(4R,5S)-3-((2R,3S)-6-Benzyloxy-3-hydroxy-2-methyl-hexanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Base Information

Chemical Name:(4R,5S)-3-((2R,3S)-6-Benzyloxy-3-hydroxy-2-methyl-hexanoyl)-4-methyl-5-phenyl-oxazolidin-2-one
CAS No.:852244-89-4
Molecular Formula:C₂₄H₂₉NO₅
Molecular Weight:411.498
Hs Code.:

Synonyms:(4R,5S)-3-((2R,3S)-6-Benzyloxy-3-hydroxy-2-methyl-hexanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

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Chemical Property of (4R,5S)-3-((2R,3S)-6-Benzyloxy-3-hydroxy-2-methyl-hexanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

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Technology Process of (4R,5S)-3-((2R,3S)-6-Benzyloxy-3-hydroxy-2-methyl-hexanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

There total 1 articles about (4R,5S)-3-((2R,3S)-6-Benzyloxy-3-hydroxy-2-methyl-hexanoyl)-4-methyl-5-phenyl-oxazolidin-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: 83.0%

: 5470-84-8
4-benzyloxybutanal

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

: 852244-89-4
(4R,5S)-3-((2R,3S)-6-Benzyloxy-3-hydroxy-2-methyl-hexanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: (4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at 0 ℃; for 1h;

4-benzyloxybutanal; In dichloromethane; at -78 - 20 ℃; for 2h;

With dihydrogen peroxide; In methanol; water; at 0 ℃; for 1h;
DOI:10.1021/ol0504291

Reference yield:

: 852244-89-4
(4R,5S)-3-((2R,3S)-6-Benzyloxy-3-hydroxy-2-methyl-hexanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

: (2R,3S)-3-{(2S,5S,7S)-7-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-1,6-dioxa-spiro[4.5]dec-2-yl}-2-methyl-oxirane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 13 steps

1.1: camphorsulfonic acid / CH₂Cl₂ / 24 h / 20 °C

2.1: 2.43 g / LiAlH₄ / tetrahydrofuran / 4 h / 0 °C

3.1: imidazole / dimethylformamide / 24 h / 20 °C

4.1: 0.57 g / W-2 Raney nickel; H₂ / ethanol / 24 h / 20 °C

5.1: 83 percent / I₂; Ph₃P; imidazole / benzene / 5 h / 20 °C

6.1: tert-butyllithium / pentane; diethyl ether / 1.17 h / -78 - 0 °C

6.2: 72 percent / pentane; diethyl ether / 3 h / 0 °C

7.1: 92 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 20 °C / pH 7

8.1: 95 percent / liithium p,p'-di-tert-butylbiphenyl / tetrahydrofuran / -78 °C

9.1: 92 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h

10.1: 86 percent / CH₂Cl₂ / 2 h / 20 °C

11.1: 89 percent / Dibal-H / CH₂Cl₂; hexane / 1 h / -40 °C

12.1: 95 percent / molecular sieves 4 Angstroem; L-(+)-diethyl tartrate; titanium isopropoxide / tert-butyl hydroperoxide / CH₂Cl₂ / 12 h / -23 °C

13.1: 98 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; lithium aluminium tetrahydride; lithium 4,4′-di(tert-butyl)biphenyl; diethyl (2R,3R)-tartrate; 4 A molecular sieve; W-2 Raney nickel; camphor-10-sulfonic acid; hydrogen; iodine; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert.-butylhydroperoxide; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; pentane; benzene; 10.1: Wittig reaction;
DOI:10.1021/ol0504291

Reference yield:

: 852244-89-4
(4R,5S)-3-((2R,3S)-6-Benzyloxy-3-hydroxy-2-methyl-hexanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

: 887001-90-3
(2S,5S,7S,1'S,2'S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(1',2'-epoxy-3'-hydroxy-2'-methylprop-1'-yl)-1,6-dioxaspiro[4.5]decane

Guidance literature:: Multi-step reaction with 12 steps

1.1: camphorsulfonic acid / CH₂Cl₂ / 24 h / 20 °C

2.1: 2.43 g / LiAlH₄ / tetrahydrofuran / 4 h / 0 °C

3.1: imidazole / dimethylformamide / 24 h / 20 °C

4.1: 0.57 g / W-2 Raney nickel; H₂ / ethanol / 24 h / 20 °C

5.1: 83 percent / I₂; Ph₃P; imidazole / benzene / 5 h / 20 °C

6.1: tert-butyllithium / pentane; diethyl ether / 1.17 h / -78 - 0 °C

6.2: 72 percent / pentane; diethyl ether / 3 h / 0 °C

7.1: 92 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 20 °C / pH 7

8.1: 95 percent / liithium p,p'-di-tert-butylbiphenyl / tetrahydrofuran / -78 °C

9.1: 92 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h

10.1: 86 percent / CH₂Cl₂ / 2 h / 20 °C

11.1: 89 percent / Dibal-H / CH₂Cl₂; hexane / 1 h / -40 °C

12.1: 95 percent / molecular sieves 4 Angstroem; L-(+)-diethyl tartrate; titanium isopropoxide / tert-butyl hydroperoxide / CH₂Cl₂ / 12 h / -23 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; lithium aluminium tetrahydride; lithium 4,4′-di(tert-butyl)biphenyl; diethyl (2R,3R)-tartrate; 4 A molecular sieve; W-2 Raney nickel; camphor-10-sulfonic acid; hydrogen; iodine; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert.-butylhydroperoxide; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; pentane; benzene; 10.1: Wittig reaction;
DOI:10.1021/ol0504291