(3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'S,6'S)-2'-(t-butyldimethylsilyloxymethyl)cyclohexanone-6'-yl]azetidin-2-one

Base Information

• Chemical Name: (3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'S,6'S)-2'-(t-butyldimethylsilyloxymethyl)cyclohexanone-6'-yl]azetidin-2-one
• CAS No.: 299177-87-0
• Molecular Formula: C₂₄H₄₇NO₄Si₂
• Molecular Weight: 469.812

Synonyms:(3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'S,6'S)-2'-(t-butyldimethylsilyloxymethyl)cyclohexanone-6'-yl]azetidin-2-one

Chemical Property of (3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'S,6'S)-2'-(t-butyldimethylsilyloxymethyl)cyclohexanone-6'-yl]azetidin-2-one

Chemical Property:

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Technology Process of (3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'S,6'S)-2'-(t-butyldimethylsilyloxymethyl)cyclohexanone-6'-yl]azetidin-2-one

There total 1 articles about (3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'S,6'S)-2'-(t-butyldimethylsilyloxymethyl)cyclohexanone-6'-yl]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: 45.0%

(3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-1-trimethylsilyl-2-azetidinone (86978-81-6) + 6-[(tert-butyldimethylsilyloxy)methyl]-1-trimethylsilyloxy-1-cyclohexene (145386-69-2) → (3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'S,6'S)-2'-(t-butyldimethylsilyloxymethyl)cyclohexanone-6'-yl]azetidin-2-one (299177-87-0) + (3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'R,6'R)-2'-(t-butyldimethylsilyloxymethyl)cyclohexanone-6'-yl]azetidin-2-one (135297-29-9)

Guidance literature:

(3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-1-trimethylsilyl-2-azetidinone; 6-[(tert-butyldimethylsilyloxy)methyl]-1-trimethylsilyloxy-1-cyclohexene; With zinc(II) chloride; In dichloromethane; at 20 ℃; for 3h;

With silica gel; In methanol; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(00)00413-0

Reference yield:

allyl oxalyl chloride (74503-07-4) + (3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(2'S,6'S)-2'-(t-butyldimethylsilyloxymethyl)cyclohexanone-6'-yl]azetidin-2-one (299177-87-0) → {(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(1S,3S)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-cyclohexyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid allyl ester (299177-88-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(00)00413-0

upstream raw materials:

(3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-1-trimethylsilyl-2-azetidinone

6-[(tert-butyldimethylsilyloxy)methyl]-1-trimethylsilyloxy-1-cyclohexene

Downstream raw materials:

{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(1S,3S)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-cyclohexyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid allyl ester

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