(2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid 2-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]ethyl ester

Base Information

Chemical Name:(2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid 2-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]ethyl ester
CAS No.:199921-26-1
Molecular Formula:C₂₇H₃₈O₅Si
Molecular Weight:470.681
Hs Code.:

Synonyms:(2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid 2-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]ethyl ester

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Chemical Property of (2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid 2-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]ethyl ester

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Technology Process of (2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid 2-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]ethyl ester

There total 1 articles about (2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid 2-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]ethyl ester 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: 69.0%

: 64018-43-5
2-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]ethanol

: 125941-75-5
(S)-2-[(1,1-dimethylethyl)diphenylsilyl]oxypropanoic acid

: 199921-26-1
(2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid 2-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]ethyl ester

Guidance literature:: With dmap; 4-(dimethylamino)pyridine hydrochloride; dicyclohexyl-carbodiimide; In dichloromethane; at 22 ℃; for 20.5h;
DOI:10.1016/S0040-4020(97)01038-7

Reference yield: 52.0%

: 199921-26-1
(2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid 2-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]ethyl ester

: 199921-27-2
(2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid (3S)-3,4-dihydroxy-3-methylbutyl ester

Guidance literature:: With sulfuric acid; In tetrahydrofuran; at 50 ℃; for 4h;
DOI:10.1016/S0040-4020(97)01038-7

Reference yield:

: 199921-26-1
(2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid 2-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]ethyl ester

: 125941-75-5
(S)-2-[(1,1-dimethylethyl)diphenylsilyl]oxypropanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 52 percent / aq. H₂SO₄ / tetrahydrofuran / 4 h / 50 °C

2: 98 percent / triethylamine / CH₂Cl₂ / 0.25 h / -10 °C

3: 86 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.17 h / 22 °C

4: 93 percent / silver tetrakis[3,5-bis(trifluoromethyl)phenyl]borate / zirconocene dichloride / CH₂Cl₂; diethyl ether / 6 h / -78 °C

5: zirconocene dichloride; silver perchlorate; 4-methyl-1-propyl-2,6,7-trioxabicyclo[2.2.2]octane / CH₂Cl₂ / 1 h / 0 - 22 °C

6: 17 mg / aq. LiOH / tetrahydrofuran / 4 h / 22 °C

With silver(I) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; lithium hydroxide; zirconocene dichloride; sulfuric acid; silver perchlorate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 4-Methyl-1-propyl-2,6,7-trioxabicyclo<2.2.2>octane; zirconocene dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Ring cleavage / 2: sulfonylation / 3: Epoxidation / 4: Rearrangement / 5: Rearrangement / 6: Hydrolysis;
DOI:10.1016/S0040-4020(97)01038-7