(-)-(2R,3S,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-tetrahydropyran-4-one

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Chemical Name:(-)-(2R,3S,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-tetrahydropyran-4-one
CAS No.:875545-13-4
Molecular Formula:C₁₉H₂₄O₇
Molecular Weight:364.395
Hs Code.:

Synonyms:(-)-(2R,3S,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-tetrahydropyran-4-one

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Chemical Property of (-)-(2R,3S,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-tetrahydropyran-4-one

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Technology Process of (-)-(2R,3S,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-tetrahydropyran-4-one

There total 3 articles about (-)-(2R,3S,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-tetrahydropyran-4-one 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: 82.0%

: 875545-12-3
Acetic acid (2R,3R,4R,6R)-6-acetoxymethyl-4-hydroxy-3-((S)-1-phenyl-ethoxy)-tetrahydro-pyran-2-ylmethyl ester

: 875545-13-4
(-)-(2R,3S,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-tetrahydropyran-4-one

Guidance literature:: Acetic acid (2R,3R,4R,6R)-6-acetoxymethyl-4-hydroxy-3-((S)-1-phenyl-ethoxy)-tetrahydro-pyran-2-ylmethyl ester; With 4 A molecular sieve; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 0.166667h;

With tetrapropylammonium perruthennate; In dichloromethane;
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

: 875545-13-4
(-)-(2R,3S,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-tetrahydropyran-4-one

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

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

: 875545-13-4
(-)-(2R,3S,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-tetrahydropyran-4-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

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

2.2: 82 percent / tetra-n-propylammonium perruthenate / CH₂Cl₂

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