(2S,3R,4S,6R)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptane-1,3-diol

Base Information

Chemical Name:(2S,3R,4S,6R)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptane-1,3-diol
CAS No.:474410-97-4
Molecular Formula:C₁₉H₃₁NO₈
Molecular Weight:401.457
Hs Code.:

Synonyms:(2S,3R,4S,6R)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptane-1,3-diol

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Chemical Property of (2S,3R,4S,6R)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptane-1,3-diol

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Technology Process of (2S,3R,4S,6R)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptane-1,3-diol

There total 11 articles about (2S,3R,4S,6R)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptane-1,3-diol 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: 80.0%

: 474411-11-5
(2S,3R,4S,6R)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptane-1,3-diol-1,3-bis-(tert-butyl-dimethyl-silyl) ether

: 474410-97-4
(2S,3R,4S,6R)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptane-1,3-diol

: 474411-20-6
(2S,3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptan-1-ol

Guidance literature:: With camphor-10-sulfonic acid; In methanol; dichloromethane; at 0 ℃; for 2.5h;
DOI:10.1021/jo034870l

Reference yield: 78.0%

: 474411-10-4
(3R,4S,6R)-2,6-dimethyl-3-hydroxy-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-hept-1-ene

: 474411-22-8
(2R,3R,4S,6R)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptane-1,3-diol

: 474410-97-4
(2S,3R,4S,6R)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptane-1,3-diol

Guidance literature:: (3R,4S,6R)-2,6-dimethyl-3-hydroxy-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-hept-1-ene; With borane-THF; In tetrahydrofuran; at -5 ℃; for 2.25h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 2h;
DOI:10.1021/jo034870l

Reference yield:

: 326606-16-0
(3S,5S,6S)-3-[(1S,3R)-1-hydroxy-3-methyl-4-(5-nitro-2,3,6-trimethoxy-phenyl)-butyl]-5,6-bis-(4-methoxy-phenyl)-[1,4]dioxan-2-one

: 474410-97-4
(2S,3R,4S,6R)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptane-1,3-diol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 91 percent / proton sponge / CH₂Cl₂ / 8 h / 20 °C

2.1: 89 percent / methanol; tetrahydrofuran / 2.5 h / 0 °C

3.1: 95 percent / ceric ammonium nitrate (CAN); H₂O / acetonitrile / 0.5 h / 0 °C

4.1: 99 percent / imidazole / dimethylformamide / 18 h / 20 °C

5.1: 90 percent / DIBAL-H / CH₂Cl₂; toluene / 3 h / -78 °C

6.1: 80 percent / CH₂Cl₂ / 2.5 h / -78 °C

7.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

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

8.2: 98 percent / diethyl ether / 2 h / 20 °C

9.1: 99 percent / aq. HF / acetonitrile / 3 h / 20 °C

10.1: BH₃*THF / tetrahydrofuran / 2.25 h / -5 °C

10.2: 78 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran; methanol / 2 h / 0 - 20 °C

With 1H-imidazole; borane-THF; Proton Sponge; ammonium cerium(IV) nitrate; hydrogen fluoride; water; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 8.2: Wittig reaction;
DOI:10.1021/jo034870l