3-[(5R)-5-(tert-butyldimethylsilanoxy)-(4S)-4-methoxy-(2R)-2,(6S)-6-dimethyl-oct-7-enyl]-2,4,5-trimethoxyphenylamine

Base Information

Chemical Name:3-[(5R)-5-(tert-butyldimethylsilanoxy)-(4S)-4-methoxy-(2R)-2,(6S)-6-dimethyl-oct-7-enyl]-2,4,5-trimethoxyphenylamine
CAS No.:625450-84-2
Molecular Formula:C₂₆H₄₇NO₅Si
Molecular Weight:481.748
Hs Code.:

Synonyms:3-[(5R)-5-(tert-butyldimethylsilanoxy)-(4S)-4-methoxy-(2R)-2,(6S)-6-dimethyl-oct-7-enyl]-2,4,5-trimethoxyphenylamine

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Chemical Property of 3-[(5R)-5-(tert-butyldimethylsilanoxy)-(4S)-4-methoxy-(2R)-2,(6S)-6-dimethyl-oct-7-enyl]-2,4,5-trimethoxyphenylamine

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Technology Process of 3-[(5R)-5-(tert-butyldimethylsilanoxy)-(4S)-4-methoxy-(2R)-2,(6S)-6-dimethyl-oct-7-enyl]-2,4,5-trimethoxyphenylamine

There total 15 articles about 3-[(5R)-5-(tert-butyldimethylsilanoxy)-(4S)-4-methoxy-(2R)-2,(6S)-6-dimethyl-oct-7-enyl]-2,4,5-trimethoxyphenylamine 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: 99.0%

: 625450-94-4
(3S,4R,5S,7R)-4-(tert-butyldimethylsilanoxy)-3,7-dimethyl-5-methoxy-8-(5-nitro-2,3,6-trimethoxyphenyl)octene

: 625450-84-2
3-[(5R)-5-(tert-butyldimethylsilanoxy)-(4S)-4-methoxy-(2R)-2,(6S)-6-dimethyl-oct-7-enyl]-2,4,5-trimethoxyphenylamine

Guidance literature:: With sodium tetrahydroborate; sulfur; In tetrahydrofuran; for 1.5h; Heating;
DOI:10.1021/jo034870l

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

: 625450-84-2
3-[(5R)-5-(tert-butyldimethylsilanoxy)-(4S)-4-methoxy-(2R)-2,(6S)-6-dimethyl-oct-7-enyl]-2,4,5-trimethoxyphenylamine

Guidance literature:: Multi-step reaction with 14 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

8.1: 99 percent / aq. HF / acetonitrile / 3 h / 20 °C

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

9.2: 78 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran; methanol / 2 h / 0 - 20 °C

10.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

11.1: 80 percent / CSA / methanol; CH₂Cl₂ / 2.5 h / 0 °C

12.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 °C

13.1: NaHMDS / diethyl ether / 0 - 20 °C

13.2: 96 mg / diethyl ether / -78 - 20 °C

14.1: 99 percent / S; NaBH₄ / tetrahydrofuran / 1.5 h / Heating

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; borane-THF; ammonium cerium(IV) nitrate; camphor-10-sulfonic acid; hydrogen fluoride; water; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; sulfur; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 7.2: Wittig reaction;
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

: 625450-84-2
3-[(5R)-5-(tert-butyldimethylsilanoxy)-(4S)-4-methoxy-(2R)-2,(6S)-6-dimethyl-oct-7-enyl]-2,4,5-trimethoxyphenylamine

Guidance literature:: Multi-step reaction with 15 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

11.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

12.1: 80 percent / CSA / methanol; CH₂Cl₂ / 2.5 h / 0 °C

13.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 °C

14.1: NaHMDS / diethyl ether / 0 - 20 °C

14.2: 96 mg / diethyl ether / -78 - 20 °C

15.1: 99 percent / S; NaBH₄ / tetrahydrofuran / 1.5 h / Heating

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; borane-THF; Proton Sponge; ammonium cerium(IV) nitrate; camphor-10-sulfonic acid; hydrogen fluoride; water; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; sulfur; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 8.2: Wittig reaction;
DOI:10.1021/jo034870l