(E)-(2R,3S,6S,7R,8S,10S,11R)-3-(tert-Butyl-dimethyl-silanyloxy)-11-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-2,7,8,11-tetramethoxy-4,6,10-trimethyl-undec-4-enal

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Chemical Name:(E)-(2R,3S,6S,7R,8S,10S,11R)-3-(tert-Butyl-dimethyl-silanyloxy)-11-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-2,7,8,11-tetramethoxy-4,6,10-trimethyl-undec-4-enal
CAS No.:137788-18-2
Molecular Formula:C₅₁H₇₁NO₈Si
Molecular Weight:854.212
Hs Code.:

(E)-(2R,3S,6S,7R,8S,10S,11R)-3-(tert-Butyl-dimethyl-silanyloxy)-11-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-2,7,8,11-tetramethoxy-4,6,10-trimethyl-undec-4-enal

Synonyms:(E)-(2R,3S,6S,7R,8S,10S,11R)-3-(tert-Butyl-dimethyl-silanyloxy)-11-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-2,7,8,11-tetramethoxy-4,6,10-trimethyl-undec-4-enal

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Chemical Property of (E)-(2R,3S,6S,7R,8S,10S,11R)-3-(tert-Butyl-dimethyl-silanyloxy)-11-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-2,7,8,11-tetramethoxy-4,6,10-trimethyl-undec-4-enal

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Technology Process of (E)-(2R,3S,6S,7R,8S,10S,11R)-3-(tert-Butyl-dimethyl-silanyloxy)-11-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-2,7,8,11-tetramethoxy-4,6,10-trimethyl-undec-4-enal

There total 14 articles about (E)-(2R,3S,6S,7R,8S,10S,11R)-3-(tert-Butyl-dimethyl-silanyloxy)-11-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-2,7,8,11-tetramethoxy-4,6,10-trimethyl-undec-4-enal 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: 76.0%

: 145798-94-3
{3-[(E)-(1R,2S,4S,5R,6S,9S,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-1,4,5,10-tetramethoxy-2,6,8-trimethyl-dodeca-7,11-dienyl]-2,5-dimethoxy-phenyl}-trityl-amine

: 137788-18-2
(E)-(2R,3S,6S,7R,8S,10S,11R)-3-(tert-Butyl-dimethyl-silanyloxy)-11-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-2,7,8,11-tetramethoxy-4,6,10-trimethyl-undec-4-enal

Guidance literature:: With sodium periodate; osmium(VIII) oxide; phosphate buffer; In tetrahydrofuran; for 16h; Ambient temperature;
DOI:10.1246/bcsj.65.2974

Reference yield:

: (E)-(3S,4S,7S,8R,9S,11S,12R)-4-(tert-Butyl-dimethyl-silanyloxy)-12-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-3,8,9,12-tetramethoxy-5,7,11-trimethyl-dodec-5-ene-1,2-diol

: 137788-18-2
(E)-(2R,3S,6S,7R,8S,10S,11R)-3-(tert-Butyl-dimethyl-silanyloxy)-11-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-2,7,8,11-tetramethoxy-4,6,10-trimethyl-undec-4-enal

Guidance literature:: With lead(IV) acetate; potassium acetate; In acetonitrile; at 0 ℃; for 0.5h; Yield given;
DOI:10.1246/bcsj.65.2974

Reference yield:

: 137788-15-9
(2E,4S,5R,6S,8S)-5,6-dimethoxy-9-<(4-methoxybenzyl)oxy>-2,4,8-trimethyl-2-nonenal

: 137788-18-2
(E)-(2R,3S,6S,7R,8S,10S,11R)-3-(tert-Butyl-dimethyl-silanyloxy)-11-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-2,7,8,11-tetramethoxy-4,6,10-trimethyl-undec-4-enal

Guidance literature:: Multi-step reaction with 7 steps

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

2: 91 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

3: 97 percent / DDQ / CH₂Cl₂; H₂O / 1 h / Ambient temperature

4: 88 percent / oxalyl dichloride, DMSO / CH₂Cl₂ / 0.25 h / -78 °C

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

6: 100 percent / NaH / dimethylformamide / 6.5 h / 0 °C

7: 76 percent / OsO₄-NaIO₄, phosphate buffer / tetrahydrofuran / 16 h / Ambient temperature

With (+)-Ipc₂BOMe; 1H-imidazole; sodium periodate; osmium(VIII) oxide; n-butyllithium; phosphate buffer; oxalyl dichloride; boron trifluoride diethyl etherate; sec.-butyllithium; sodium hydride; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.65.2974