(E)-(2R,5S,6R)-Methyl 2-acetoxy-6-(2,5-dimethoxy-3-nitrophenyl)-6-methoxy-5-methylhex-3-enoate

Base Information

Chemical Name:(E)-(2R,5S,6R)-Methyl 2-acetoxy-6-(2,5-dimethoxy-3-nitrophenyl)-6-methoxy-5-methylhex-3-enoate
CAS No.:146962-15-4
Molecular Formula:C₁₉H₂₅NO₉
Molecular Weight:411.409
Hs Code.:

Synonyms:(E)-(2R,5S,6R)-Methyl 2-acetoxy-6-(2,5-dimethoxy-3-nitrophenyl)-6-methoxy-5-methylhex-3-enoate

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Chemical Property of (E)-(2R,5S,6R)-Methyl 2-acetoxy-6-(2,5-dimethoxy-3-nitrophenyl)-6-methoxy-5-methylhex-3-enoate

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Technology Process of (E)-(2R,5S,6R)-Methyl 2-acetoxy-6-(2,5-dimethoxy-3-nitrophenyl)-6-methoxy-5-methylhex-3-enoate

There total 3 articles about (E)-(2R,5S,6R)-Methyl 2-acetoxy-6-(2,5-dimethoxy-3-nitrophenyl)-6-methoxy-5-methylhex-3-enoate 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: 90.0%

: 134333-50-9
2,5-dimethoxy-3-nitrobenzaldehyde dimethyl acetal

: 146962-08-5
(2S,3R)-(E)-Methyl 2-acetoxy-3-(dimethylphenylsilyl)-hex-4-enoate

: 146962-15-4
(E)-(2R,5S,6R)-Methyl 2-acetoxy-6-(2,5-dimethoxy-3-nitrophenyl)-6-methoxy-5-methylhex-3-enoate

Guidance literature:: trimethylsilyl trifluoromethanesulfonate; In dichloromethane; a) -78 deg C to -65 deg C, b) -65 deg C;
DOI:10.1021/jo00057a008

Reference yield:

: 146962-07-4
(2S,3R)-(E)-Methyl 3-(dimethylphenylsilyl)-2-hydroxy-hex-4-enoate

: 146962-15-4
(E)-(2R,5S,6R)-Methyl 2-acetoxy-6-(2,5-dimethoxy-3-nitrophenyl)-6-methoxy-5-methylhex-3-enoate

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / Et₃N, DMAP / CH₂Cl₂ / a) 0 deg C to r.t., 3 h, b) r.t., 3 h

2: 90 percent / trimethylsilyl trifluoromethanesulfonate (TMSOTf) / CH₂Cl₂ / a) -78 deg C to -65 deg C, b) -65 deg C

With dmap; triethylamine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;
DOI:10.1021/jo00057a008

Reference yield:

: 222300-44-9
(4E)-Methyl 3-(dimethylphenylsilyl)-4-hexenoate

: 146962-15-4
(E)-(2R,5S,6R)-Methyl 2-acetoxy-6-(2,5-dimethoxy-3-nitrophenyl)-6-methoxy-5-methylhex-3-enoate

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) KN(TMS)2, trans-3-phenyl-2-(phenylsulfonyl)oxaziridine, 2.) camphorsulfonic acid / 1.) THF, toluene, -78 deg C, 2.5 h, 2.) -78 deg C to r.t., 16 h

2: 94 percent / Et₃N, DMAP / CH₂Cl₂ / a) 0 deg C to r.t., 3 h, b) r.t., 3 h

3: 90 percent / trimethylsilyl trifluoromethanesulfonate (TMSOTf) / CH₂Cl₂ / a) -78 deg C to -65 deg C, b) -65 deg C

With dmap; camphor-10-sulfonic acid; potassium hexamethylsilazane; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;
DOI:10.1021/jo00057a008