(3R,4S)-3-[(1R)-1-tert-butyldimethylsiloxyethyl]-4-(3-tert-butyldimethylsiloxy-3-phenyl-2-oxopropyl)azetidin-2-one

Base Information

Chemical Name:(3R,4S)-3-[(1R)-1-tert-butyldimethylsiloxyethyl]-4-(3-tert-butyldimethylsiloxy-3-phenyl-2-oxopropyl)azetidin-2-one
CAS No.:189072-85-3
Molecular Formula:C₂₆H₄₅NO₄Si₂
Molecular Weight:491.819
Hs Code.:

Synonyms:(3R,4S)-3-[(1R)-1-tert-butyldimethylsiloxyethyl]-4-(3-tert-butyldimethylsiloxy-3-phenyl-2-oxopropyl)azetidin-2-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R,4S)-3-[(1R)-1-tert-butyldimethylsiloxyethyl]-4-(3-tert-butyldimethylsiloxy-3-phenyl-2-oxopropyl)azetidin-2-one

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Technology Process of (3R,4S)-3-[(1R)-1-tert-butyldimethylsiloxyethyl]-4-(3-tert-butyldimethylsiloxy-3-phenyl-2-oxopropyl)azetidin-2-one

There total 1 articles about (3R,4S)-3-[(1R)-1-tert-butyldimethylsiloxyethyl]-4-(3-tert-butyldimethylsiloxy-3-phenyl-2-oxopropyl)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: 42.0%

: 76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1
(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

: 163799-44-8
1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-phenyl-2-propanone

: 189072-85-3
(3R,4S)-3-[(1R)-1-tert-butyldimethylsiloxyethyl]-4-(3-tert-butyldimethylsiloxy-3-phenyl-2-oxopropyl)azetidin-2-one

Guidance literature:: With LiH(CH₃)2Si; In tetrahydrofuran; at -78 ℃; for 18h; under Ar; quenching by satd. NH₄Cl; extn. with Et₂O; purification by flash chromy. on SiO₂;
DOI:10.7164/antibiotics.50.237

Reference yield: 66.0%

: 92771-89-6
p-methoxybenzyl glyoxylate monohydrate

: 603-35-0
triphenylphosphine

: 189072-85-3
(3R,4S)-3-[(1R)-1-tert-butyldimethylsiloxyethyl]-4-(3-tert-butyldimethylsiloxy-3-phenyl-2-oxopropyl)azetidin-2-one

: (3R,4S)-3-{[(1R)-1-tert-butyldimethylsiloxy]ethyl}-1-[p-methoxycarbonyl(triphenylphosphoranylidene)methyl]-4-(3-tertbutyldimethylsiloxy-3-phenyl-2-oxopropyl)azetidin-2-one

Guidance literature:: With 2,6-dimethylpyridine; thionyl chloride; triethylamine; In tetrahydrofuran; 1,4-dioxane; benzene; glyoxylate refluxing in C₆H₆; Et₃N and azetidinone adding, stirring under Ar; treating with 2,6-luidine, SOCL₂ and Ph₃P;
DOI:10.7164/antibiotics.50.237

Reference yield:

: 189072-85-3
(3R,4S)-3-[(1R)-1-tert-butyldimethylsiloxyethyl]-4-(3-tert-butyldimethylsiloxy-3-phenyl-2-oxopropyl)azetidin-2-one

: (3R,4S)-3-[(1R)-1-hydroxyethyl]-1-[p-methoxycarbonyl(triphenylphosphoranylidene)methyl]-4-(3-tertbutyldimethylsiloxy-3-phenyl-2-oxopropyl)azetidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 66 percent / Et₃N; SOCl₂; 2,6-lutidine / benzene; tetrahydrofuran; dioxane / glyoxylate refluxing in C₆H₆; Et₃N and azetidinone adding, stirring under Ar; treating with 2,6-luidine, SOCL₂ and Ph₃P

2: 66 percent / HCl / methanol / 16 h / treating with 2 M HCl, adjusting to pH 6 with satd. NaHCO₃; extn. with EtOAc; purification by flash chromy. on SiO₂

With 2,6-dimethylpyridine; hydrogenchloride; thionyl chloride; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; benzene; 1: Substitution / 2: Hydrolysis;
DOI:10.7164/antibiotics.50.237