2-Chloromethyl-oxazole-4-carboxylic acid (S)-1-[(2R,6R)-6-(2-benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-but-3-enyl ester

Base Information

Chemical Name:2-Chloromethyl-oxazole-4-carboxylic acid (S)-1-[(2R,6R)-6-(2-benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-but-3-enyl ester
CAS No.:862814-64-0
Molecular Formula:C₂₅H₃₀ClNO₅
Molecular Weight:459.97
Hs Code.:

Synonyms:2-Chloromethyl-oxazole-4-carboxylic acid (S)-1-[(2R,6R)-6-(2-benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-but-3-enyl ester

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Chemical Property of 2-Chloromethyl-oxazole-4-carboxylic acid (S)-1-[(2R,6R)-6-(2-benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-but-3-enyl ester

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Technology Process of 2-Chloromethyl-oxazole-4-carboxylic acid (S)-1-[(2R,6R)-6-(2-benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-but-3-enyl ester

There total 7 articles about 2-Chloromethyl-oxazole-4-carboxylic acid (S)-1-[(2R,6R)-6-(2-benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-but-3-enyl ester 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: 98.0%

: 862814-42-4
(S)-1-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-yl]-pent-4-en-2-ol

: 208465-62-7
2-(chloromethyl)oxazole-4-carboxylic acid

: 862814-64-0
2-Chloromethyl-oxazole-4-carboxylic acid (S)-1-[(2R,6R)-6-(2-benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-but-3-enyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 25 ℃; for 12h;
DOI:10.1021/ol051039h

Reference yield:

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

: 862814-64-0
2-Chloromethyl-oxazole-4-carboxylic acid (S)-1-[(2R,6R)-6-(2-benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-but-3-enyl ester

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

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

: 862814-64-0
2-Chloromethyl-oxazole-4-carboxylic acid (S)-1-[(2R,6R)-6-(2-benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-but-3-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1.70 g / IBX / dimethylsulfoxide; acetone / 3.5 h / 25 °C

2.1: 1.3 g / pyridine; DMAP / CH₂Cl₂ / 2.5 h / 0 °C

3.1: 79 percent / TMSOTf / CH₂Cl₂ / 2 h / -78 °C

4.1: 91 percent / DIBAL-H / CH₂Cl₂; toluene / 0.25 h / -78 °C

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

5.2: 79 percent / NaOH; H₂O₂ / diethyl ether; methanol; H₂O / 1.5 h / 0 °C

6.1: 98 percent / dicyclohexylcarbodiimide; N,N-dimethylaminopyridine / CH₂Cl₂ / 12 h / 25 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In diethyl ether; dichloromethane; dimethyl sulfoxide; acetone; toluene; 5.1: Brown allylation;
DOI:10.1021/ol051039h