(4R,5S)-3-[(2'R,3'S,6'R)-7'-tert-butyldimethylsilyloxy-3'-hydroxy-2',5'-dimethyl-1'-heptanoyl]-4-methyl-5-phenyl-2-oxazolidinone

Base Information

Chemical Name:(4R,5S)-3-[(2'R,3'S,6'R)-7'-tert-butyldimethylsilyloxy-3'-hydroxy-2',5'-dimethyl-1'-heptanoyl]-4-methyl-5-phenyl-2-oxazolidinone
CAS No.:856190-87-9
Molecular Formula:C₂₅H₄₁NO₅Si
Molecular Weight:463.69
Hs Code.:

Synonyms:(4R,5S)-3-[(2'R,3'S,6'R)-7'-tert-butyldimethylsilyloxy-3'-hydroxy-2',5'-dimethyl-1'-heptanoyl]-4-methyl-5-phenyl-2-oxazolidinone

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Chemical Property of (4R,5S)-3-[(2'R,3'S,6'R)-7'-tert-butyldimethylsilyloxy-3'-hydroxy-2',5'-dimethyl-1'-heptanoyl]-4-methyl-5-phenyl-2-oxazolidinone

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Technology Process of (4R,5S)-3-[(2'R,3'S,6'R)-7'-tert-butyldimethylsilyloxy-3'-hydroxy-2',5'-dimethyl-1'-heptanoyl]-4-methyl-5-phenyl-2-oxazolidinone

There total 3 articles about (4R,5S)-3-[(2'R,3'S,6'R)-7'-tert-butyldimethylsilyloxy-3'-hydroxy-2',5'-dimethyl-1'-heptanoyl]-4-methyl-5-phenyl-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: 94.0%

: 77877-20-4
(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one

: 152299-65-5
(4R)-5-(tert-butyldimethylsilanyloxy)-4-methylpentanal

: 856190-87-9
(4R,5S)-3-[(2'R,3'S,6'R)-7'-tert-butyldimethylsilyloxy-3'-hydroxy-2',5'-dimethyl-1'-heptanoyl]-4-methyl-5-phenyl-2-oxazolidinone

Guidance literature:: (4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one; (4R)-5-(tert-butyldimethylsilanyloxy)-4-methylpentanal; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -80 ℃; for 60h;

With phosphate buffer; dihydrogen peroxide; In methanol; dichloromethane; at 20 ℃; for 6h; pH=7.2;
DOI:10.1002/anie.200500174

Reference yield:

: 856191-02-1
(5R)-6-(tert-butyldimethylsilyloxy)-5-methylhex-1-ene

: 856190-87-9
(4R,5S)-3-[(2'R,3'S,6'R)-7'-tert-butyldimethylsilyloxy-3'-hydroxy-2',5'-dimethyl-1'-heptanoyl]-4-methyl-5-phenyl-2-oxazolidinone

Guidance literature:: Multi-step reaction with 2 steps

1.1: O₃ / CH₂Cl₂ / 0.25 h / -78 °C

1.2: 88 percent / PPh₃ / CH₂Cl₂ / 4.5 h / -78 - 20 °C

2.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 60 h / -80 °C

2.2: 94 percent / phosphate buffer; aq. H₂O₂ / CH₂Cl₂; methanol / 6 h / 20 °C / pH 7.2

With di-n-butylboryl trifluoromethanesulfonate; ozone; triethylamine; In dichloromethane;
DOI:10.1002/anie.200500174

Reference yield:

: 168335-78-2
(2S)-(+)-(tert-butyl-dimethyl)-(3-iodo-2-methyl-propoxy)-silane

: 856190-87-9
(4R,5S)-3-[(2'R,3'S,6'R)-7'-tert-butyldimethylsilyloxy-3'-hydroxy-2',5'-dimethyl-1'-heptanoyl]-4-methyl-5-phenyl-2-oxazolidinone

Guidance literature:: Multi-step reaction with 3 steps

1.1: 86 percent / tetrahydrofuran / 1 h / -15 - 20 °C

2.1: O₃ / CH₂Cl₂ / 0.25 h / -78 °C

2.2: 88 percent / PPh₃ / CH₂Cl₂ / 4.5 h / -78 - 20 °C

3.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 60 h / -80 °C

3.2: 94 percent / phosphate buffer; aq. H₂O₂ / CH₂Cl₂; methanol / 6 h / 20 °C / pH 7.2

With di-n-butylboryl trifluoromethanesulfonate; ozone; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1002/anie.200500174