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

Base Information

Chemical Name:(3S,4R,3a'R,5'R,6'S,6a'R)-4-(6'-benzyloxy-2',2'-dimethyl-tetrahydrofuro[2',3'-d][1',3']dioxol-5'-yl)-1-(4-methoxyphenyl)-3-phenoxy-azetidin-2-one
CAS No.:547769-37-9
Molecular Formula:C₃₀H₃₁NO₇
Molecular Weight:517.579
Hs Code.:

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

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

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

There total 5 articles about (3S,4R,3a'R,5'R,6'S,6a'R)-4-(6'-benzyloxy-2',2'-dimethyl-tetrahydrofuro[2',3'-d][1',3']dioxol-5'-yl)-1-(4-methoxyphenyl)-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:

: 50-99-7
D-glucose

: 547769-37-9
(3S,4R,3a'R,5'R,6'S,6a'R)-4-(6'-benzyloxy-2',2'-dimethyl-tetrahydrofuro[2',3'-d][1',3']dioxol-5'-yl)-1-(4-methoxyphenyl)-3-phenoxy-azetidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: ZnCl₂; H₃PO₄ / 30 h / 20 °C

2: 97 percent / NaH / dimethylformamide / 2.5 h / 20 °C

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

4: 96 percent / SiO₂-supported NaIO₄

5: MgSO₄ / CH₂Cl₂

6: 75 percent / Et₃N / CH₂Cl₂ / 15 h / 20 °C

With sodium periodate; phosphoric acid; sodium hydride; magnesium sulfate; acetic acid; triethylamine; zinc(II) chloride; In dichloromethane; N,N-dimethyl-formamide; 6: Staudinger reaction;
DOI:10.1016/S0040-4020(03)00239-4

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 547769-37-9
(3S,4R,3a'R,5'R,6'S,6a'R)-4-(6'-benzyloxy-2',2'-dimethyl-tetrahydrofuro[2',3'-d][1',3']dioxol-5'-yl)-1-(4-methoxyphenyl)-3-phenoxy-azetidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 96 percent / SiO₂-supported NaIO₄

2: MgSO₄ / CH₂Cl₂

3: 75 percent / Et₃N / CH₂Cl₂ / 15 h / 20 °C

With sodium periodate; magnesium sulfate; triethylamine; In dichloromethane; 3: Staudinger reaction;
DOI:10.1016/S0040-4020(03)00239-4

Reference yield:

: 18685-18-2
3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

: 547769-37-9
(3S,4R,3a'R,5'R,6'S,6a'R)-4-(6'-benzyloxy-2',2'-dimethyl-tetrahydrofuro[2',3'-d][1',3']dioxol-5'-yl)-1-(4-methoxyphenyl)-3-phenoxy-azetidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

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

2: 96 percent / SiO₂-supported NaIO₄

3: MgSO₄ / CH₂Cl₂

4: 75 percent / Et₃N / CH₂Cl₂ / 15 h / 20 °C

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