(2E,9E)-(4S,6S,7R,8R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11-(4-methoxy-benzyloxy)-3,7,9-trimethyl-undeca-2,9-dienal

Base Information

Chemical Name:(2E,9E)-(4S,6S,7R,8R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11-(4-methoxy-benzyloxy)-3,7,9-trimethyl-undeca-2,9-dienal
CAS No.:147438-52-6
Molecular Formula:C₃₅H₆₂O₆Si₂
Molecular Weight:635.045
Hs Code.:

Synonyms:(2E,9E)-(4S,6S,7R,8R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11-(4-methoxy-benzyloxy)-3,7,9-trimethyl-undeca-2,9-dienal

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Chemical Property of (2E,9E)-(4S,6S,7R,8R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11-(4-methoxy-benzyloxy)-3,7,9-trimethyl-undeca-2,9-dienal

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Technology Process of (2E,9E)-(4S,6S,7R,8R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11-(4-methoxy-benzyloxy)-3,7,9-trimethyl-undeca-2,9-dienal

There total 17 articles about (2E,9E)-(4S,6S,7R,8R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11-(4-methoxy-benzyloxy)-3,7,9-trimethyl-undeca-2,9-dienal 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: 97.0%

: (2E,9E)-(4S,6S,7R,8R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11-(4-methoxy-benzyloxy)-3,7,9-trimethyl-undeca-2,9-dien-1-ol

: 147438-52-6
(2E,9E)-(4S,6S,7R,8R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11-(4-methoxy-benzyloxy)-3,7,9-trimethyl-undeca-2,9-dienal

Guidance literature:: With manganese(IV) oxide; In dichloromethane; for 0.5h; Ambient temperature;
DOI:10.1016/S0040-4039(00)77485-5

Reference yield:

: ((S)-4-Benzyloxymethoxy-1,3-dimethyl-2-oxo-butyl)-phosphonic acid diethyl ester

: 147438-52-6
(2E,9E)-(4S,6S,7R,8R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11-(4-methoxy-benzyloxy)-3,7,9-trimethyl-undeca-2,9-dienal

Guidance literature:: Multi-step reaction with 16 steps

1: 100 percent / H₂ / Pd / ethanol / 12 h / Ambient temperature

2: 72 percent / LiCl, DIPEA / acetonitrile / 24 h / Ambient temperature

3: 94 percent / Zn(BH₄)2 / diethyl ether / 0.5 h / 0 °C

4: 97 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

5: 100 percent / NaH / tetrahydrofuran / 12 h / Ambient temperature

6: 97 percent / CSA / methanol; CH₂Cl₂ / 12 h / Ambient temperature

7: 98 percent / (COCl)2, DMSO, DIPEA / CH₂Cl₂ / -60 °C

8: 92 percent / LDA / tetrahydrofuran / 0.33 h / -78 °C

9: 88 percent / (COCl)2, DMSO, DIPEA / CH₂Cl₂ / -60 °C

10: L-Selectride / tetrahydrofuran / 0.5 h / -78 °C

11: 1) t-butyllithium / 1) pentane, Et₂O, TFF, -100 deg C, 2) -100 deg C --> -78 deg C, 20 min

12: 1) Me₄NBH(OAc)3, 2) ppTs / 1) CH₃CN, Ac₂OH, -20 deg C, 24 h, 2) MeOH, room temperature, 12 h

13: 90 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

14: 81 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

15: 99 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

16: 97 percent / MnO₂ / CH₂Cl₂ / 0.5 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; manganese(IV) oxide; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; L-Selectride; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; lithium chloride; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; palladium; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(00)77485-5

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 147438-52-6
(2E,9E)-(4S,6S,7R,8R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11-(4-methoxy-benzyloxy)-3,7,9-trimethyl-undeca-2,9-dienal

Guidance literature:: Multi-step reaction with 3 steps

1: 81 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

2: 99 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

3: 97 percent / MnO₂ / CH₂Cl₂ / 0.5 h / Ambient temperature

With 2,6-dimethylpyridine; manganese(IV) oxide; lithium aluminium tetrahydride; In diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(00)77485-5