(3R,4S)-3-Benzyloxy-1-but-3-ynyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-azetidin-2-one

Base Information

• Chemical Name: (3R,4S)-3-Benzyloxy-1-but-3-ynyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-azetidin-2-one
• CAS No.: 182963-07-1
• Molecular Formula: C₁₉H₂₃NO₄
• Molecular Weight: 329.396
• Mol file: 182963-07-1.mol

Synonyms:(3R,4S)-3-Benzyloxy-1-but-3-ynyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-azetidin-2-one

Chemical Property of (3R,4S)-3-Benzyloxy-1-but-3-ynyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-3-Benzyloxy-1-but-3-ynyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-azetidin-2-one

There total 1 articles about (3R,4S)-3-Benzyloxy-1-but-3-ynyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-azetidin-2-one 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%

Benzyloxyacetyl chloride (19810-31-2) + But-3-ynyl-[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-amine → (3R,4S)-3-Benzyloxy-1-but-3-ynyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-azetidin-2-one (182963-07-1)

Guidance literature:

With triethylamine; In benzene; Ambient temperature;

DOI:10.1021/jo980114h

Reference yield:

(3R,4S)-3-Benzyloxy-1-but-3-ynyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-azetidin-2-one (182963-07-1) → (1R,8aS,8bS)-1-Benzyloxy-1,4,5,8,8a,8b-hexahydro-azeto[1,2-a]cyclopenta[c]pyridine-2,7-dione

Guidance literature:

Multi-step reaction with 3 steps

1: p-TsOH*H₂O / tetrahydrofuran; H₂O / Heating

2: 1.) 1,1-thiocarbonyldiimidazole, 2.) P(OEt)3 / 1.) THF, reflux, 2.) reflux.

3: 95 percent / toluene / 1.) room temperature, 1 h, 2.) reflux, 2 h.

With toluene-4-sulfonic acid; 1,1'-Thiocarbonyldiimidazole; triethyl phosphite; In tetrahydrofuran; water; toluene;

DOI:10.1021/jo980114h

Reference yield:

(3R,4S)-3-Benzyloxy-1-but-3-ynyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-azetidin-2-one (182963-07-1) → (3R,4S)-3-Benzyloxy-1-but-3-ynyl-4-((S)-1,2-dihydroxy-ethyl)-azetidin-2-one (214477-52-8)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; water; Yield given; Heating;

DOI:10.1021/jo980114h

upstream raw materials:

Benzyloxyacetyl chloride

Downstream raw materials:

(+)-(3R,4S)-3-(benzyloxy)-1-(3-butynyl)-4-vinyl-2-azetidinone

(3R,4S)-3-Benzyloxy-1-but-3-ynyl-4-((S)-1,2-dihydroxy-ethyl)-azetidin-2-one