cis-1-(p-anisyl)-3'R-(4-acetoxy-5-hydro-2,3-dienyl-α-O-glycoside)-4S-(2,2'-dimethyl-1',3'-dioxalanyl)azetidin-2-one

Base Information

Chemical Name:cis-1-(p-anisyl)-3'R-(4-acetoxy-5-hydro-2,3-dienyl-α-O-glycoside)-4S-(2,2'-dimethyl-1',3'-dioxalanyl)azetidin-2-one
CAS No.:1415716-24-3
Molecular Formula:C₂₂H₂₇NO₈
Molecular Weight:433.458
Hs Code.:

Synonyms:cis-1-(p-anisyl)-3'R-(4-acetoxy-5-hydro-2,3-dienyl-α-O-glycoside)-4S-(2,2'-dimethyl-1',3'-dioxalanyl)azetidin-2-one

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Chemical Property of cis-1-(p-anisyl)-3'R-(4-acetoxy-5-hydro-2,3-dienyl-α-O-glycoside)-4S-(2,2'-dimethyl-1',3'-dioxalanyl)azetidin-2-one

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Technology Process of cis-1-(p-anisyl)-3'R-(4-acetoxy-5-hydro-2,3-dienyl-α-O-glycoside)-4S-(2,2'-dimethyl-1',3'-dioxalanyl)azetidin-2-one

There total 3 articles about cis-1-(p-anisyl)-3'R-(4-acetoxy-5-hydro-2,3-dienyl-α-O-glycoside)-4S-(2,2'-dimethyl-1',3'-dioxalanyl)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: 65.0%

: 115828-87-0
(3R,4S)-cis-1-(p-anisyl)-3-hydroxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

: 3152-43-0
3,4-di-O-acetyl-D-xylal

: 1415716-24-3
cis-1-(p-anisyl)-3'R-(4-acetoxy-5-hydro-2,3-dienyl-α-O-glycoside)-4S-(2,2'-dimethyl-1',3'-dioxalanyl)azetidin-2-one

Guidance literature:: With iodine; In tetrahydrofuran; at 20 ℃; for 30h; stereospecific reaction;
DOI:10.1016/j.tet.2012.01.078

Reference yield:

: 103239-04-9
N-(p-anisyl)-4-<(S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>-methylene-imine

: 1415716-24-3
cis-1-(p-anisyl)-3'R-(4-acetoxy-5-hydro-2,3-dienyl-α-O-glycoside)-4S-(2,2'-dimethyl-1',3'-dioxalanyl)azetidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 4-methyl-morpholine / dichloromethane / Microwave irradiation

2: ammonium formate; hydrogen; palladium on activated charcoal / Microwave irradiation

3: iodine / tetrahydrofuran / 30 h / 20 °C

With 4-methyl-morpholine; palladium on activated charcoal; hydrogen; iodine; ammonium formate; In tetrahydrofuran; dichloromethane; 3: |Ferrier Carbohydrate Rearrangement;
DOI:10.1016/j.tet.2012.01.078

Reference yield:

: 115857-84-6
(3R,4S)-3-(Benzyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-1-(4-methoxyphenyl)azetidin-2-one

: 1415716-24-3
cis-1-(p-anisyl)-3'R-(4-acetoxy-5-hydro-2,3-dienyl-α-O-glycoside)-4S-(2,2'-dimethyl-1',3'-dioxalanyl)azetidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: ammonium formate; hydrogen; palladium on activated charcoal / Microwave irradiation

2: iodine / tetrahydrofuran / 30 h / 20 °C

With palladium on activated charcoal; hydrogen; iodine; ammonium formate; In tetrahydrofuran; 2: |Ferrier Carbohydrate Rearrangement;
DOI:10.1016/j.tet.2012.01.078