tert-butyl-{(1S)-1-[(1S,5R)-5-methyl-2,7,8-trioxabicyclo[3.2.1]oct-1-yl}diphenylsilane

Base Information

Chemical Name:tert-butyl-{(1S)-1-[(1S,5R)-5-methyl-2,7,8-trioxabicyclo[3.2.1]oct-1-yl}diphenylsilane
CAS No.:199921-05-6
Molecular Formula:C₂₄H₃₂O₄Si
Molecular Weight:412.601
Hs Code.:

Synonyms:tert-butyl-{(1S)-1-[(1S,5R)-5-methyl-2,7,8-trioxabicyclo[3.2.1]oct-1-yl}diphenylsilane

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Chemical Property of tert-butyl-{(1S)-1-[(1S,5R)-5-methyl-2,7,8-trioxabicyclo[3.2.1]oct-1-yl}diphenylsilane

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Technology Process of tert-butyl-{(1S)-1-[(1S,5R)-5-methyl-2,7,8-trioxabicyclo[3.2.1]oct-1-yl}diphenylsilane

There total 4 articles about tert-butyl-{(1S)-1-[(1S,5R)-5-methyl-2,7,8-trioxabicyclo[3.2.1]oct-1-yl}diphenylsilane 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: 93.0%

: 199921-23-8
(2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid 2-[(2S)-2-methyloxiranyl]ethyl ester

: 199921-05-6
tert-butyl-{(1S)-1-[(1S,5R)-5-methyl-2,7,8-trioxabicyclo[3.2.1]oct-1-yl}diphenylsilane

Guidance literature:: With silver(I) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; zirconocene dichloride; In diethyl ether; dichloromethane; at -78 ℃; for 6h;
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

: 199921-05-6
tert-butyl-{(1S)-1-[(1S,5R)-5-methyl-2,7,8-trioxabicyclo[3.2.1]oct-1-yl}diphenylsilane

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

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

: 199921-05-6
tert-butyl-{(1S)-1-[(1S,5R)-5-methyl-2,7,8-trioxabicyclo[3.2.1]oct-1-yl}diphenylsilane

Guidance literature:: Multi-step reaction with 3 steps

1: 98 percent / triethylamine / CH₂Cl₂ / 0.25 h / -10 °C

2: 86 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.17 h / 22 °C

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

With silver(I) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zirconocene dichloride; In diethyl ether; dichloromethane; 1: sulfonylation / 2: Epoxidation / 3: Rearrangement;
DOI:10.1016/S0040-4020(97)01038-7