[[3-(2S,3R,4S,5R)-4S]-3-(5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4,6-trimethyl-1-oxohept-6-enyl)-4-(phenylmethyl)]-2-oxazolidinone

Base Information

Chemical Name:[[3-(2S,3R,4S,5R)-4S]-3-(5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4,6-trimethyl-1-oxohept-6-enyl)-4-(phenylmethyl)]-2-oxazolidinone
CAS No.:1415730-32-3
Molecular Formula:C₂₆H₄₁NO₅Si
Molecular Weight:475.701
Hs Code.:

Synonyms:[[3-(2S,3R,4S,5R)-4S]-3-(5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4,6-trimethyl-1-oxohept-6-enyl)-4-(phenylmethyl)]-2-oxazolidinone

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Chemical Property of [[3-(2S,3R,4S,5R)-4S]-3-(5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4,6-trimethyl-1-oxohept-6-enyl)-4-(phenylmethyl)]-2-oxazolidinone

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Technology Process of [[3-(2S,3R,4S,5R)-4S]-3-(5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4,6-trimethyl-1-oxohept-6-enyl)-4-(phenylmethyl)]-2-oxazolidinone

There total 2 articles about [[3-(2S,3R,4S,5R)-4S]-3-(5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4,6-trimethyl-1-oxohept-6-enyl)-4-(phenylmethyl)]-2-oxazolidinone 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: 65.0%

: 131685-53-5,101711-78-8
(S)-4-benzyl-3-propionyl-2-oxazolidinone

: 171013-57-3
(2R,3R)-3-(tert-butyldimethylsilyloxy)-2,4-dimethylpent-4-enal

: 1415730-32-3
[[3-(2S,3R,4S,5R)-4S]-3-(5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4,6-trimethyl-1-oxohept-6-enyl)-4-(phenylmethyl)]-2-oxazolidinone

Guidance literature:: (S)-4-benzyl-3-propionyl-2-oxazolidinone; With di-n-butylboryl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

With triethylamine; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

(2R,3R)-3-(tert-butyldimethylsilyloxy)-2,4-dimethylpent-4-enal; In dichloromethane; at -78 - 0 ℃; for 4.5h; Inert atmosphere;
DOI:10.1016/j.tet.2012.10.008

Reference yield:

: 186885-60-9
[[3-(2R,3R)-4R]-3-(3-hydroxy-2,4-dimethyl-1-oxopent-4-enyl)-4-(phenylmethyl)]-2-oxazolidinone

: 1415730-32-3
[[3-(2S,3R,4S,5R)-4S]-3-(5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4,6-trimethyl-1-oxohept-6-enyl)-4-(phenylmethyl)]-2-oxazolidinone

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 5 h / -78 °C / Inert atmosphere

2.1: lithium borohydride; ethanol / tetrahydrofuran; diethyl ether / 4 h / -10 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 - 0 °C / Inert atmosphere

4.1: di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

4.2: 0.5 h / 0 °C / Inert atmosphere

4.3: 4.5 h / -78 - 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; lithium borohydride; oxalyl dichloride; ethanol; di-n-butylboryl trifluoromethanesulfonate; dimethyl sulfoxide; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/j.tet.2012.10.008

Reference yield: 94.0%

: 1415730-32-3
[[3-(2S,3R,4S,5R)-4S]-3-(5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4,6-trimethyl-1-oxohept-6-enyl)-4-(phenylmethyl)]-2-oxazolidinone

: 124356-87-2
[[3-(2S,3R,4S,5R)-4S]-3-(3,5-dihydroxy-2,4,6-trimethyl-1-oxohept-6-enyl)-4-(phenylmethyl)]-2-oxazolidinone

Guidance literature:: With pyridine; water; pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 120h; Inert atmosphere;
DOI:10.1016/j.tet.2012.10.008