C₂₇H₃₈O₆Si

Base Information

• Chemical Name: C₂₇H₃₈O₆Si
• CAS No.: 1132970-07-0
• Molecular Formula: C₂₇H₃₈O₆Si
• Molecular Weight: 486.681
• Mol file: 1132970-07-0.mol

Synonyms:C₂₇H₃₈O₆Si

Chemical Property of C₂₇H₃₈O₆Si

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₂₇H₃₈O₆Si

There total 14 articles about C₂₇H₃₈O₆Si 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%

(R)-4-((1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-1-hydroxy-2,4-dimethyl-3-oxohexyl)-1,3-dioxolan-2-one (1132969-96-0) → (R)-4-((1R,2S,3R,4S,5S)-5-(tert-butyldiphenylsilyloxy)-1,3-dihydroxy-2,4-dimethylhexyl)-1,3-dioxolan-2-one (1132970-08-1) + C27H38O6Si (1132970-07-0)

Guidance literature:

With acetic acid; tetramethylammonium triacetoxyborohydride; In acetonitrile; at -10 - -5 ℃; Inert atmosphere;

DOI:10.1002/anie.200804645

Reference yield:

(R)-4-benzyl-3-((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanoyl)oxazolidin-2-one (1379802-66-0) → C27H38O6Si (1132970-07-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: lithium borohydride / tetrahydrofuran; diethyl ether; ethanol / 4.5 h / 0 - 20 °C / Inert atmosphere

2.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; potassium bromide / dichloromethane / 0 °C / pH 8.6 / aq. buffer

2.2: 0.42 h / 0 °C

3.1: hydroxylamine hydrochloride / pyridine; ethanol / 12.5 h / 20 °C / Inert atmosphere

4.1: dichloromethane / -78 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / methanol / 1.75 h / 20 °C / Inert atmosphere

6.1: pyridine / dichloromethane / 0.17 h / -78 - 0 °C / Inert atmosphere

7.1: hydrogen; boric acid / methanol; water / 3 h / 20 °C

8.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 118 h / -10 - -5 °C / Inert atmosphere

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium borohydride; hydroxylamine hydrochloride; hydrogen; boric acid; toluene-4-sulfonic acid; acetic acid; potassium bromide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1002/chem.201102797

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → C27H38O6Si (1132970-07-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 44 h / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / 0 °C / Inert atmosphere

2.2: 1.75 h / 0 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane / 1.75 h / -78 - -40 °C / Inert atmosphere

4.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; potassium bromide / dichloromethane / 0 °C / pH 8.6 / aq. buffer

4.2: 0.42 h / 0 °C

5.1: hydroxylamine hydrochloride / pyridine; ethanol / 12.5 h / 20 °C / Inert atmosphere

6.1: dichloromethane / -78 °C / Inert atmosphere

6.2: 0 - 20 °C / Inert atmosphere

7.1: toluene-4-sulfonic acid / methanol / 1.75 h / 20 °C / Inert atmosphere

8.1: pyridine / dichloromethane / 0.17 h / -78 - 0 °C / Inert atmosphere

9.1: hydrogen; boric acid / methanol; water / 3 h / 20 °C

10.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 118 h / -10 - -5 °C / Inert atmosphere

With pyridine; 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; n-butyllithium; hydroxylamine hydrochloride; hydrogen; boric acid; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; potassium bromide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; pyridine; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/chem.201102797

upstream raw materials:

(R)-4-((1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-1-hydroxy-2,4-dimethyl-3-oxohexyl)-1,3-dioxolan-2-one

(2S,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanal oxime

(S,Z)-1-(trityloxy)pent-3-en-2-ol

(R)-1-((4S,5R)-3-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-4-methyl-4,5-dihydroisoxazol-5-yl)-2-(trityloxy)ethanol

Downstream raw materials:

(R)-1-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)ethane-1,2-diol

(4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxane-4-carbaldehyde

methyl (2Z,4E,6R,7S,8S,10E,14S)-14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-14-hydroxy-2-methoxy-4,6,8,10-tetramethyl-7-(triethylsilyloxy)tetradeca-2,4,10-trien-12-ynoate

(2Z,4E,6R,7S,8S,10E,12E,14S)-methyl 14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-7-hydroxy-2,14-dimethoxy-4,6,8,10-tetramethyltetradeca-2,4,10,12-tetraenoate

Refernces

• 1、 Kleinbeck, Florian,Carreira, Erick M.. "Total synthesis of bafilomycin A1". supporting information; experimental part. p. 578 - 581. Retrieved 2009/04/14.