(E)-(2S,5S,6R)-2-Benzyloxy-6-(2,5-dimethoxy-3-nitro-phenyl)-6-methoxy-5-methyl-hex-3-enoic acid methyl ester

Base Information

Chemical Name:(E)-(2S,5S,6R)-2-Benzyloxy-6-(2,5-dimethoxy-3-nitro-phenyl)-6-methoxy-5-methyl-hex-3-enoic acid methyl ester
CAS No.:170901-51-6
Molecular Formula:C₂₄H₂₉NO₈
Molecular Weight:459.496
Hs Code.:

Synonyms:(E)-(2S,5S,6R)-2-Benzyloxy-6-(2,5-dimethoxy-3-nitro-phenyl)-6-methoxy-5-methyl-hex-3-enoic acid methyl ester

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Chemical Property of (E)-(2S,5S,6R)-2-Benzyloxy-6-(2,5-dimethoxy-3-nitro-phenyl)-6-methoxy-5-methyl-hex-3-enoic acid methyl ester

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Technology Process of (E)-(2S,5S,6R)-2-Benzyloxy-6-(2,5-dimethoxy-3-nitro-phenyl)-6-methoxy-5-methyl-hex-3-enoic acid methyl ester

There total 1 articles about (E)-(2S,5S,6R)-2-Benzyloxy-6-(2,5-dimethoxy-3-nitro-phenyl)-6-methoxy-5-methyl-hex-3-enoic acid 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: 92.0%

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

: (2R,3R,E)-methyl 2-(benzyloxy)-3-(dimethyl(phenyl)silyl)hex-4-enoate

: 170901-51-6
(E)-(2S,5S,6R)-2-Benzyloxy-6-(2,5-dimethoxy-3-nitro-phenyl)-6-methoxy-5-methyl-hex-3-enoic acid methyl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃;
DOI:10.1021/ja00147a027

Reference yield: 85.0%

: 170901-51-6
(E)-(2S,5S,6R)-2-Benzyloxy-6-(2,5-dimethoxy-3-nitro-phenyl)-6-methoxy-5-methyl-hex-3-enoic acid methyl ester

: 170901-52-7
(2R,3S,5S,6R)-2-Benzyloxy-6-(2,5-dimethoxy-3-nitro-phenyl)-6-methoxy-5-methyl-hexane-1,3-diol

Guidance literature:: With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃; for 16h;
DOI:10.1021/ja00147a027

Reference yield:

: 170901-51-6
(E)-(2S,5S,6R)-2-Benzyloxy-6-(2,5-dimethoxy-3-nitro-phenyl)-6-methoxy-5-methyl-hex-3-enoic acid methyl ester

: 170707-54-7
(2R,3R,4S,6S,7R)-7-(2,5-dimethoxy-3-nitrophenyl)-3,4,7-trimethoxy-2,6-dimethylheptanal

Guidance literature:: Multi-step reaction with 16 steps

1: 1.) BH₃*SMe₂, 2.) 5M aq. NaOH, 30percent H₂O₂ / 1.) THF, from 0 deg C to RT, 18 h, 2.) THF, from 0 deg C to RT, 120 min

2: imidazole / diethyl ether; dimethylformamide / 0 °C

3: 2,6-di-tert-butylpyridine / CH₂Cl₂ / Ambient temperature

4: n-Bu₄NF / tetrahydrofuran

5: 95 percent / BCl₃*SMe₂ / CH₂Cl₂ / -78 - 0 °C

6: 99 percent / imidazole / dimethylformamide / 0 °C

7: 90 percent / HF*Pyr / tetrahydrofuran

8: 1.) (COCl)2, DMSO, 2.) Et₃N

9: 91 percent / CH₂Cl₂ / -78 °C

10: 1.) (COCl)2, DMSO, 2.) Et₃N

11: 90 percent / NaNH₂ / diethyl ether / 0 °C

12: 100 percent / 48percent aq. HF / acetonitrile / 1 h / Ambient temperature

13: 1.) BH₃, 2.) 3 M aq. NaOH, 30percent H₂O₂ / 1.) THF, -5 deg C, 45 min, 2.) THF, from 0 deg C to RT, 120 min

14: 98 percent / Et₃N / tetrahydrofuran / 0.25 h / -78 °C

15: 1.) proton sponge / 1.) CH₂Cl₂, RT, 2 h, 2.) 1 N aq. NaHSO₄

16: 1.) (COCl)2, DMSO, 2.) Et₃N

With 1H-imidazole; sodium hydroxide; 2,6-di-tert-butyl-pyridine; oxalyl dichloride; Proton Sponge; dimethylsulfide borane complex; boron trichloride - methyl sulfide complex; hydrogen fluoride; borane; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridine hydrogenfluoride; sodium amide; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja974318b