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

Base Information

Chemical Name:(4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4-methyl-heptanoic acid methyl ester
CAS No.:178113-95-6
Molecular Formula:C₂₃H₄₀O₅Si
Molecular Weight:424.653
Hs Code.:

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

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

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

There total 7 articles about (4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4-methyl-heptanoic acid methyl ester 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: 84.0%

: 178113-94-5
(4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4-methyl-hept-2-ynoic acid methyl ester

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

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; for 2h; under 760 Torr;
DOI:10.1055/s-1996-4254

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

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

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

Guidance literature:: Multi-step reaction with 5 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

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