(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

Base Information

Chemical Name:(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
CAS No.:862814-52-6
Molecular Formula:C₂₅H₃₂ClNO₅
Molecular Weight:461.986
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 18 articles about (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 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: 82.0%

: 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

: 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

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.166667h;
DOI:10.1021/ol051039h

Reference yield:

: Trifluoro-acetic acid (2R,6R)-2-[(2R,6R)-6-(2-benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-6-(2-chloromethyl-oxazol-4-yl)-tetrahydro-pyran-4-yl ester

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

: 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

Guidance literature:: With potassium carbonate; In methanol; at 0 ℃; for 0.166667h;
DOI:10.1021/ol051039h

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 9 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

With pyridine; 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