ethyl (5S^,6S^)-6-benzyloxy-5-tert-butyldimethylsilyloxy-3-oxodecanoate

Base Information

Chemical Name:ethyl (5S^*,6S^*)-6-benzyloxy-5-tert-butyldimethylsilyloxy-3-oxodecanoate
CAS No.:136864-77-2
Molecular Formula:C₂₅H₄₂O₅Si
Molecular Weight:450.691
Hs Code.:

ethyl (5S<sup>*</sup>,6S<sup>*</sup>)-6-benzyloxy-5-tert-butyldimethylsilyloxy-3-oxodecanoate

Synonyms:ethyl (5S^*,6S^*)-6-benzyloxy-5-tert-butyldimethylsilyloxy-3-oxodecanoate

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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 ethyl (5S^*,6S^*)-6-benzyloxy-5-tert-butyldimethylsilyloxy-3-oxodecanoate

Chemical Property:

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Technology Process of ethyl (5S^*,6S^*)-6-benzyloxy-5-tert-butyldimethylsilyloxy-3-oxodecanoate

There total 10 articles about ethyl (5S^*,6S^*)-6-benzyloxy-5-tert-butyldimethylsilyloxy-3-oxodecanoate 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: 94.0%

: 623-73-4
diazoacetic acid ethyl ester

: 136850-71-0
(3S^*,4S^*)-4-benzyloxy-3-tert-butyldimethylsilyloxyoctanal

: 136864-77-2
ethyl (5S^*,6S^*)-6-benzyloxy-5-tert-butyldimethylsilyloxy-3-oxodecanoate

Guidance literature:: With tin(ll) chloride; In dichloromethane; for 4h; Ambient temperature;
DOI:10.1248/cpb.39.1866

Reference yield:

: methoxymethyl 5-crotyltetronate

: 136864-77-2
ethyl (5S^*,6S^*)-6-benzyloxy-5-tert-butyldimethylsilyloxy-3-oxodecanoate

Guidance literature:: Multi-step reaction with 11 steps

1: 75.9 percent / H₂ / 5percent rhodium on alumina / ethyl acetate / 4 h / 5320 Torr

2: 97.7 percent / lithium aluminium hydride / diethyl ether / 2 h / Ambient temperature

3: 78.3 percent / triethylamine / benzene / 6 h / Ambient temperature

4: NaH (60percent oil dispersion) / tetrahydrofuran / 6 h

5: tetrabutylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature

6: 95.1 percent / pyridine / tetrahydrofuran / 2 h / Ambient temperature

7: 81.9 percent / 10percent HCl / tetrahydrofuran / 2 h / Heating

8: 85.9 percent / imidazole / tetrahydrofuran / 6 h / Ambient temperature

9: 86.7 percent / 10percent aq. NaOH / methanol / 2 h / Ambient temperature

10: 91 percent / pyridinium chlorochromate (PCC), sodium acetate / CH₂Cl₂ / 1 h / Ambient temperature

11: 94 percent / SnCl₂ / CH₂Cl₂ / 4 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; sodium hydride; triethylamine; pyridinium chlorochromate; tin(ll) chloride; Rh/Al₂O₃; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; benzene;
DOI:10.1248/cpb.39.1866

Reference yield:

: 136850-66-3
(3S^*,4S^*)-1-tert-butyldimethylsilyloxy-4-dihydroxy-3-methoxymethoxyoctane

: 136864-77-2
ethyl (5S^*,6S^*)-6-benzyloxy-5-tert-butyldimethylsilyloxy-3-oxodecanoate

Guidance literature:: Multi-step reaction with 8 steps

1: NaH (60percent oil dispersion) / tetrahydrofuran / 6 h

2: tetrabutylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature

3: 95.1 percent / pyridine / tetrahydrofuran / 2 h / Ambient temperature

4: 81.9 percent / 10percent HCl / tetrahydrofuran / 2 h / Heating

5: 85.9 percent / imidazole / tetrahydrofuran / 6 h / Ambient temperature

6: 86.7 percent / 10percent aq. NaOH / methanol / 2 h / Ambient temperature

7: 91 percent / pyridinium chlorochromate (PCC), sodium acetate / CH₂Cl₂ / 1 h / Ambient temperature

8: 94 percent / SnCl₂ / CH₂Cl₂ / 4 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; sodium hydroxide; tetrabutyl ammonium fluoride; sodium acetate; sodium hydride; pyridinium chlorochromate; tin(ll) chloride; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1248/cpb.39.1866