl)thio>-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: 95.6%

prop-2-en-1-yl 2-iodoacetate (90711-60-7) + (3S,4R)-3-<(R)-hydroxyethyl>-4-<(triphenylmethyl)thio>-2-azetidinone (87037-99-8) → (3S,4R)-1-<<(allyloxy)carbonyl>methyl>-3-<(R)-1-hydroxyethyl>-4-<(triphenylmethyl)thio>-2-azetidinone (90762-39-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 50 - 55 ℃; for 2.5h;

DOI:10.1016/S0040-4020(01)90781-1

Reference yield: 100.0%

3,4-dihydro-2H-pyran (110-87-2) + (3S,4R)-1-<<(allyloxy)carbonyl>methyl>-3-<(R)-1-hydroxyethyl>-4-<(triphenylmethyl)thio>-2-azetidinone (90762-39-3) → (3S,4R)-1-<<(allyloxy)carbonyl>methyl>-3-<(R)-1-(tetrahydropyranyloxy)ethyl>-4-<(triphenylmethyl)thio>-2-azetidinone (104715-49-3)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 30 ℃; for 5h;

DOI:10.1021/jo00373a033

Reference yield:

(3S,4R)-1-<<(allyloxy)carbonyl>methyl>-3-<(R)-1-hydroxyethyl>-4-<(triphenylmethyl)thio>-2-azetidinone (90762-39-3) → (5R,6S)-2-<<2-(carbamoyloxy)ethyl>thio>-6-<(R)-1-hydroxyethyl>penem-3-carboxylic acid (95415-91-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) AgNO₃, pyridine, 2) pyridine / 1) MeOH, RT, 2h, 2a) THF, 40 deg C, 0.5h, 2b) 0.75 h, reflux

2: imidazole / tetrahydrofuran / 0.25 h / Ambient temperature

3: 1) lithium hexamethyldisilazide (LiHMDS), 2) glacial HOAc / 1) THF, -40 deg C, 15 min

4: Na₂CO₃ / H₂O / 20 h / Ambient temperature

5: H₃PO₄ / tetrahydrofuran; H₂O / 2.5 h / Ambient temperature

6: 1) PPh₃, 2) sodium 2-ethylhexanoate, (BuO)3P / 1) bis(triisopropylphosphite) palladium dichloride / 1) THF, RT, 15 min, 2) 10 min

With pyridine; 1H-imidazole; tri-n-butyl phosphite; phosphoric acid; sodium carbonate; silver nitrate; acetic acid; triphenylphosphine; lithium hexamethyldisilazane; sodium 2-ethylhexanoic acid; {[(OⁱPr)₃P]₂PdCl₂}; In tetrahydrofuran; water;

DOI:10.1016/S0040-4020(01)90781-1

upstream raw materials:

prop-2-en-1-yl 2-iodoacetate

(3S,4R)-3-<(R)-hydroxyethyl>-4-<(triphenylmethyl)thio>-2-azetidinone

Downstream raw materials:

(3S,4R)-1-<<(allyloxy)carbonyl>methyl>-3-<(R)-1-(tetrahydropyranyloxy)ethyl>-4-<(triphenylmethyl)thio>-2-azetidinone

(5R,6S)-2-<<2-(carbamoyloxy)ethyl>thio>-6-<(R)-1-hydroxyethyl>penem-3-carboxylic acid