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

Base Information

• Chemical Name: 1-benzyl-3S-benzyloxy-4R-[1'R,2'S-O-isopropylidene-3-oxo]propyl-azetidin-2-one
• CAS No.: 146467-05-2
• Molecular Formula: C₂₃H₂₅NO₅
• Molecular Weight: 395.455

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

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

Chemical Property:

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

There total 2 articles about 1-benzyl-3S-benzyloxy-4R-[1'R,2'S-O-isopropylidene-3-oxo]propyl-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: 90.0%

1-benzyl-3S-benzyloxy-4R-[1'R,2'S-O-isopropylidene-3'R,4'-dihydroxy]butyl azetidin-2-one (146467-04-1) → 1-benzyl-3S-benzyloxy-4R-[1'R,2'S-O-isopropylidene-3-oxo]propyl-azetidin-2-one (146467-05-2)

Guidance literature:

With sodium periodate; In water; acetonitrile;

DOI:10.1021/jo00054a007

Reference yield:

cis-1-benzyl-3S-benzyloxy-4R-[1'R,2'S,3'R,4'-di-O-isopropylidene]butyl-azetidin-2-one (146467-03-0) → 1-benzyl-3S-benzyloxy-4R-[1'R,2'S-O-isopropylidene-3-oxo]propyl-azetidin-2-one (146467-05-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / aq. AcOH / methanol / 60 h / 20 °C

2: 90 percent / aq. NaIO₄ / methanol / 1.25 h / 0 - 5 °C

With sodium periodate; acetic acid; In methanol; 1: Hydrolysis / 2: Oxidation;

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

Reference yield: 90.0%

1-benzyl-3S-benzyloxy-4R-[1'R,2'S-O-isopropylidene-3-oxo]propyl-azetidin-2-one (146467-05-2) → 1-benzyl-3S-benzyloxy-4R-[1'R,2'R-O-isopropylidene-3'-hydroxy]propyl-azetidin-2-one (146467-06-3)

Guidance literature:

With sodium tetrahydroborate; In methanol;

DOI:10.1021/jo00054a007

upstream raw materials:

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

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

Downstream raw materials:

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

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

(2S,3S)-3-Amino-3-((4R,5R)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-propane-1,2-diol

(2R,3R-O-isopropylidene)-4S-(N-benzylamino)-5R,6-dihydroxyhexyl-triphenylmethyl ether

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