(+)-(3R,4S)-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propenyl)-2-azetidinone

Base Information

• Chemical Name: (+)-(3R,4S)-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propenyl)-2-azetidinone
• CAS No.: 253599-39-2
• Molecular Formula: C₁₈H₂₃NO₄
• Molecular Weight: 317.385

Synonyms:(+)-(3R,4S)-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propenyl)-2-azetidinone

Chemical Property of (+)-(3R,4S)-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propenyl)-2-azetidinone

Chemical Property:

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Technology Process of (+)-(3R,4S)-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propenyl)-2-azetidinone

There total 4 articles about (+)-(3R,4S)-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propenyl)-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: 82.0%

Benzyloxyacetyl chloride (19810-31-2) + Allyl-[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(Z)-ylidene]-amine → (+)-(3R,4S)-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propenyl)-2-azetidinone (253599-39-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 16h;

DOI:10.1002/ejoc.200400792

Reference yield: 65.0%

Benzyloxyacetyl chloride (19810-31-2) + Allyl-[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-amine (358973-81-6) → (+)-(3R,4S)-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propenyl)-2-azetidinone (253599-39-2)

Guidance literature:

With triethylamine; In dichloromethane; at -20 - 20 ℃; for 18h;

DOI:10.1016/S0040-4020(99)00867-4

Reference yield:

2,3-isopropylidene-glyceraldehyde (15186-48-8) → (+)-(3R,4S)-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propenyl)-2-azetidinone (253599-39-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.16 g / MgSO₄ / CH₂Cl₂ / 2.5 h / 0 °C

2: 65 percent / Et₃N / CH₂Cl₂ / 18 h / -20 - 20 °C

With magnesium sulfate; triethylamine; In dichloromethane; 1: Condensation / 2: Cycloaddition;

DOI:10.1016/S0040-4020(99)00867-4

upstream raw materials:

Benzyloxyacetyl chloride

Allyl-[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-amine

2,3-isopropylidene-glyceraldehyde

Downstream raw materials:

(+)-cis-1-allyl-3-(R)-benzyloxy-4-(S)-[1-(S),2-dihydroxyethyl]-azetidin-2-one

(+)-(3R,4R)-3-benzyloxy-1-(2-propenyl)-4-oxoazetidine-2-carbaldehyde

(1S,2S,3R,7R)-3-Benzyloxy-9-methyl-8-oxa-5,9-diaza-tricyclo[5.2.1.0^2,5]decan-4-one

(R)-2-Benzyloxy-2-((1S,2S,5R)-7-methyl-6-oxa-3,7-diaza-bicyclo[3.2.1]oct-2-yl)-ethanol

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