Acetic acid (2S,4S,6R,8R,10S)-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-8-(2-oxo-butyl)-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester

Base Information

Chemical Name:Acetic acid (2S,4S,6R,8R,10S)-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-8-(2-oxo-butyl)-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester
CAS No.:627511-99-3
Molecular Formula:C₃₂H₅₂O₈Si
Molecular Weight:592.846
Hs Code.:

Synonyms:Acetic acid (2S,4S,6R,8R,10S)-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-8-(2-oxo-butyl)-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester

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Chemical Property of Acetic acid (2S,4S,6R,8R,10S)-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-8-(2-oxo-butyl)-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester

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Technology Process of Acetic acid (2S,4S,6R,8R,10S)-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-8-(2-oxo-butyl)-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester

There total 13 articles about Acetic acid (2S,4S,6R,8R,10S)-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-8-(2-oxo-butyl)-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl 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:

: 209340-30-7
(S)-2-((S)-2-Benzyloxy-4-trityloxy-butyl)-oxirane

: 627511-99-3
Acetic acid (2S,4S,6R,8R,10S)-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-8-(2-oxo-butyl)-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 85 percent / n-BuLi; HMPA / tetrahydrofuran / -20 °C

2: DIBALH / CH₂Cl₂; hexane / 20 °C

3: Et₃N / CH₂Cl₂ / 20 °C

4: Hg(ClO₄)2; CaCO₃ / tetrahydrofuran; H₂O / 0 °C

5: 89 percent / aq. HF / acetonitrile / 40 °C

6: H₂ / Pd/C / ethyl acetate / 20 °C

7: PPTS / CH₂Cl₂ / 20 °C

8: 54 percent / PPTS / CH₂Cl₂ / 20 °C

9: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

10: 86 percent / DIBALH / CH₂Cl₂; hexane / -78 °C

11: 92 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 20 °C

12: diethyl ether / 0 °C

13: Dess-Martin periodinane; pyridine / CH₂Cl₂

14: PPTS / CH₂Cl₂; methanol / 0 °C

15: Et₃N; DMAP / CH₂Cl₂ / 20 °C

With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; mercury(II) perchlorate; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; calcium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; acetonitrile;
DOI:10.1016/j.tetlet.2003.08.082

Reference yield:

: tert-Butyl-[(S)-1-[1,3]dithian-2-ylmethyl-1-methyl-2-((R)-2-phenyl-[1,3]dioxan-4-yl)-ethoxy]-dimethyl-silane

: 627511-99-3
Acetic acid (2S,4S,6R,8R,10S)-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-8-(2-oxo-butyl)-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 85 percent / n-BuLi; HMPA / tetrahydrofuran / -20 °C

2: DIBALH / CH₂Cl₂; hexane / 20 °C

3: Et₃N / CH₂Cl₂ / 20 °C

4: Hg(ClO₄)2; CaCO₃ / tetrahydrofuran; H₂O / 0 °C

5: 89 percent / aq. HF / acetonitrile / 40 °C

6: H₂ / Pd/C / ethyl acetate / 20 °C

7: PPTS / CH₂Cl₂ / 20 °C

8: 54 percent / PPTS / CH₂Cl₂ / 20 °C

9: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

10: 86 percent / DIBALH / CH₂Cl₂; hexane / -78 °C

11: 92 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 20 °C

12: diethyl ether / 0 °C

13: Dess-Martin periodinane; pyridine / CH₂Cl₂

14: PPTS / CH₂Cl₂; methanol / 0 °C

15: Et₃N; DMAP / CH₂Cl₂ / 20 °C

With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; mercury(II) perchlorate; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; calcium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; acetonitrile;
DOI:10.1016/j.tetlet.2003.08.082

Reference yield:

: 627511-95-9
2,2-Dimethyl-propionic acid (3S,5S,9S,11S)-3,11-bis-benzyloxy-5,9-dihydroxy-5-methyl-7-oxo-13-trityloxy-tridecyl ester

: 627511-99-3
Acetic acid (2S,4S,6R,8R,10S)-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-8-(2-oxo-butyl)-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1: H₂ / Pd/C / ethyl acetate / 20 °C

2: PPTS / CH₂Cl₂ / 20 °C

3: 54 percent / PPTS / CH₂Cl₂ / 20 °C

4: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

5: 86 percent / DIBALH / CH₂Cl₂; hexane / -78 °C

6: 92 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 20 °C

7: diethyl ether / 0 °C

8: Dess-Martin periodinane; pyridine / CH₂Cl₂

9: PPTS / CH₂Cl₂; methanol / 0 °C

10: Et₃N; DMAP / CH₂Cl₂ / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; palladium on activated charcoal; In methanol; diethyl ether; hexane; dichloromethane; ethyl acetate;
DOI:10.1016/j.tetlet.2003.08.082