(-)-(1R,3S,4S,6S)-6-endo-benzyloxy-2-oxo-7-oxabicyclo<2.2.1>hept-3-exo-yl acetate

Base Information

Chemical Name:(-)-(1R,3S,4S,6S)-6-endo-benzyloxy-2-oxo-7-oxabicyclo<2.2.1>hept-3-exo-yl acetate
CAS No.:128503-19-5
Molecular Formula:C₁₅H₁₆O₅
Molecular Weight:276.289
Hs Code.:

Synonyms:(-)-(1R,3S,4S,6S)-6-endo-benzyloxy-2-oxo-7-oxabicyclo<2.2.1>hept-3-exo-yl acetate

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Chemical Property of (-)-(1R,3S,4S,6S)-6-endo-benzyloxy-2-oxo-7-oxabicyclo<2.2.1>hept-3-exo-yl acetate

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Technology Process of (-)-(1R,3S,4S,6S)-6-endo-benzyloxy-2-oxo-7-oxabicyclo<2.2.1>hept-3-exo-yl acetate

There total 9 articles about (-)-(1R,3S,4S,6S)-6-endo-benzyloxy-2-oxo-7-oxabicyclo<2.2.1>hept-3-exo-yl acetate 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: 94.0%

: 108-24-7
acetic anhydride

: 128503-18-4
(-)-(1R,3S,4S,6S)-6-endo-benzyloxy-3-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one

: 128503-19-5
(-)-(1R,3S,4S,6S)-6-endo-benzyloxy-2-oxo-7-oxabicyclo<2.2.1>hept-3-exo-yl acetate

Guidance literature:: With pyridine; dmap; at 20 ℃; for 15h;
DOI:10.1016/S0040-4039(00)70712-X

Reference yield:

: 128503-15-1
(+)-(1R,4S,5S,6S)-5-exo-benzeneselenyl-6-endo-bromo-7-oxabicyclo<2.2.1>heptan-2-one

: 128503-19-5
(-)-(1R,3S,4S,6S)-6-endo-benzyloxy-2-oxo-7-oxabicyclo<2.2.1>hept-3-exo-yl acetate

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / mCPBA / CH₂Cl₂ / a) -78 deg C, b) 20 deg C, 5 h

2: 95 percent / NaBH₄ / methanol / 1 h / 0 °C

3: 1) NaH, 2) tetrabutylammonium iodide / 1) THF, 0 deg C, 2) 20 deg C, 4 h

4: 99 percent / NaHCO₃, OsO₄, 30percent H₂O₂ / tetrahydrofuran; CCl₄ / 2 h / 0 °C

5: 94 percent / DMAP, pyridine / 12 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; osmium(VIII) oxide; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane;
DOI:10.1016/S0040-4020(01)88356-3

Reference yield:

: 128530-69-8
(-)-(1R,4S,6S)-6-endo-benzyloxy-2-bromo-7-oxabicyclo<2.2.1>hept-2-ene

: 128503-19-5
(-)-(1R,3S,4S,6S)-6-endo-benzyloxy-2-oxo-7-oxabicyclo<2.2.1>hept-3-exo-yl acetate

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / NaHCO₃, OsO₄, 30percent H₂O₂ / tetrahydrofuran; CCl₄ / 2 h / 0 °C

2: 94 percent / DMAP, pyridine / 12 h / 20 °C

With pyridine; dmap; osmium(VIII) oxide; dihydrogen peroxide; sodium hydrogencarbonate; In tetrahydrofuran; tetrachloromethane;
DOI:10.1016/S0040-4020(01)88356-3