2,2-Dimethyl-propionic acid (3S,5S,9S,11S)-3,11-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-5-methyl-7-oxo-13-trityloxy-tridecyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (3S,5S,9S,11S)-3,11-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-5-methyl-7-oxo-13-trityloxy-tridecyl ester
• CAS No.: 627511-83-5
• Molecular Formula: C₅₈H₇₆O₈Si
• Molecular Weight: 929.322

Synonyms:2,2-Dimethyl-propionic acid (3S,5S,9S,11S)-3,11-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-5-methyl-7-oxo-13-trityloxy-tridecyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (3S,5S,9S,11S)-3,11-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-5-methyl-7-oxo-13-trityloxy-tridecyl ester

Chemical Property:

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Technology Process of 2,2-Dimethyl-propionic acid (3S,5S,9S,11S)-3,11-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-5-methyl-7-oxo-13-trityloxy-tridecyl ester

There total 3 articles about 2,2-Dimethyl-propionic acid (3S,5S,9S,11S)-3,11-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-5-methyl-7-oxo-13-trityloxy-tridecyl 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:

2,2-Dimethyl-propionic acid (3S,5S)-3-benzyloxy-6-[2-((2S,4S)-4-benzyloxy-2-hydroxy-6-trityloxy-hexyl)-[1,3]dithian-2-yl]-5-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexyl ester → 2,2-Dimethyl-propionic acid (3S,5S,9S,11S)-3,11-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-5-methyl-7-oxo-13-trityloxy-tridecyl ester (627511-83-5)

Guidance literature:

With mercury(II) perchlorate; calcium carbonate; In tetrahydrofuran; water; at 0 ℃;

DOI:10.1016/j.tetlet.2003.08.082

Reference yield:

(S)-2-((S)-2-Benzyloxy-4-trityloxy-butyl)-oxirane (209340-30-7) → 2,2-Dimethyl-propionic acid (3S,5S,9S,11S)-3,11-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-5-methyl-7-oxo-13-trityloxy-tridecyl ester (627511-83-5)

Guidance literature:

Multi-step reaction with 4 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

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; mercury(II) perchlorate; diisobutylaluminium hydride; triethylamine; calcium carbonate; In tetrahydrofuran; hexane; dichloromethane; water;

DOI:10.1016/j.tetlet.2003.08.082

Reference yield:

(2S,4S)-4-Benzyloxy-1-{2-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3-((R)-2-phenyl-[1,3]dioxan-4-yl)-propyl]-[1,3]dithian-2-yl}-6-trityloxy-hexan-2-ol → 2,2-Dimethyl-propionic acid (3S,5S,9S,11S)-3,11-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-5-methyl-7-oxo-13-trityloxy-tridecyl ester (627511-83-5)

Guidance literature:

Multi-step reaction with 3 steps

1: DIBALH / CH₂Cl₂; hexane / 20 °C

2: Et₃N / CH₂Cl₂ / 20 °C

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

With mercury(II) perchlorate; diisobutylaluminium hydride; triethylamine; calcium carbonate; In tetrahydrofuran; hexane; dichloromethane; water;

DOI:10.1016/j.tetlet.2003.08.082

upstream raw materials:

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

Downstream raw materials:

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

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

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

{(2R,4S,6R,8S,10S)-8-[2-(4-Methoxy-benzyloxy)-ethyl]-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl}-acetaldehyde

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