Acetic acid (2S,4S,6R,8R,10S)-8-[(3S,4R,5S,6S)-4-hydroxy-6-(4-methoxy-benzyloxy)-3,5-dimethyl-2-oxo-octyl]-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester

Base Information

• Chemical Name: Acetic acid (2S,4S,6R,8R,10S)-8-[(3S,4R,5S,6S)-4-hydroxy-6-(4-methoxy-benzyloxy)-3,5-dimethyl-2-oxo-octyl]-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester
• CAS No.: 627511-87-9
• Molecular Formula: C₄₆H₇₂O₁₁Si
• Molecular Weight: 829.157

Synonyms:Acetic acid (2S,4S,6R,8R,10S)-8-[(3S,4R,5S,6S)-4-hydroxy-6-(4-methoxy-benzyloxy)-3,5-dimethyl-2-oxo-octyl]-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester

Chemical Property of Acetic acid (2S,4S,6R,8R,10S)-8-[(3S,4R,5S,6S)-4-hydroxy-6-(4-methoxy-benzyloxy)-3,5-dimethyl-2-oxo-octyl]-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester

Chemical Property:

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Technology Process of Acetic acid (2S,4S,6R,8R,10S)-8-[(3S,4R,5S,6S)-4-hydroxy-6-(4-methoxy-benzyloxy)-3,5-dimethyl-2-oxo-octyl]-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester

There total 19 articles about Acetic acid (2S,4S,6R,8R,10S)-8-[(3S,4R,5S,6S)-4-hydroxy-6-(4-methoxy-benzyloxy)-3,5-dimethyl-2-oxo-octyl]-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-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: 60.0%

(2R,3S)-3-(4-Methoxy-benzyloxy)-2-methyl-pentanal (627511-80-2) + Acetic acid (2S,4S,6R,8R,10S)-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-10-triethylsilanyloxy-8-((Z)-2-trimethylsilanyloxy-but-2-enyl)-1,7-dioxa-spiro[5.5]undec-4-yl ester (627511-79-9) → Acetic acid (2S,4S,6R,8R,10S)-8-[(3S,4R,5S,6S)-4-hydroxy-6-(4-methoxy-benzyloxy)-3,5-dimethyl-2-oxo-octyl]-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester (627511-87-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃;

DOI:10.1016/j.tetlet.2003.08.082

Reference yield:

(S)-2-((S)-2-Benzyloxy-4-trityloxy-butyl)-oxirane (209340-30-7) → Acetic acid (2S,4S,6R,8R,10S)-8-[(3S,4R,5S,6S)-4-hydroxy-6-(4-methoxy-benzyloxy)-3,5-dimethyl-2-oxo-octyl]-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester (627511-87-9)

Guidance literature:

Multi-step reaction with 17 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

16: 89 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

17: 60 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; mercury(II) perchlorate; boron trifluoride diethyl etherate; 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; 17: Mukaiyama aldol reaction;

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 → Acetic acid (2S,4S,6R,8R,10S)-8-[(3S,4R,5S,6S)-4-hydroxy-6-(4-methoxy-benzyloxy)-3,5-dimethyl-2-oxo-octyl]-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester (627511-87-9)

Guidance literature:

Multi-step reaction with 17 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

16: 89 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

17: 60 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; mercury(II) perchlorate; boron trifluoride diethyl etherate; 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; 17: Mukaiyama aldol reaction;

DOI:10.1016/j.tetlet.2003.08.082

upstream raw materials:

(2R,3S)-3-(4-Methoxy-benzyloxy)-2-methyl-pentanal

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

(S)-2-((S)-2-Benzyloxy-4-trityloxy-butyl)-oxirane

2,2-Dimethyl-propionic acid 2-{(2S,4S,6R,8S,10S)-4,10-dihydroxy-8-[2-(4-methoxy-benzyloxy)-ethyl]-4-methyl-1,7-dioxa-spiro[5.5]undec-2-yl}-ethyl ester

Downstream raw materials:

(2S,3R,4S,5S,6S)-1-{(2S,4S,6R,8S,10S)-10-Hydroxy-8-[2-(4-methoxy-benzyloxy)-ethyl]-4-methyl-4-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl}-6-(4-methoxy-benzyloxy)-3,5-dimethyl-octane-2,4-diol

3,3,3-trifluoro-2-methoxy-2-phenyl-propionic acid 1-(3-{10-acetoxy-8-[2-(4-methoxy-benzyloxy)-ethyl]-4-methyl-4-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl}-1-methyl-2-oxo-propyl)-3-(4-methoxy-benzyloxy)-2-methyl-pentyl ester

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