(2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoic acid methoxy-methyl-amide

Base Information

Chemical Name:(2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoic acid methoxy-methyl-amide
CAS No.:160531-38-4
Molecular Formula:C₁₈H₂₉NO₄
Molecular Weight:323.433
Hs Code.:

Synonyms:(2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoic acid methoxy-methyl-amide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoic acid methoxy-methyl-amide

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Technology Process of (2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoic acid methoxy-methyl-amide

There total 10 articles about (2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoic acid methoxy-methyl-amide 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: 92.0%

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

: 160531-16-8
(S)-3-((2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoyl)-4-isopropyl-oxazolidin-2-one

: 160531-38-4
(2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoic acid methoxy-methyl-amide

Guidance literature:: With trimethylaluminum; In tetrahydrofuran; toluene; -19 deg C, 2 h; -6 deg C, 2 h;;
DOI:10.1016/S0040-4020(01)81206-0

Reference yield:

: 16451-50-6
(S)-4-methyl-pentane-1,3-diol

: 160531-38-4
(2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 13 h / Ambient temperature

2: 1.) 60percent NaH, 2.) concd HCl / 1.) DMF, 0 deg C to room temp., 2.5 h, 2.) MeOH, THF, 30 deg C, 4 h

3: 96 percent / (COCl)2, DMSO; Et₃N / CH₂Cl₂ / -78 deg C, 20 min; -78 to 0 deg C, 0 deg C, 15 min

4: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 50 min; -78 deg C, 30 min; 0 deg C, 1 h

5: 92 percent / Me₃Al / tetrahydrofuran; toluene / -19 deg C, 2 h; -6 deg C, 2 h;

With hydrogenchloride; dmap; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)81206-0

Reference yield:

: 160531-15-7
(S)-3-(benzyloxy)-4-methylpentanal

: 160531-38-4
(2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 50 min; -78 deg C, 30 min; 0 deg C, 1 h

2: 92 percent / Me₃Al / tetrahydrofuran; toluene / -19 deg C, 2 h; -6 deg C, 2 h;

With di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; triethylamine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)81206-0