cis-1-benzyl-3S-benzyloxy-4R-[1'R,2'S,3'R,4'-di-O-isopropylidene]butyl-azetidin-2-one

Base Information

• Chemical Name: cis-1-benzyl-3S-benzyloxy-4R-[1'R,2'S,3'R,4'-di-O-isopropylidene]butyl-azetidin-2-one
• CAS No.: 146467-03-0
• Molecular Formula: C₂₇H₃₃NO₆
• Molecular Weight: 467.562

Synonyms:cis-1-benzyl-3S-benzyloxy-4R-[1'R,2'S,3'R,4'-di-O-isopropylidene]butyl-azetidin-2-one

Chemical Property of cis-1-benzyl-3S-benzyloxy-4R-[1'R,2'S,3'R,4'-di-O-isopropylidene]butyl-azetidin-2-one

Chemical Property:

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Technology Process of cis-1-benzyl-3S-benzyloxy-4R-[1'R,2'S,3'R,4'-di-O-isopropylidene]butyl-azetidin-2-one

There total 3 articles about cis-1-benzyl-3S-benzyloxy-4R-[1'R,2'S,3'R,4'-di-O-isopropylidene]butyl-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: 72.0%

Benzyl-[1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-meth-(Z)-ylidene]-amine (142913-83-5) + Benzyloxyacetyl chloride (19810-31-2) → cis-1-benzyl-3S-benzyloxy-4R-[1'R,2'S,3'R,4'-di-O-isopropylidene]butyl-azetidin-2-one (146467-03-0)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1021/jo00054a007

Reference yield: 65.0%

Benzyloxyacetyl chloride (19810-31-2) + 2,3;4,5-di-O-isopropylidene-D-arabinose N-benzylimine (142913-83-5) → cis-1-benzyl-3S-benzyloxy-4R-[1'R,2'S,3'R,4'-di-O-isopropylidene]butyl-azetidin-2-one (146467-03-0)

Guidance literature:

With triethylamine; In dichloromethane; at -20 - 25 ℃; Inert atmosphere;

DOI:10.1039/c4ob00948g

Reference yield:

Benzyl-[1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-meth-(E)-ylidene]-amine + potassium; benzyloxy-acetate → cis-1-benzyl-3S-benzyloxy-4R-[1'R,2'S,3'R,4'-di-O-isopropylidene]butyl-azetidin-2-one (146467-03-0)

Guidance literature:

With 1,3,5-trichloro-2,4,6-triazine; triethylamine; In dichloromethane; at -20 ℃;

DOI:10.1016/S0040-4020(00)00410-5

upstream raw materials:

Benzyl-[1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-meth-(Z)-ylidene]-amine

Benzyloxyacetyl chloride

2,3;4,5-di-O-isopropylidene-D-arabinose N-benzylimine

Downstream raw materials:

1-benzyl-3S-benzyloxy-4R-[1'R,2'S-O-isopropylidene-3'R,4'-dihydroxy]butyl azetidin-2-one

1-benzyl-3S-hydroxy-4R-[1'R,2'R-O-isopropylidene-3'-hydroxy]propyl-azetidin-2-one

1-benzyl-3S-benzyloxy-4R-[1'R,2'R-O-isopropylidene-3'-hydroxy]propyl-azetidin-2-one

1-benzyl-3S-benzyloxy-4R-[1'R,2'S-O-isopropylidene-3-oxo]propyl-azetidin-2-one

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