(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
• Mol file: 172293-71-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

(3R,4R,5R)-tert-butyl <6-(tert-butyldiphenylsilyloxy)-4,5-epoxy-3-hydroxy>hexanoate (153321-80-3) → (4R,5S,1'R)-5-<2'-<(tert-Butyldiphenylsilyl)oxy>-1'-hydroxyethyl>-4-hydroxy-2-oxo-1-oxacyclopentane (172293-71-9)

Guidance literature:

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

DOI:10.1021/jo00127a047

Reference yield:

(4R,5S,1'R)-5-<2'-<(tert-Butyldiphenylsilyl)oxy>-1'-hydroxyethyl>-4-hydroxy-2-oxo-1-oxacyclopentane (172293-71-9) → (3R,4S,5R)-6-<(tert-Butyldiphenylsilyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-N-methoxy-N-methylhexanamide (172293-73-1)

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:

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

upstream raw materials:

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

Downstream raw materials:

(3R,4S,5R)-6-(tert-Butyl-diphenyl-silanyloxy)-3,4,5-trihydroxy-hexanoic acid methoxy-methyl-amide

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

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