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

Base Information

Chemical Name:(4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4-methyl-hept-2-ynoic acid methyl ester
CAS No.:178113-94-5
Molecular Formula:C₂₃H₃₆O₅Si
Molecular Weight:420.621
Hs Code.:

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

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Chemical Property of (4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4-methyl-hept-2-ynoic acid methyl ester

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Technology Process of (4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4-methyl-hept-2-ynoic acid methyl ester

There total 6 articles about (4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4-methyl-hept-2-ynoic 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:

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

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

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

With titanium(IV) isopropylate; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; tert.-butyl lithium; (-)-sparteine; In diethyl ether;
DOI:10.1055/s-1996-4254

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

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

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / imidazole, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

2: 85 percent / DIBALH / toluene; CH₂Cl₂ / 0.58 h / -80 °C

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

4: 66 percent / TMSOTf / diethyl ether / 2 h / Ambient temperature

5: 81 percent / t-BuLi / diethyl ether / 0.5 h / -20 °C

6: 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

With 1H-imidazole; titanium(IV) isopropylate; dmap; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; tert.-butyl lithium; diisobutylaluminium hydride; (-)-sparteine; In diethyl ether; dichloromethane; toluene;
DOI:10.1055/s-1996-4254