(3R,4S)-3-benzyloxy-1-(3-butenyl)-4-[(R)-1-hydroxy-3-butenyl]-2-azetidinone

Base Information

• Chemical Name: (3R,4S)-3-benzyloxy-1-(3-butenyl)-4-[(R)-1-hydroxy-3-butenyl]-2-azetidinone
• CAS No.: 277757-91-2
• Molecular Formula: C₁₈H₂₃NO₃
• Molecular Weight: 301.386
• Mol file: 277757-91-2.mol

Synonyms:(3R,4S)-3-benzyloxy-1-(3-butenyl)-4-[(R)-1-hydroxy-3-butenyl]-2-azetidinone

Chemical Property of (3R,4S)-3-benzyloxy-1-(3-butenyl)-4-[(R)-1-hydroxy-3-butenyl]-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-3-benzyloxy-1-(3-butenyl)-4-[(R)-1-hydroxy-3-butenyl]-2-azetidinone

There total 5 articles about (3R,4S)-3-benzyloxy-1-(3-butenyl)-4-[(R)-1-hydroxy-3-butenyl]-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: 54.0%

(+)-(3R,4R)-2-benzyloxy-1-(3-butenyl)-4-formyl-2-azetidinone (277757-70-7) + allyl-trimethyl-silane (762-72-1) → (3R,4S)-3-benzyloxy-1-(3-butenyl)-4-[(R)-1-hydroxy-3-butenyl]-2-azetidinone (277757-91-2)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at -78 ℃; for 0.75h;

DOI:10.1021/jo991641j

Reference yield:

Benzyloxyacetyl chloride (19810-31-2) → (3R,4S)-3-benzyloxy-1-(3-butenyl)-4-[(R)-1-hydroxy-3-butenyl]-2-azetidinone (277757-91-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 58 percent / Et₃N / CH₂Cl₂ / 16 h / 20 °C

2: 100 percent / p-TsOH*H₂O / tetrahydrofuran; H₂O / 2 h / Heating

3: sodium hydrogen carbonate; sodium periodate / CH₂Cl₂; H₂O / 2 h

4: 54 percent / SnCl₄ / CH₂Cl₂ / 0.75 h / -78 °C

With sodium periodate; tin(IV) chloride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; 1: Staudinger reaction / 2: Hydrolysis / 3: oxidative cleavage / 4: Addition;

DOI:10.1021/jo991641j

Reference yield:

(+)-(3R,4S)-3-benzyloxy-1-(3-butenyl)-4-[(S)-1,2-dihydroxyethylen]-2-azetidinone (277757-81-0) → (3R,4S)-3-benzyloxy-1-(3-butenyl)-4-[(R)-1-hydroxy-3-butenyl]-2-azetidinone (277757-91-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogen carbonate; sodium periodate / CH₂Cl₂; H₂O / 2 h

2: 54 percent / SnCl₄ / CH₂Cl₂ / 0.75 h / -78 °C

With sodium periodate; tin(IV) chloride; sodium hydrogencarbonate; In dichloromethane; water; 1: oxidative cleavage / 2: Addition;

DOI:10.1021/jo991641j

upstream raw materials:

(+)-(3R,4R)-2-benzyloxy-1-(3-butenyl)-4-formyl-2-azetidinone

allyl-trimethyl-silane

Benzyloxyacetyl chloride

(+)-(3R,4S)-3-benzyloxy-1-(3-butenyl)-4-[(S)-1,2-dihydroxyethylen]-2-azetidinone