(3R,4S,5R)-6-<(tert-Butyldiphenylsilyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-1-(2'-thiazolyl)-1-hexanone

Base Information

Chemical Name:(3R,4S,5R)-6-<(tert-Butyldiphenylsilyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-1-(2'-thiazolyl)-1-hexanone
CAS No.:172293-75-3
Molecular Formula:C₃₄H₅₅NO₅SSi₄
Molecular Weight:702.222
Hs Code.:

Synonyms:(3R,4S,5R)-6-<(tert-Butyldiphenylsilyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-1-(2'-thiazolyl)-1-hexanone

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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 (3R,4S,5R)-6-<(tert-Butyldiphenylsilyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-1-(2'-thiazolyl)-1-hexanone

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Technology Process of (3R,4S,5R)-6-<(tert-Butyldiphenylsilyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-1-(2'-thiazolyl)-1-hexanone

There total 4 articles about (3R,4S,5R)-6-<(tert-Butyldiphenylsilyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-1-(2'-thiazolyl)-1-hexanone 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: 87.0%

: 288-47-1
1,3-thiazole

: 172293-73-1
(3R,4S,5R)-6-<(tert-Butyldiphenylsilyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-N-methoxy-N-methylhexanamide

: 172293-75-3
(3R,4S,5R)-6-<(tert-Butyldiphenylsilyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-1-(2'-thiazolyl)-1-hexanone

Guidance literature:: With n-butyllithium; In diethyl ether; at -78 ℃; 1.) 10 min, 2.) 15 min;
DOI:10.1021/jo00127a047

Reference yield:

: 153321-80-3
(3R,4R,5R)-tert-butyl <6-(tert-butyldiphenylsilyloxy)-4,5-epoxy-3-hydroxy>hexanoate

: 172293-75-3
(3R,4S,5R)-6-<(tert-Butyldiphenylsilyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-1-(2'-thiazolyl)-1-hexanone

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / Zn, (CH₃)3SiCl / CH₂Cl₂ / 0.03 h / Ambient temperature

2: AlMe₃ / CH₂Cl₂ / Ambient temperature; 1.) 30 min, 2.) 12 h

3: HMDS, pyridine / 3 h / Ambient temperature

4: 87 percent / n-BuLi / diethyl ether / -78 °C / 1.) 10 min, 2.) 15 min

With pyridine; n-butyllithium; chloro-trimethyl-silane; trimethylaluminum; 1,1,1,3,3,3-hexamethyl-disilazane; zinc; In diethyl ether; dichloromethane;
DOI:10.1021/jo00127a047

Reference yield:

: 172293-71-9
(4R,5S,1'R)-5-<2'-<(tert-Butyldiphenylsilyl)oxy>-1'-hydroxyethyl>-4-hydroxy-2-oxo-1-oxacyclopentane

: 172293-75-3
(3R,4S,5R)-6-<(tert-Butyldiphenylsilyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-1-(2'-thiazolyl)-1-hexanone

Guidance literature:: Multi-step reaction with 3 steps

1: AlMe₃ / CH₂Cl₂ / Ambient temperature; 1.) 30 min, 2.) 12 h

2: HMDS, pyridine / 3 h / Ambient temperature

3: 87 percent / n-BuLi / diethyl ether / -78 °C / 1.) 10 min, 2.) 15 min

With pyridine; n-butyllithium; trimethylaluminum; 1,1,1,3,3,3-hexamethyl-disilazane; In diethyl ether; dichloromethane;
DOI:10.1021/jo00127a047