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

Base Information

Chemical Name: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
CAS No.:862814-46-8
Molecular Formula:C₂₇H₃₄ClNO₆
Molecular Weight:504.023
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 8 articles about 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 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:

: {(S)-1-[(2R,6R)-6-(2-Benzyloxy-ethyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-but-3-enyloxy}-(2-chloromethyl-oxazol-4-yl)-methanol

: 108-24-7
acetic anhydride

: 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

Guidance literature:: With pyridine; dmap; In hexane; dichloromethane; at -94 - -20 ℃;
DOI:10.1021/ol051039h

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 7 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

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

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 4 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

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