(2R,3S,4R,5S)-6-benzyloxy-2,4-dimethyl-3,5-bis(triethylsilyloxy)-N-methoxy-N-methylhexanamide

Base Information

Chemical Name:(2R,3S,4R,5S)-6-benzyloxy-2,4-dimethyl-3,5-bis(triethylsilyloxy)-N-methoxy-N-methylhexanamide
CAS No.:614759-29-4
Molecular Formula:C₂₉H₅₅NO₅Si₂
Molecular Weight:553.93
Hs Code.:

Synonyms:(2R,3S,4R,5S)-6-benzyloxy-2,4-dimethyl-3,5-bis(triethylsilyloxy)-N-methoxy-N-methylhexanamide

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Chemical Property of (2R,3S,4R,5S)-6-benzyloxy-2,4-dimethyl-3,5-bis(triethylsilyloxy)-N-methoxy-N-methylhexanamide

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Technology Process of (2R,3S,4R,5S)-6-benzyloxy-2,4-dimethyl-3,5-bis(triethylsilyloxy)-N-methoxy-N-methylhexanamide

There total 4 articles about (2R,3S,4R,5S)-6-benzyloxy-2,4-dimethyl-3,5-bis(triethylsilyloxy)-N-methoxy-N-methylhexanamide 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: 59.0%

: 994-30-9
triethylsilyl chloride

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 614759-28-3
[[3-(2R,3S,4R,5S),4R]-3-(6-benzyloxy-3,5-dihydroxy-2,4-dimethyl-1-oxohexyl)-4-(phenylmethyl)]-2-oxazolidinone

: 614759-29-4
(2R,3S,4R,5S)-6-benzyloxy-2,4-dimethyl-3,5-bis(triethylsilyloxy)-N-methoxy-N-methylhexanamide

: C₃₉H₆₆N₂O₇Si₂

Guidance literature:: N,O-dimethylhydroxylamine*hydrochloride; With trimethylaluminum; In dichloromethane; toluene; at 0 - 20 ℃;

[[3-(2R,3S,4R,5S),4R]-3-(6-benzyloxy-3,5-dihydroxy-2,4-dimethyl-1-oxohexyl)-4-(phenylmethyl)]-2-oxazolidinone; In dichloromethane; toluene; at -45 ℃; for 5h;

triethylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; Further stages.;
DOI:10.1039/b302460a

Reference yield:

: 60656-87-3
benzyloxyacetoaldehyde

: 614759-29-4
(2R,3S,4R,5S)-6-benzyloxy-2,4-dimethyl-3,5-bis(triethylsilyloxy)-N-methoxy-N-methylhexanamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: Sn(OTf)2; NEt₃ / CH₂Cl₂ / 1 h / -20 °C

1.2: 77 percent / CH₂Cl₂ / 1.5 h / -78 °C

2.1: 91 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile / -40 - 20 °C

3.1: AlMe₃ / CH₂Cl₂; toluene / 0 - 20 °C

3.2: CH₂Cl₂; toluene / 5 h / -45 °C

3.3: 59 percent / imidazole / dimethylformamide / 20 °C

With tin(II) trifluoromethanesulfonate; trimethylaluminum; triethylamine; tetramethylammonium triacetoxyborohydride; In dichloromethane; acetic acid; toluene; acetonitrile; 1.2: Evans aldol reaction;
DOI:10.1039/b302460a

Reference yield:

: 101712-01-0,141423-22-5,141423-21-4
(R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-methylpentane-1,3-dione

: 614759-29-4
(2R,3S,4R,5S)-6-benzyloxy-2,4-dimethyl-3,5-bis(triethylsilyloxy)-N-methoxy-N-methylhexanamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: Sn(OTf)2; NEt₃ / CH₂Cl₂ / 1 h / -20 °C

1.2: 77 percent / CH₂Cl₂ / 1.5 h / -78 °C

2.1: 91 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile / -40 - 20 °C

3.1: AlMe₃ / CH₂Cl₂; toluene / 0 - 20 °C

3.2: CH₂Cl₂; toluene / 5 h / -45 °C

3.3: 59 percent / imidazole / dimethylformamide / 20 °C

With tin(II) trifluoromethanesulfonate; trimethylaluminum; triethylamine; tetramethylammonium triacetoxyborohydride; In dichloromethane; acetic acid; toluene; acetonitrile; 1.2: Evans aldol reaction;
DOI:10.1039/b302460a