(3R,4R)-4-(benzyloxycarbonylmethyl)-1-(tert-butyldimethylsilyl)-3-ethylazetidin-2-one

Base Information

• Chemical Name: (3R,4R)-4-(benzyloxycarbonylmethyl)-1-(tert-butyldimethylsilyl)-3-ethylazetidin-2-one
• CAS No.: 141195-51-9
• Molecular Formula: C₂₀H₃₁NO₃Si
• Molecular Weight: 361.557

Synonyms:(3R,4R)-4-(benzyloxycarbonylmethyl)-1-(tert-butyldimethylsilyl)-3-ethylazetidin-2-one

Chemical Property of (3R,4R)-4-(benzyloxycarbonylmethyl)-1-(tert-butyldimethylsilyl)-3-ethylazetidin-2-one

Chemical Property:

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Technology Process of (3R,4R)-4-(benzyloxycarbonylmethyl)-1-(tert-butyldimethylsilyl)-3-ethylazetidin-2-one

There total 14 articles about (3R,4R)-4-(benzyloxycarbonylmethyl)-1-(tert-butyldimethylsilyl)-3-ethylazetidin-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: 98.0%

(3R*,4R*)-N-(tert-butyldimethylsilyl)-3-ethyl-4-(methoxycarbonylmethyl)azetidin-2-one (86400-33-1,125606-73-7,125606-77-1,129329-74-4,129329-75-5) + benzyl alcohol (100-51-6,185532-71-2) → (3R*,4R*)-4-(benzyloxycarbonylmethyl)-N-(tert-butyldimethylsilyl)-3-ethylazetidin-2-one (125606-80-6,137623-37-1,138513-13-0,141195-51-9)

Guidance literature:

With titanium(IV) isopropylate; at 80 ℃; for 2h;

DOI:10.1248/cpb.39.2225

Reference yield: 76.0%

(2R,3R)-1-tert-butyldimethylsilyl-3-ethyl-4-oxo-2-azetidineacetic acid (93552-94-4) + benzyl chloroformate (501-53-1,94274-21-2) → (3R,4R)-4-(benzyloxycarbonylmethyl)-1-(tert-butyldimethylsilyl)-3-ethylazetidin-2-one (141195-51-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 1h;

DOI:10.1016/0040-4020(96)00849-6

Reference yield: 43.0%

1-benzyloxy-1-(trimethylsilyloxy)ethylene (81171-44-0) + (3S)-1-(tert-butyldimethylsilyl)-3-ethyl-4-(phenylsulfinyl)azetidin-2-one (129329-64-2,129389-66-8,141195-48-4,141195-49-5,141195-50-8,141269-29-6) → (3R,4R)-4-(benzyloxycarbonylmethyl)-1-(tert-butyldimethylsilyl)-3-ethylazetidin-2-one (141195-51-9)

Guidance literature:

With zinc(II) iodide; In acetonitrile; for 3h; Ambient temperature;

DOI:10.1248/cpb.40.12

upstream raw materials:

1-benzyloxy-1-(trimethylsilyloxy)ethylene

(3S)-1-(tert-butyldimethylsilyl)-3-ethyl-4-(phenylsulfinyl)azetidin-2-one

(2R,3R)-1-tert-butyldimethylsilyl-3-ethyl-4-oxo-2-azetidineacetic acid

benzyl chloroformate

Downstream raw materials:

(3R*,4R*)-4-(benzyloxycarbonylmethyl)-3-ethylazetidin-2-one

(3R,4R)-4-(benzyloxycarbonylmethyl)-3-ethylazetidin-2-one

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