(3S,4R,3a'R,5'R,6'S,6a'R)-4-(6'-allyloxy-2',2'-dimethyl-tetrahydrofuro[2',3'-d][1',3']dioxol-5'-yl)-3-phenoxy-azetidin-2-one

Base Information

Chemical Name:(3S,4R,3a'R,5'R,6'S,6a'R)-4-(6'-allyloxy-2',2'-dimethyl-tetrahydrofuro[2',3'-d][1',3']dioxol-5'-yl)-3-phenoxy-azetidin-2-one
CAS No.:547769-48-2
Molecular Formula:C₁₉H₂₃NO₆
Molecular Weight:361.395
Hs Code.:

Synonyms:(3S,4R,3a'R,5'R,6'S,6a'R)-4-(6'-allyloxy-2',2'-dimethyl-tetrahydrofuro[2',3'-d][1',3']dioxol-5'-yl)-3-phenoxy-azetidin-2-one

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Chemical Property of (3S,4R,3a'R,5'R,6'S,6a'R)-4-(6'-allyloxy-2',2'-dimethyl-tetrahydrofuro[2',3'-d][1',3']dioxol-5'-yl)-3-phenoxy-azetidin-2-one

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Technology Process of (3S,4R,3a'R,5'R,6'S,6a'R)-4-(6'-allyloxy-2',2'-dimethyl-tetrahydrofuro[2',3'-d][1',3']dioxol-5'-yl)-3-phenoxy-azetidin-2-one

There total 7 articles about (3S,4R,3a'R,5'R,6'S,6a'R)-4-(6'-allyloxy-2',2'-dimethyl-tetrahydrofuro[2',3'-d][1',3']dioxol-5'-yl)-3-phenoxy-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: 98.0%

: 547769-42-6
(3S,4R,3a'R,5'R,6'S,6a'R)-4-(6'-allyloxy-2',2'-dimethyl-tetrahydrofuro[2',3'-d][1',3']dioxol-5'-yl)-1-(4-methoxyphenyl)-3-phenoxy-azetidin-2-one

: 547769-48-2
(3S,4R,3a'R,5'R,6'S,6a'R)-4-(6'-allyloxy-2',2'-dimethyl-tetrahydrofuro[2',3'-d][1',3']dioxol-5'-yl)-3-phenoxy-azetidin-2-one

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 ℃; for 1h;
DOI:10.1016/S0040-4020(03)00239-4

Reference yield:

: 50-99-7
D-glucose

: 547769-48-2
(3S,4R,3a'R,5'R,6'S,6a'R)-4-(6'-allyloxy-2',2'-dimethyl-tetrahydrofuro[2',3'-d][1',3']dioxol-5'-yl)-3-phenoxy-azetidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: ZnCl₂; H₃PO₄ / 30 h / 20 °C

2: 95 percent / aq. NaOH; TBAB / CH₂Cl₂ / 24 h / 20 °C

3: 100 percent / 70 percent aq. AcOH / 3 h / 70 °C

4: 95 percent / SiO₂-supported NaIO₄

5: MgSO₄ / CH₂Cl₂

6: 79 percent / Et₃N / CH₂Cl₂ / 15 h / 20 °C

7: 98 percent / CAN / acetonitrile; H₂O / 1 h / 0 °C

With sodium hydroxide; sodium periodate; ammonium cerium(IV) nitrate; phosphoric acid; tetrabutylammomium bromide; magnesium sulfate; acetic acid; triethylamine; zinc(II) chloride; In dichloromethane; water; acetonitrile; 6: Staudinger reaction;
DOI:10.1016/S0040-4020(03)00239-4

Reference yield:

: 20316-77-2
(3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

: 547769-48-2
(3S,4R,3a'R,5'R,6'S,6a'R)-4-(6'-allyloxy-2',2'-dimethyl-tetrahydrofuro[2',3'-d][1',3']dioxol-5'-yl)-3-phenoxy-azetidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / 70 percent aq. AcOH / 3 h / 70 °C

2: 95 percent / SiO₂-supported NaIO₄

3: MgSO₄ / CH₂Cl₂

4: 79 percent / Et₃N / CH₂Cl₂ / 15 h / 20 °C

5: 98 percent / CAN / acetonitrile; H₂O / 1 h / 0 °C

With sodium periodate; ammonium cerium(IV) nitrate; magnesium sulfate; acetic acid; triethylamine; In dichloromethane; water; acetonitrile; 4: Staudinger reaction;
DOI:10.1016/S0040-4020(03)00239-4