(2R,6R)-2-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-6-(2-chloromethyl-oxazol-4-yl)-tetrahydro-pyran-4-one

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Chemical Name:(2R,6R)-2-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-6-(2-chloromethyl-oxazol-4-yl)-tetrahydro-pyran-4-one
CAS No.:862814-36-6
Molecular Formula:C₂₅H₃₀ClNO₅
Molecular Weight:459.97
Hs Code.:

Synonyms:(2R,6R)-2-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-6-(2-chloromethyl-oxazol-4-yl)-tetrahydro-pyran-4-one

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Chemical Property of (2R,6R)-2-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-6-(2-chloromethyl-oxazol-4-yl)-tetrahydro-pyran-4-one

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Technology Process of (2R,6R)-2-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-6-(2-chloromethyl-oxazol-4-yl)-tetrahydro-pyran-4-one

There total 12 articles about (2R,6R)-2-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-6-(2-chloromethyl-oxazol-4-yl)-tetrahydro-pyran-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:

: 862814-67-3
(R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ol

: 862814-36-6
(2R,6R)-2-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-6-(2-chloromethyl-oxazol-4-yl)-tetrahydro-pyran-4-one

Guidance literature:: Multi-step reaction with 8 steps

1: 1.3 g / pyridine; DMAP / CH₂Cl₂ / 2.5 h / 0 °C

2: 79 percent / TMSOTf / CH₂Cl₂ / 2 h / -78 °C

3: 99 percent / KOH / H₂O; methanol / 0.75 h / 25 °C

4: 92 percent / DCC; DMAP / CH₂Cl₂ / 12 h / 25 °C

5: DIBAL-H / CH₂Cl₂; hexane / 1.5 h / -94 °C

6: 1.03 g / DMAP; pyridine / CH₂Cl₂; hexane / -94 - -20 °C

7: TMSOTf / CH₂Cl₂ / 0.08 h / 0 °C

8: 132 mg / Dess-Martin periodinane / CH₂Cl₂ / 0.17 h / 25 °C

With pyridine; dmap; potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; dicyclohexyl-carbodiimide; In methanol; hexane; dichloromethane; water; 7: Prins reaction / 8: Dess-Martin oxidation;
DOI:10.1021/ol051039h

Reference yield:

: 862814-54-8
(R)-7-Benzyloxy-3-methylene-heptane-1,5-diol

: 862814-36-6
(2R,6R)-2-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-6-(2-chloromethyl-oxazol-4-yl)-tetrahydro-pyran-4-one

Guidance literature:: Multi-step reaction with 9 steps

1: 1.70 g / IBX / dimethylsulfoxide; acetone / 3.5 h / 25 °C

2: 1.3 g / pyridine; DMAP / CH₂Cl₂ / 2.5 h / 0 °C

3: 79 percent / TMSOTf / CH₂Cl₂ / 2 h / -78 °C

4: 99 percent / KOH / H₂O; methanol / 0.75 h / 25 °C

5: 92 percent / DCC; DMAP / CH₂Cl₂ / 12 h / 25 °C

6: DIBAL-H / CH₂Cl₂; hexane / 1.5 h / -94 °C

7: 1.03 g / DMAP; pyridine / CH₂Cl₂; hexane / -94 - -20 °C

8: TMSOTf / CH₂Cl₂ / 0.08 h / 0 °C

9: 132 mg / Dess-Martin periodinane / CH₂Cl₂ / 0.17 h / 25 °C

With pyridine; dmap; potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; dicyclohexyl-carbodiimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In methanol; hexane; dichloromethane; water; dimethyl sulfoxide; acetone; 8: Prins reaction / 9: Dess-Martin oxidation;
DOI:10.1021/ol051039h

Reference yield:

: 862814-25-3
Acetic acid (R)-6-(2-benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-yl ester

: 862814-36-6
(2R,6R)-2-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-6-(2-chloromethyl-oxazol-4-yl)-tetrahydro-pyran-4-one

Guidance literature:: Multi-step reaction with 7 steps

1: 79 percent / TMSOTf / CH₂Cl₂ / 2 h / -78 °C

2: 99 percent / KOH / H₂O; methanol / 0.75 h / 25 °C

3: 92 percent / DCC; DMAP / CH₂Cl₂ / 12 h / 25 °C

4: DIBAL-H / CH₂Cl₂; hexane / 1.5 h / -94 °C

5: 1.03 g / DMAP; pyridine / CH₂Cl₂; hexane / -94 - -20 °C

6: TMSOTf / CH₂Cl₂ / 0.08 h / 0 °C

7: 132 mg / Dess-Martin periodinane / CH₂Cl₂ / 0.17 h / 25 °C

With pyridine; dmap; potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; dicyclohexyl-carbodiimide; In methanol; hexane; dichloromethane; water; 6: Prins reaction / 7: Dess-Martin oxidation;
DOI:10.1021/ol051039h