[2S,2(1S),3R]-2-benzyloxy-4-(tert-butyldiphenylsilyl)oxy-3-methyl-2-(1-methylcyclohex-2-en-1-yl)butanoic acid

Base Information

Chemical Name:[2S,2(1S),3R]-2-benzyloxy-4-(tert-butyldiphenylsilyl)oxy-3-methyl-2-(1-methylcyclohex-2-en-1-yl)butanoic acid
CAS No.:1519887-23-0
Molecular Formula:C₃₅H₄₄O₄Si
Molecular Weight:556.817
Hs Code.:

Synonyms:[2S,2(1S),3R]-2-benzyloxy-4-(tert-butyldiphenylsilyl)oxy-3-methyl-2-(1-methylcyclohex-2-en-1-yl)butanoic acid

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Chemical Property of [2S,2(1S),3R]-2-benzyloxy-4-(tert-butyldiphenylsilyl)oxy-3-methyl-2-(1-methylcyclohex-2-en-1-yl)butanoic acid

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Technology Process of [2S,2(1S),3R]-2-benzyloxy-4-(tert-butyldiphenylsilyl)oxy-3-methyl-2-(1-methylcyclohex-2-en-1-yl)butanoic acid

There total 8 articles about [2S,2(1S),3R]-2-benzyloxy-4-(tert-butyldiphenylsilyl)oxy-3-methyl-2-(1-methylcyclohex-2-en-1-yl)butanoic acid 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: 48.0%

: 1519887-14-9
(R)-3-methylcyclohex-2-en-1-yl (2R,3R)-2-benzyloxy-4-(tert-butyldiphenylsilyl)oxy-3-methylbutanoate

: 1519887-23-0
[2S,2(1S),3R]-2-benzyloxy-4-(tert-butyldiphenylsilyl)oxy-3-methyl-2-(1-methylcyclohex-2-en-1-yl)butanoic acid

Guidance literature:: With chloro-trimethyl-silane; lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃; for 12h;
DOI:10.1021/jo402537u

Reference yield:

: 1519887-08-1
(2R,3R)-2-benzyloxy-4-(tert-butyldiphenylsilyl)oxy-3-methyl-1-butanal

: 1519887-23-0
[2S,2(1S),3R]-2-benzyloxy-4-(tert-butyldiphenylsilyl)oxy-3-methyl-2-(1-methylcyclohex-2-en-1-yl)butanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / tert-butyl alcohol; water / 3 h

2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 0 - 20 °C

3: chloro-trimethyl-silane; lithium diisopropyl amide / tetrahydrofuran / 12 h / -78 - 20 °C

With dmap; sodium chlorite; sodium dihydrogenphosphate; chloro-trimethyl-silane; 2-methyl-but-2-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo402537u

Reference yield:

: 1519887-10-5
(2R,3R)-2-benzyloxy-4-(tert-butyldiphenylsilyl)oxy-3-methyl-1-butanal

: 1519887-23-0
[2S,2(1S),3R]-2-benzyloxy-4-(tert-butyldiphenylsilyl)oxy-3-methyl-2-(1-methylcyclohex-2-en-1-yl)butanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 0 - 20 °C

2: chloro-trimethyl-silane; lithium diisopropyl amide / tetrahydrofuran / 12 h / -78 - 20 °C

With dmap; chloro-trimethyl-silane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo402537u