4-{(2R,4R,6R)-6-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-4-bromo-tetrahydro-pyran-2-yl}-2-chloromethyl-oxazole

Base Information

Chemical Name:4-{(2R,4R,6R)-6-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-4-bromo-tetrahydro-pyran-2-yl}-2-chloromethyl-oxazole
CAS No.:862814-48-0
Molecular Formula:C₂₅H₃₁BrClNO₄
Molecular Weight:524.882
Hs Code.:

Synonyms:4-{(2R,4R,6R)-6-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-4-bromo-tetrahydro-pyran-2-yl}-2-chloromethyl-oxazole

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Chemical Property of 4-{(2R,4R,6R)-6-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-4-bromo-tetrahydro-pyran-2-yl}-2-chloromethyl-oxazole

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Technology Process of 4-{(2R,4R,6R)-6-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-4-bromo-tetrahydro-pyran-2-yl}-2-chloromethyl-oxazole

There total 9 articles about 4-{(2R,4R,6R)-6-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-4-bromo-tetrahydro-pyran-2-yl}-2-chloromethyl-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: 70.0%

: 862814-46-8
Acetic acid {(S)-1-[(2R,6R)-6-(2-benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-but-3-enyloxy}-(2-chloromethyl-oxazol-4-yl)-methyl ester

: 862814-48-0
4-{(2R,4R,6R)-6-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-4-bromo-tetrahydro-pyran-2-yl}-2-chloromethyl-oxazole

Guidance literature:: With trimethylsilyl bromide; In dichloromethane; at 0 ℃; for 3h;
DOI:10.1021/ol051039h

Reference yield:

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

: 862814-48-0
4-{(2R,4R,6R)-6-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-4-bromo-tetrahydro-pyran-2-yl}-2-chloromethyl-oxazole

Guidance literature:: Multi-step reaction with 8 steps

1.1: 1.3 g / pyridine; DMAP / CH₂Cl₂ / 2.5 h / 0 °C

2.1: 79 percent / TMSOTf / CH₂Cl₂ / 2 h / -78 °C

3.1: 91 percent / DIBAL-H / CH₂Cl₂; toluene / 0.25 h / -78 °C

4.1: diethyl ether / 0.58 h / -100 - -78 °C

4.2: 79 percent / NaOH; H₂O₂ / diethyl ether; methanol; H₂O / 1.5 h / 0 °C

5.1: 98 percent / dicyclohexylcarbodiimide; N,N-dimethylaminopyridine / CH₂Cl₂ / 12 h / 25 °C

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

7.1: 43.6 mg / DMAP; pyridine / CH₂Cl₂; hexane / -94 - -20 °C

8.1: 70 percent / TMSBr / CH₂Cl₂ / 3 h / 0 °C

With pyridine; dmap; trimethylsilyl bromide; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; In diethyl ether; hexane; dichloromethane; toluene; 4.1: Brown allylation / 8.1: Prins reaction;
DOI:10.1021/ol051039h

Reference yield:

: 862814-40-2
[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-yl]-acetaldehyde

: 862814-48-0
4-{(2R,4R,6R)-6-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-4-bromo-tetrahydro-pyran-2-yl}-2-chloromethyl-oxazole

Guidance literature:: Multi-step reaction with 5 steps

1.1: diethyl ether / 0.58 h / -100 - -78 °C

1.2: 79 percent / NaOH; H₂O₂ / diethyl ether; methanol; H₂O / 1.5 h / 0 °C

2.1: 98 percent / dicyclohexylcarbodiimide; N,N-dimethylaminopyridine / CH₂Cl₂ / 12 h / 25 °C

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

4.1: 43.6 mg / DMAP; pyridine / CH₂Cl₂; hexane / -94 - -20 °C

5.1: 70 percent / TMSBr / CH₂Cl₂ / 3 h / 0 °C

With pyridine; dmap; trimethylsilyl bromide; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; In diethyl ether; hexane; dichloromethane; 1.1: Brown allylation / 5.1: Prins reaction;
DOI:10.1021/ol051039h