(4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4-methyl-heptanal

Base Information

Chemical Name:(4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4-methyl-heptanal
CAS No.:178113-96-7
Molecular Formula:C₂₂H₃₈O₄Si
Molecular Weight:394.627
Hs Code.:

Synonyms:(4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4-methyl-heptanal

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4-methyl-heptanal

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Technology Process of (4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4-methyl-heptanal

There total 8 articles about (4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4-methyl-heptanal 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: 85.0%

: 178113-95-6
(4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4-methyl-heptanoic acid methyl ester

: 178113-96-7
(4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4-methyl-heptanal

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; toluene; at -80 ℃; for 0.833333h;
DOI:10.1055/s-1996-4254

Reference yield:

: 105198-38-7,106513-42-2
ethyl (S)-2-(tert-butyldimethylsilyloxy)propanoate

: 178113-96-7
(4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4-methyl-heptanal

Guidance literature:: Multi-step reaction with 7 steps

1: 85 percent / DIBALH / toluene; CH₂Cl₂ / 0.58 h / -80 °C

2: 1.) (-)-sparteine, BuLi, 2.) Ti(i-PrO)4

3: 66 percent / TMSOTf / diethyl ether / 2 h / Ambient temperature

4: 81 percent / t-BuLi / diethyl ether / 0.5 h / -20 °C

5: 1.) BuLi / 1.) THF, hexane, -80 deg C, 40 min, 2.) THF, hexane, a) from -80 deg C to -35 deg C, 45 min, b) RT, 90 min

6: 84 percent / H₂ / 5percent Pd/C / ethyl acetate / 2 h / 760 Torr

7: 85 percent / DIBALH / CH₂Cl₂; toluene / 0.83 h / -80 °C

With titanium(IV) isopropylate; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; (-)-sparteine; palladium on activated charcoal; In diethyl ether; dichloromethane; ethyl acetate; toluene;
DOI:10.1055/s-1996-4254

Reference yield:

: 87727-28-4
(S)-2-tert-butyl-dimethyl-silanyloxy propanal

: 178113-96-7
(4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4-methyl-heptanal

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) (-)-sparteine, BuLi, 2.) Ti(i-PrO)4

2: 66 percent / TMSOTf / diethyl ether / 2 h / Ambient temperature

3: 81 percent / t-BuLi / diethyl ether / 0.5 h / -20 °C

4: 1.) BuLi / 1.) THF, hexane, -80 deg C, 40 min, 2.) THF, hexane, a) from -80 deg C to -35 deg C, 45 min, b) RT, 90 min

5: 84 percent / H₂ / 5percent Pd/C / ethyl acetate / 2 h / 760 Torr

6: 85 percent / DIBALH / CH₂Cl₂; toluene / 0.83 h / -80 °C

With titanium(IV) isopropylate; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; (-)-sparteine; palladium on activated charcoal; In diethyl ether; dichloromethane; ethyl acetate; toluene;
DOI:10.1055/s-1996-4254