(3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-hept-1-ene

Base Information

Chemical Name:(3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-hept-1-ene
CAS No.:474410-96-3
Molecular Formula:C₂₅H₄₃NO₇Si
Molecular Weight:497.704
Hs Code.:

Synonyms:(3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-hept-1-ene

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Chemical Property of (3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-hept-1-ene

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Technology Process of (3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-hept-1-ene

There total 6 articles about (3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-hept-1-ene 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%

: 19493-09-5
Methylenetriphenylphosphorane

: 474411-09-1
(3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptan-2-one

: 474410-96-3
(3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-hept-1-ene

Guidance literature:: In diethyl ether; at -78 - 20 ℃; for 2h;
DOI:10.1021/ol0267432

Reference yield:

: 326606-26-2
(3S,5S,6S)-3-[(1S,3R)-1-methoxy-3-methyl-4-(5-nitro-2,3,6-trimethoxy-phenyl)-butyl]-5,6-bis-(4-methoxy-phenyl)-[1,4]dioxan-2-one

: 474410-96-3
(3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-hept-1-ene

Guidance literature:: Multi-step reaction with 7 steps

1.1: 89 percent / methanol; tetrahydrofuran / 2.5 h / 0 °C

2.1: 95 percent / ceric ammonium nitrate (CAN); H₂O / acetonitrile / 0.5 h / 0 °C

3.1: 99 percent / imidazole / dimethylformamide / 18 h / 20 °C

4.1: 90 percent / DIBAL-H / CH₂Cl₂; toluene / 3 h / -78 °C

5.1: 80 percent / CH₂Cl₂ / 2.5 h / -78 °C

6.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

7.1: NaHMDS / diethyl ether / 1 h / 0 - 20 °C

7.2: 98 percent / diethyl ether / 2 h / 20 °C

With 1H-imidazole; ammonium cerium(IV) nitrate; water; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 7.2: Wittig reaction;
DOI:10.1021/jo034870l

Reference yield:

: 474411-08-0
(2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-5-methyl-6-(5-nitro-2,3,6-trimethoxy-phenyl)-hexanal

: 474410-96-3
(3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-hept-1-ene

Guidance literature:: Multi-step reaction with 3 steps

1.1: 80 percent / CH₂Cl₂ / 2.5 h / -78 °C

2.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

3.1: NaHMDS / diethyl ether / 1 h / 0 - 20 °C

3.2: 98 percent / diethyl ether / 2 h / 20 °C

With sodium hexamethyldisilazane; Dess-Martin periodane; In diethyl ether; dichloromethane; 3.2: Wittig reaction;
DOI:10.1021/jo034870l