(3S,4R)-4-<<4-(Benzyloxy)-2-methyl-4-nitro-3(Z)-buten-2-yl>thio>-1-(tert-butyldimethylsilyl)-3-(trimethylsilyl)-2-azetidinone

Base Information

Chemical Name:(3S,4R)-4-<<4-(Benzyloxy)-2-methyl-4-nitro-3(Z)-buten-2-yl>thio>-1-(tert-butyldimethylsilyl)-3-(trimethylsilyl)-2-azetidinone
CAS No.:124831-32-9
Molecular Formula:C₂₄H₄₀N₂O₄SSi₂
Molecular Weight:508.83
Hs Code.:

Synonyms:(3S,4R)-4-<<4-(Benzyloxy)-2-methyl-4-nitro-3(Z)-buten-2-yl>thio>-1-(tert-butyldimethylsilyl)-3-(trimethylsilyl)-2-azetidinone

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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 (3S,4R)-4-<<4-(Benzyloxy)-2-methyl-4-nitro-3(Z)-buten-2-yl>thio>-1-(tert-butyldimethylsilyl)-3-(trimethylsilyl)-2-azetidinone

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (3S,4R)-4-<<4-(Benzyloxy)-2-methyl-4-nitro-3(Z)-buten-2-yl>thio>-1-(tert-butyldimethylsilyl)-3-(trimethylsilyl)-2-azetidinone

There total 5 articles about (3S,4R)-4-<<4-(Benzyloxy)-2-methyl-4-nitro-3(Z)-buten-2-yl>thio>-1-(tert-butyldimethylsilyl)-3-(trimethylsilyl)-2-azetidinone 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%

: 128971-81-3
(3S,4R)-4-<<4-(Benzyloxy)-3-hydroxy-2-methyl-4-nitro-2-butyl>thio>-1-(tert-butyldimethylsilyl)-3-(trimethylsilyl)-2-azetidinone

: 124831-32-9
(3S,4R)-4-<<4-(Benzyloxy)-2-methyl-4-nitro-3(Z)-buten-2-yl>thio>-1-(tert-butyldimethylsilyl)-3-(trimethylsilyl)-2-azetidinone

Guidance literature:: With triethylamine; acetyl chloride; at 0 ℃; for 20h;
DOI:10.1021/jo00304a024

Reference yield:

: 128971-79-9
(3S,4R)-4-<(2-Methyl-3-buten-2-yl)thio>-3-(trimethylsilyl)-2-azetidinone

: 124831-32-9
(3S,4R)-4-<<4-(Benzyloxy)-2-methyl-4-nitro-3(Z)-buten-2-yl>thio>-1-(tert-butyldimethylsilyl)-3-(trimethylsilyl)-2-azetidinone

Guidance literature:: Multi-step reaction with 4 steps

1: 83 percent / i-Pr₂NEt, N,N-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / Ambient temperature

2: 1) O₃, 2) Me₂S / 1) CH₂Cl₂, -78 deg C, 2) 0 deg C, 15 min

3: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h

4: 72 percent / Et₃N, acetyl chloride / 20 h / 0 °C

With dmap; dimethylsulfide; potassium tert-butylate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; In dichloromethane;
DOI:10.1021/jo00304a024

Reference yield:

: 128971-80-2
(3S,4R)-1-(tert-Butyldimethylsilyl)-4-<(2-methyl-3-buten-2-yl)thio>-3-(trimethylsilyl)-2-azetidinone

: 124831-32-9
(3S,4R)-4-<<4-(Benzyloxy)-2-methyl-4-nitro-3(Z)-buten-2-yl>thio>-1-(tert-butyldimethylsilyl)-3-(trimethylsilyl)-2-azetidinone

Guidance literature:: Multi-step reaction with 3 steps

1: 1) O₃, 2) Me₂S / 1) CH₂Cl₂, -78 deg C, 2) 0 deg C, 15 min

2: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h

3: 72 percent / Et₃N, acetyl chloride / 20 h / 0 °C

With dimethylsulfide; potassium tert-butylate; ozone; triethylamine; acetyl chloride;
DOI:10.1021/jo00304a024