(4S,5R)-5-(benzyloxy)-8-(tert-butyldimethylsiloxy)-4-((2'-methoxyphenyl)amino)-2-octanone

Base Information

Chemical Name:(4S,5R)-5-(benzyloxy)-8-(tert-butyldimethylsiloxy)-4-((2'-methoxyphenyl)amino)-2-octanone
CAS No.:223676-02-6
Molecular Formula:C₂₈H₄₃NO₄Si
Molecular Weight:485.739
Hs Code.:

Synonyms:(4S,5R)-5-(benzyloxy)-8-(tert-butyldimethylsiloxy)-4-((2'-methoxyphenyl)amino)-2-octanone

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Chemical Property of (4S,5R)-5-(benzyloxy)-8-(tert-butyldimethylsiloxy)-4-((2'-methoxyphenyl)amino)-2-octanone

Chemical Property:

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Technology Process of (4S,5R)-5-(benzyloxy)-8-(tert-butyldimethylsiloxy)-4-((2'-methoxyphenyl)amino)-2-octanone

There total 13 articles about (4S,5R)-5-(benzyloxy)-8-(tert-butyldimethylsiloxy)-4-((2'-methoxyphenyl)amino)-2-octanone 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:

: 89922-82-7
3-(tert-butyldimethylsilanyloxy)propionaldehyde

: 223676-02-6
(4S,5R)-5-(benzyloxy)-8-(tert-butyldimethylsiloxy)-4-((2'-methoxyphenyl)amino)-2-octanone

Guidance literature:: Multi-step reaction with 6 steps

1: (R)-1-methyl-2-(5,6,7,8-tetrahydro-1-naphthylaminomethyl)...; Sn(OTf)2; SnO / various solvent(s) / 2 h / -78 °C

2: 88 percent / tetrahydrofuran / 1.5 h / Heating

3: 86 percent / Bu₃SnH; AIBN / toluene / 6 h / Heating

4: 75 percent / DIBAL / hexane; CH₂Cl₂ / 1 h / -78 °C

5: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6: Yb(OTf)3 / H₂O; tetrahydrofuran / 0.75 h / 0 °C

With tin(II) trifluoromethanesulfonate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); (R)-1-methyl-2-(5,6,7,8-tetrahydro-1-naphthylaminomethyl)..; tri-n-butyl-tin hydride; tin(II) oxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; hexane; dichloromethane; water; toluene; 1: Addition / 2: Substitution / 3: Reduction / 4: Reduction / 5: Oxidation / 6: Condensation;
DOI:10.1021/jo990877k

Reference yield:

: 223676-04-8
(R)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)pentanol

: 223676-02-6
(4S,5R)-5-(benzyloxy)-8-(tert-butyldimethylsiloxy)-4-((2'-methoxyphenyl)amino)-2-octanone

Guidance literature:: Multi-step reaction with 2 steps

1: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: Yb(OTf)3 / H₂O; tetrahydrofuran / 0.75 h / 0 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; water; 1: Oxidation / 2: Condensation;
DOI:10.1021/jo990877k

Reference yield:

: 223675-82-9
(2R,3S)-phenyl 2-(benzyloxy)-5-(tert-butyldimethylsiloxy)-3-hydroxypentanoate

: 223676-02-6
(4S,5R)-5-(benzyloxy)-8-(tert-butyldimethylsiloxy)-4-((2'-methoxyphenyl)amino)-2-octanone

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / tetrahydrofuran / 1.5 h / Heating

2: 86 percent / Bu₃SnH; AIBN / toluene / 6 h / Heating

3: 75 percent / DIBAL / hexane; CH₂Cl₂ / 1 h / -78 °C

4: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5: Yb(OTf)3 / H₂O; tetrahydrofuran / 0.75 h / 0 °C

With oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; hexane; dichloromethane; water; toluene; 1: Substitution / 2: Reduction / 3: Reduction / 4: Oxidation / 5: Condensation;
DOI:10.1021/jo990877k