(2S)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-methylideneazetidine

Base Information

• Chemical Name: (2S)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-methylideneazetidine
• CAS No.: 1648572-35-3
• Molecular Formula: C₂₆H₃₅NO₃Si
• Molecular Weight: 437.654

Synonyms:(2S)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-methylideneazetidine

Chemical Property of (2S)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-methylideneazetidine

Chemical Property:

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Technology Process of (2S)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-methylideneazetidine

There total 4 articles about (2S)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-methylideneazetidine 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: 58.0%

dimethyltitanocene (1271-66-5) + (2R)-1-(tert-butyloxycarbonyl)-2-((tert-butyldiphenylsilyl)oxymethyl)-3-azetidinone (150943-17-2) → (2S)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-methylideneazetidine (1648572-35-3)

Guidance literature:

In toluene; at 80 ℃; for 2h; Inert atmosphere;

DOI:10.3762/bjoc.10.110

Reference yield: 50.0%

dimethyltitanocene (1271-66-5) + (2R)-1-(tert-butyloxycarbonyl)-2-((tert-butyldiphenylsilyl)oxymethyl)-3-azetidinone (150943-17-2) → (2S)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-methylideneazetidine (1648572-35-3) + (2S)-1-tert-butyloxycarbonyl-2-((tert-butyldiphenylsilyl)oxymethyl)-3,3-dimethyl-azetidine (1648572-36-4)

Guidance literature:

Inert atmosphere;

DOI:10.3762/bjoc.10.110

Reference yield: 36.0%

Tebbe's reagent + (2R)-1-(tert-butyloxycarbonyl)-2-((tert-butyldiphenylsilyl)oxymethyl)-3-azetidinone (150943-17-2) → (2S)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-methylideneazetidine (1648572-35-3)

Guidance literature:

With pyridine; In tetrahydrofuran; at -40 - 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.3762/bjoc.10.110

upstream raw materials:

(2R)-1-(tert-butyloxycarbonyl)-2-((tert-butyldiphenylsilyl)oxymethyl)-3-azetidinone

dimethyltitanocene

Methyltriphenylphosphonium bromide

Downstream raw materials:

5-tert-butyl 1-ethyl (1R,3R,4S)-4-(hydroxymethyl)-5-azaspiro[2.3]hexane-1,5-dicarboxylate

(1R,3R,4S)-5-(tert-butoxycarbonyl)-1-(ethoxycarbonyl)-5-azaspiro[2.3]hexane-4-carboxylic acid

5-tert-butyl 1-ethyl (1S,3S,4S)-4-(hydroxymethyl)-5-azaspiro[2.3]hexane-1,5-dicarboxylate

(1S,3S,4S)-5-(tert-butoxycarbonyl)-1-(ethoxycarbonyl)-5-azaspiro[2.3]hexane-4-carboxylic acid

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