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

Base Information

Chemical Name:4-{(2R,4S,6R)-6-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-2-chloromethyl-oxazole
CAS No.:862814-60-6
Molecular Formula:C₃₄H₅₂ClNO₅Si
Molecular Weight:618.329
Hs Code.:

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

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

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

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

There total 19 articles about 4-{(2R,4S,6R)-6-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-4-triisopropylsilanyloxy-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: 100.0%

: 862814-52-6
(2S,4S,6R)-2-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-6-(2-chloromethyl-oxazol-4-yl)-tetrahydro-pyran-4-ol

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 862814-60-6
4-{(2R,4S,6R)-6-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-2-chloromethyl-oxazole

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.333333h;
DOI:10.1021/ol051039h

Reference yield:

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

: 862814-60-6
4-{(2R,4S,6R)-6-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-2-chloromethyl-oxazole

Guidance literature:: Multi-step reaction with 10 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: CH₂Cl₂ / 0.25 h / 0 °C

9.1: 0.361 g / K₂CO₃ / methanol / 0.17 h / 0 °C

10.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; potassium carbonate; dicyclohexyl-carbodiimide; In methanol; diethyl ether; hexane; dichloromethane; toluene; 4.1: Brown allylation / 8.1: Prins reaction;
DOI:10.1021/ol051039h

Reference yield:

: 862814-28-6
[6-(2-benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-yl]-thioacetic acid S-tert-butyl ester

: 862814-60-6
4-{(2R,4S,6R)-6-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-2-chloromethyl-oxazole

Guidance literature:: Multi-step reaction with 8 steps

1.1: 91 percent / DIBAL-H / CH₂Cl₂; toluene / 0.25 h / -78 °C

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

2.2: 79 percent / NaOH; H₂O₂ / diethyl ether; methanol; H₂O / 1.5 h / 0 °C

3.1: 98 percent / dicyclohexylcarbodiimide; N,N-dimethylaminopyridine / CH₂Cl₂ / 12 h / 25 °C

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

5.1: 43.6 mg / DMAP; pyridine / CH₂Cl₂; hexane / -94 - -20 °C

6.1: CH₂Cl₂ / 0.25 h / 0 °C

7.1: 0.361 g / K₂CO₃ / methanol / 0.17 h / 0 °C

8.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; diisobutylaluminium hydride; potassium carbonate; dicyclohexyl-carbodiimide; In methanol; diethyl ether; hexane; dichloromethane; toluene; 2.1: Brown allylation / 6.1: Prins reaction;
DOI:10.1021/ol051039h