(E)-(2S,4S,5R,6S,9S,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-1-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,5,10-trimethoxy-2,6,8-trimethyl-dodeca-7,11-dien-1-one

Base Information

Chemical Name:(E)-(2S,4S,5R,6S,9S,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-1-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,5,10-trimethoxy-2,6,8-trimethyl-dodeca-7,11-dien-1-one
CAS No.:145798-87-4
Molecular Formula:C₅₁H₆₉NO₇Si
Molecular Weight:836.197
Hs Code.:

(E)-(2S,4S,5R,6S,9S,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-1-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,5,10-trimethoxy-2,6,8-trimethyl-dodeca-7,11-dien-1-one

Synonyms:(E)-(2S,4S,5R,6S,9S,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-1-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,5,10-trimethoxy-2,6,8-trimethyl-dodeca-7,11-dien-1-one

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Chemical Property of (E)-(2S,4S,5R,6S,9S,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-1-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,5,10-trimethoxy-2,6,8-trimethyl-dodeca-7,11-dien-1-one

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Technology Process of (E)-(2S,4S,5R,6S,9S,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-1-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,5,10-trimethoxy-2,6,8-trimethyl-dodeca-7,11-dien-1-one

There total 14 articles about (E)-(2S,4S,5R,6S,9S,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-1-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,5,10-trimethoxy-2,6,8-trimethyl-dodeca-7,11-dien-1-one 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%

: 137822-30-1
(1S,2S,4S,5R,6S,7E,9S,10S)-9-<(t-butyldimethylsilyl)oxy>-1-<2,5-dimethoxy-3-<(triphenylmethyl)amino>phenyl>-4,5,10-trimethoxy-2,6,8-trimethyl-7,11-dodecadien-1-ol

: 145798-87-4
(E)-(2S,4S,5R,6S,9S,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-1-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,5,10-trimethoxy-2,6,8-trimethyl-dodeca-7,11-dien-1-one

Guidance literature:: With acetic anhydride; dimethyl sulfoxide; at 95 ℃; for 0.5h;
DOI:10.1016/S0040-4039(00)79452-4

Reference yield:

: 115929-62-9
3-bromo-2,5-dimethoxyaniline

: 145798-87-4
(E)-(2S,4S,5R,6S,9S,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-1-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,5,10-trimethoxy-2,6,8-trimethyl-dodeca-7,11-dien-1-one

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / NEt₃ / CH₂Cl₂ / 24 h / Ambient temperature

2: 1.) butyllithium / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) THF, -78 deg C, 2 h

3: 80 percent / DMSO-acetic anhydride / 0.5 h / 95 °C

With n-butyllithium; acetic anhydride; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1246/bcsj.65.2974

Reference yield:

: 137788-14-8,145842-39-3
(2S,3R,4S,6S)-3,4-dimethoxy-7-<(4-methoxybenzyl)oxy>-2,6-dimethyl-1-heptanol

: 145798-87-4
(E)-(2S,4S,5R,6S,9S,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-1-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,5,10-trimethoxy-2,6,8-trimethyl-dodeca-7,11-dien-1-one

Guidance literature:: Multi-step reaction with 8 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / Ambient temperature

2: 1.) s-butyllithium / 1.) THF, cyclohexane, RT, 0.5 h, 2.) THF, cyclohexane, from -78 deg C to -20 deg C, 4.5 h

3: 1.) s-BuLi, 2.) (+)-B-methoxydiisopinocampheylborane, 3.) BF₃*Et₂O

4: 91 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

5: 97 percent / DDQ / CH₂Cl₂; H₂O / 1 h / Ambient temperature

6: 88 percent / oxalyl dichloride, DMSO / CH₂Cl₂ / 0.25 h / -78 °C

7: 1.) butyllithium / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) THF, -78 deg C, 2 h

8: 80 percent / DMSO-acetic anhydride / 0.5 h / 95 °C

With (+)-Ipc₂BOMe; 1H-imidazole; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; sec.-butyllithium; acetic anhydride; Dess-Martin periodane; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.65.2974