4-{(E)-2-[(2R,3R,4S,5S,6R)-6-(2,2-Dimethoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-2-methyl-oxazole

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Chemical Name:4-{(E)-2-[(2R,3R,4S,5S,6R)-6-(2,2-Dimethoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-2-methyl-oxazole
CAS No.:552849-99-7
Molecular Formula:C₂₆H₃₇NO₆
Molecular Weight:459.583
Hs Code.:

Synonyms:4-{(E)-2-[(2R,3R,4S,5S,6R)-6-(2,2-Dimethoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-2-methyl-oxazole

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Chemical Property of 4-{(E)-2-[(2R,3R,4S,5S,6R)-6-(2,2-Dimethoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-2-methyl-oxazole

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Technology Process of 4-{(E)-2-[(2R,3R,4S,5S,6R)-6-(2,2-Dimethoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-2-methyl-oxazole

There total 16 articles about 4-{(E)-2-[(2R,3R,4S,5S,6R)-6-(2,2-Dimethoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-2-methyl-oxazole 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: 49.0%

: 552849-98-6
dimethyl ((2-methyloxazol-4-yl)methyl)phosphonate

: 552849-97-5
(2R,3R,4R,5R,6R)-2-(2-dimethoxyethylacetal)-6-(1-oxoethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran

: 552849-99-7
4-{(E)-2-[(2R,3R,4S,5S,6R)-6-(2,2-Dimethoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-2-methyl-oxazole

Guidance literature:: dimethyl ((2-methyloxazol-4-yl)methyl)phosphonate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

(2R,3R,4R,5R,6R)-2-(2-dimethoxyethylacetal)-6-(1-oxoethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran; In tetrahydrofuran; at -78 - 20 ℃; for 5h; Further stages.;
DOI:10.1039/b308305e

Reference yield:

: 201854-68-4
1-[6-allyl-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydropyran-2-yl]-ethane-1,2-diol

: 552849-99-7
4-{(E)-2-[(2R,3R,4S,5S,6R)-6-(2,2-Dimethoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-2-methyl-oxazole

Guidance literature:: Multi-step reaction with 8 steps

1: N-tosylimidazole; NaH / diethyl ether / -78 - 0 °C

2: LiAlH₄ / diethyl ether

3: 2,6-lutidine / CH₂Cl₂ / -78 - 20 °C

4: OsO₄; N-methylmorpholine N-oxide / acetone; H₂O

5: NaIO₄ on silica / CH₂Cl₂

6: camphorsulfonic acid / CH₂Cl₂

7: Dess-Martin periodinane; 2,6-lutidine / CH₂Cl₂

8: 89 percent Turnov_. / lithium diisopropylamide / 0.5 h / -78 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; sodium hydride; Dess-Martin periodane; 4-methylmorpholine N-oxide; N-tosylimidazole; lithium diisopropyl amide; In diethyl ether; dichloromethane; water; acetone; 7: Dess-Martin oxidation / 8: Wadsworth-Emmons olefination;
DOI:10.1002/anie.200390321

Reference yield:

: 1-[(2R,3R,4S,5S,6R)-6-Allyl-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone

: 552849-99-7
4-{(E)-2-[(2R,3R,4S,5S,6R)-6-(2,2-Dimethoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-2-methyl-oxazole

Guidance literature:: Multi-step reaction with 7 steps

1: LiAlH₄ / diethyl ether

2: 2,6-lutidine / CH₂Cl₂ / -78 - 20 °C

3: OsO₄; N-methylmorpholine N-oxide / acetone; H₂O

4: NaIO₄ on silica / CH₂Cl₂

5: camphorsulfonic acid / CH₂Cl₂

6: Dess-Martin periodinane; 2,6-lutidine / CH₂Cl₂

7: 89 percent Turnov_. / lithium diisopropylamide / 0.5 h / -78 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; Dess-Martin periodane; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In diethyl ether; dichloromethane; water; acetone; 6: Dess-Martin oxidation / 7: Wadsworth-Emmons olefination;
DOI:10.1002/anie.200390321