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

Base Information

Chemical Name:(4R,5S,1'R)-5-<2'-<(tert-Butyldiphenylsilyl)oxy>-1'-hydroxyethyl>-4-hydroxy-2-oxo-1-oxacyclopentane
CAS No.:172293-71-9
Molecular Formula:C₂₂H₂₈O₅Si
Molecular Weight:400.547
Hs Code.:

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

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Chemical Property of (4R,5S,1'R)-5-<2'-<(tert-Butyldiphenylsilyl)oxy>-1'-hydroxyethyl>-4-hydroxy-2-oxo-1-oxacyclopentane

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Technology Process of (4R,5S,1'R)-5-<2'-<(tert-Butyldiphenylsilyl)oxy>-1'-hydroxyethyl>-4-hydroxy-2-oxo-1-oxacyclopentane

There total 1 articles about (4R,5S,1'R)-5-<2'-<(tert-Butyldiphenylsilyl)oxy>-1'-hydroxyethyl>-4-hydroxy-2-oxo-1-oxacyclopentane 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: 96.0%

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

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

Guidance literature:: With chloro-trimethyl-silane; zinc; In dichloromethane; for 0.0333333h; Ambient temperature;
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

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

Guidance literature:: Multi-step reaction with 2 steps

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

2: HMDS, pyridine / 3 h / Ambient temperature

With pyridine; trimethylaluminum; 1,1,1,3,3,3-hexamethyl-disilazane; In 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

: Methyl (4R,5S,6R)-7-<(tert-butyldiphenylsilyl)oxy>-4,5-bis(benzyloxy)-3-deoxy-2-heptuloso-2,6-pyranoside

Guidance literature:: Multi-step reaction with 8 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

4: p-TsOH / 4 h / 50 °C

5: NaH, n-Bu₄NI / tetrahydrofuran / Ambient temperature

6: 1.) molecular sieves 4 Angstroem / 1.) CH₃CN, 10 min, r.t., 2.) 15 min

7: NaBH₄ / methanol / 0.17 h / 0 °C

8: CuO, aq. CuCl₂ / acetonitrile / 0.25 h / Ambient temperature

With pyridine; sodium tetrahydroborate; n-butyllithium; 4 A molecular sieve; trimethylaluminum; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane; copper(II) oxide; copper dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1021/jo00127a047