(4S,5S,3'R,4'S,3''S,4''R)-2,2-Dimethyl-4,5-bis<1'-(p-methoxyphenyl)-3'-(benzyloxy)-2'-oxo-azetidin-4'-yl>-1,3-dioxolane

Base Information

• Chemical Name: (4S,5S,3'R,4'S,3''S,4''R)-2,2-Dimethyl-4,5-bis<1'-(p-methoxyphenyl)-3'-(benzyloxy)-2'-oxo-azetidin-4'-yl>-1,3-dioxolane
• CAS No.: 153545-43-8
• Molecular Formula: C₃₉H₄₀N₂O₈
• Molecular Weight: 664.755
• Mol file: 153545-43-8.mol

Synonyms:(4S,5S,3'R,4'S,3''S,4''R)-2,2-Dimethyl-4,5-bis<1'-(p-methoxyphenyl)-3'-(benzyloxy)-2'-oxo-azetidin-4'-yl>-1,3-dioxolane

Chemical Property of (4S,5S,3'R,4'S,3''S,4''R)-2,2-Dimethyl-4,5-bis<1'-(p-methoxyphenyl)-3'-(benzyloxy)-2'-oxo-azetidin-4'-yl>-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S,3'R,4'S,3''S,4''R)-2,2-Dimethyl-4,5-bis<1'-(p-methoxyphenyl)-3'-(benzyloxy)-2'-oxo-azetidin-4'-yl>-1,3-dioxolane

There total 3 articles about (4S,5S,3'R,4'S,3''S,4''R)-2,2-Dimethyl-4,5-bis<1'-(p-methoxyphenyl)-3'-(benzyloxy)-2'-oxo-azetidin-4'-yl>-1,3-dioxolane 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: 56.0%

Benzyloxyacetyl chloride (19810-31-2) + C21H24N2O4 (153472-20-9) → (4S,5S,3'R,4'S,3''S,4''R)-2,2-Dimethyl-4,5-bis<1'-(p-methoxyphenyl)-3'-(benzyloxy)-2'-oxo-azetidin-4'-yl>-1,3-dioxolane (153545-43-8) + C39H40N2O8 (153472-25-4)

Guidance literature:

With triethylamine; In dichloromethane; for 14h; Ambient temperature;

DOI:10.1021/jo00083a042

Reference yield:

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (59779-75-8) → (4S,5S,3'R,4'S,3''S,4''R)-2,2-Dimethyl-4,5-bis<1'-(p-methoxyphenyl)-3'-(benzyloxy)-2'-oxo-azetidin-4'-yl>-1,3-dioxolane (153545-43-8)

Guidance literature:

Multi-step reaction with 3 steps

1: DIBALH / toluene / 3 h / -78 °C

2: toluene / 20 h / Ambient temperature

3: 25 percent / Et₃N / CH₂Cl₂ / 14 h / Ambient temperature

With diisobutylaluminium hydride; triethylamine; In dichloromethane; toluene;

DOI:10.1021/jo00083a042

Reference yield:

(4R,5R)-2,2-Dimethyl-[1,3]dioxolane-4,5-dicarbaldehyde (122137-20-6) → (4S,5S,3'R,4'S,3''S,4''R)-2,2-Dimethyl-4,5-bis<1'-(p-methoxyphenyl)-3'-(benzyloxy)-2'-oxo-azetidin-4'-yl>-1,3-dioxolane (153545-43-8)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 20 h / Ambient temperature

2: 25 percent / Et₃N / CH₂Cl₂ / 14 h / Ambient temperature

With triethylamine; In dichloromethane; toluene;

DOI:10.1021/jo00083a042

upstream raw materials:

Benzyloxyacetyl chloride

C₂₁H₂₄N₂O₄

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

(4R,5R)-2,2-Dimethyl-[1,3]dioxolane-4,5-dicarbaldehyde

Downstream raw materials:

cis-1-(p-methoxyphenyl)-3-benzyloxy-4-formyl-2-azetidinone

(1S,2S,3'R,4'S,3''S,4''R)-1,2-Bis<1'-(p-methoxyphenyl)-3'-(benzyloxy)-2'-oxo-azetidin-4'-yl>ethane-1,2-diol