(3S,5R)-7-Benzyloxy-3-hydroxy-5-trimethylsilanyloxy-heptanoic acid ethyl ester

Base Information

Chemical Name:(3S,5R)-7-Benzyloxy-3-hydroxy-5-trimethylsilanyloxy-heptanoic acid ethyl ester
CAS No.:309755-04-2
Molecular Formula:C₁₉H₃₂O₅Si
Molecular Weight:368.546
Hs Code.:

Synonyms:(3S,5R)-7-Benzyloxy-3-hydroxy-5-trimethylsilanyloxy-heptanoic acid ethyl ester

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Chemical Property of (3S,5R)-7-Benzyloxy-3-hydroxy-5-trimethylsilanyloxy-heptanoic acid ethyl ester

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Technology Process of (3S,5R)-7-Benzyloxy-3-hydroxy-5-trimethylsilanyloxy-heptanoic acid ethyl ester

There total 6 articles about (3S,5R)-7-Benzyloxy-3-hydroxy-5-trimethylsilanyloxy-heptanoic acid ethyl 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:

: 19790-60-4
3-Benzyloxypropanal

: 309755-04-2
(3S,5R)-7-Benzyloxy-3-hydroxy-5-trimethylsilanyloxy-heptanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 68 percent / (S)-oxazaborolidinone derived from BH₃*THF, N-Ts-L-valine / CH₂Cl₂ / 20 h / -78 °C

2: 95 percent / n-Bu₃SnH; AIBN

3: 85 percent / 2,6-lutidine

4: 72 percent / DIBALH / CH₂Cl₂ / -78 °C

5: 65 percent / (R)-oxazaborolidinone derived from BH₃*THF, N-Ts-D-valine / CH₂Cl₂ / 20 h / -78 °C

6: n-Bu₃SnH; AIBN

With 2,6-dimethylpyridine; N-(p-toluenesulfonyl)-L-valine; 2,2'-azobis(isobutyronitrile); (R)-oxazaborolidinone derived from BH₃*THF; (S)-oxazaborolidinone derived from BH₃*THF; N-((4-methylphenyl)sulfonyl)-D-valine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; In dichloromethane; 1: aldol reaction / 2: desulfurization / 3: Etherification / 4: Reduction / 5: aldol reaction / 6: desulfurization;
DOI:10.1016/S0040-4039(00)01289-2

Reference yield:

: 113335-04-9
(R)-5-Benzyloxy-3-hydroxy-pentanoic acid ethyl ester

: 309755-04-2
(3S,5R)-7-Benzyloxy-3-hydroxy-5-trimethylsilanyloxy-heptanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / 2,6-lutidine

2: 72 percent / DIBALH / CH₂Cl₂ / -78 °C

3: 65 percent / (R)-oxazaborolidinone derived from BH₃*THF, N-Ts-D-valine / CH₂Cl₂ / 20 h / -78 °C

4: n-Bu₃SnH; AIBN

With 2,6-dimethylpyridine; 2,2'-azobis(isobutyronitrile); (R)-oxazaborolidinone derived from BH₃*THF; N-((4-methylphenyl)sulfonyl)-D-valine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; In dichloromethane; 1: Etherification / 2: Reduction / 3: aldol reaction / 4: desulfurization;
DOI:10.1016/S0040-4039(00)01289-2

Reference yield:

: 309755-03-1
(R)-5-Benzyloxy-3-trimethylsilanyloxy-pentanal

: 309755-04-2
(3S,5R)-7-Benzyloxy-3-hydroxy-5-trimethylsilanyloxy-heptanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 65 percent / (R)-oxazaborolidinone derived from BH₃*THF, N-Ts-D-valine / CH₂Cl₂ / 20 h / -78 °C

2: n-Bu₃SnH; AIBN

With 2,2'-azobis(isobutyronitrile); (R)-oxazaborolidinone derived from BH₃*THF; N-((4-methylphenyl)sulfonyl)-D-valine; tri-n-butyl-tin hydride; In dichloromethane; 1: aldol reaction / 2: desulfurization;
DOI:10.1016/S0040-4039(00)01289-2