[(2R,3S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxymethyl-3-((S)-1-phenyl-ethoxy)-tetrahydro-pyran-2-yl]-methanol

Base Information

Chemical Name:[(2R,3S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxymethyl-3-((S)-1-phenyl-ethoxy)-tetrahydro-pyran-2-yl]-methanol
CAS No.:875545-10-1
Molecular Formula:C₂₁H₃₆O₅Si
Molecular Weight:396.599
Hs Code.:

Synonyms:[(2R,3S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxymethyl-3-((S)-1-phenyl-ethoxy)-tetrahydro-pyran-2-yl]-methanol

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Chemical Property of [(2R,3S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxymethyl-3-((S)-1-phenyl-ethoxy)-tetrahydro-pyran-2-yl]-methanol

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Technology Process of [(2R,3S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxymethyl-3-((S)-1-phenyl-ethoxy)-tetrahydro-pyran-2-yl]-methanol

There total 1 articles about [(2R,3S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxymethyl-3-((S)-1-phenyl-ethoxy)-tetrahydro-pyran-2-yl]-methanol 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: 92.0%

: 875545-09-8
(-)-(1R,2S,3R,5R)-2-((S)-1-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-ene

: 875545-10-1
[(2R,3S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxymethyl-3-((S)-1-phenyl-ethoxy)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: (-)-(1R,2S,3R,5R)-2-((S)-1-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-ene; With ozone; In methanol; dichloromethane; at -78 ℃;

With sodium tetrahydroborate; In methanol; dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/j.tet.2005.08.112

Reference yield: 76.0%

: 875545-10-1
[(2R,3S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxymethyl-3-((S)-1-phenyl-ethoxy)-tetrahydro-pyran-2-yl]-methanol

: 108-24-7
acetic anhydride

: 875545-11-2
(-)-(2R,3S,4R,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-4-(tert-butyldimethylsilanyloxy)-tetrahydropyran

Guidance literature:: With pyridine; at 20 ℃; for 24h;
DOI:10.1016/j.tet.2005.08.112

Reference yield:

: 875545-10-1
[(2R,3S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxymethyl-3-((S)-1-phenyl-ethoxy)-tetrahydro-pyran-2-yl]-methanol

: 875545-16-7
(+)-(2R,3S,6R)-2,6-bis-acetoxymethyl-3-benzoyloxy-tetrahydropyran-4-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 76 percent / pyridine / 24 h / 20 °C

2.1: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

3.1: molecular sieves 4 Angstroem; N-methylmorpholine N-oxide / CH₂Cl₂ / 0.17 h / 20 °C

3.2: 82 percent / tetra-n-propylammonium perruthenate / CH₂Cl₂

4.1: anhydrous FeCl₃ / CH₂Cl₂ / 0 - 20 °C

4.2: 56 percent / CH₂Cl₂ / 0.17 h

With pyridine; 4 A molecular sieve; tetrabutyl ammonium fluoride; iron(III) chloride; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2005.08.112