(2S,5S,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-hydroxy-1-[(4-methoxybenzyl)oxy]-8-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-2,6,6-trimethyloctan-3-one

Base Information

• Chemical Name: (2S,5S,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-hydroxy-1-[(4-methoxybenzyl)oxy]-8-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-2,6,6-trimethyloctan-3-one
• CAS No.: 1392284-86-4
• Molecular Formula: C₃₃H₅₃NO₇Si
• Molecular Weight: 603.872
• Mol file: 1392284-86-4.mol

Synonyms:(2S,5S,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-hydroxy-1-[(4-methoxybenzyl)oxy]-8-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-2,6,6-trimethyloctan-3-one

Chemical Property of (2S,5S,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-hydroxy-1-[(4-methoxybenzyl)oxy]-8-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-2,6,6-trimethyloctan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-hydroxy-1-[(4-methoxybenzyl)oxy]-8-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-2,6,6-trimethyloctan-3-one

There total 31 articles about (2S,5S,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-hydroxy-1-[(4-methoxybenzyl)oxy]-8-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-2,6,6-trimethyloctan-3-one 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:

(S)-3-((tert-butyldimethylsilyl)oxy)-4-(4-((S)-1-methoxybut-3-en-1-yl)oxazol-2-yl)-2,2-dimethylbutanal (1392284-85-3) + (S)-4-(4-Methoxy-benzyloxy)-3-methyl-butan-2-one (410077-41-7) → (2S,5S,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-hydroxy-1-[(4-methoxybenzyl)oxy]-8-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-2,6,6-trimethyloctan-3-one (1392284-86-4) + (2S,5R,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-hydroxy-1-[(4-methoxybenzyl)oxy]-8-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-2,6,6-trimethyloctan-3-one (1392284-87-5)

Guidance literature:

(S)-4-(4-Methoxy-benzyloxy)-3-methyl-butan-2-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h;

(S)-3-((tert-butyldimethylsilyl)oxy)-4-(4-((S)-1-methoxybut-3-en-1-yl)oxazol-2-yl)-2,2-dimethylbutanal; at -40 ℃; for 0.666667h; Reagent/catalyst; Solvent; Concentration; Overall yield = 95 %; Overall yield = 747 mg;

DOI:10.1055/s-0033-1338493

Reference yield:

methyl 2-(2-(4-methoxybenzyloxy)ethyl)oxazole-4-carboxylate (1414941-33-5) → (2S,5S,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-hydroxy-1-[(4-methoxybenzyl)oxy]-8-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-2,6,6-trimethyloctan-3-one (1392284-86-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / tert-butyl alcohol; water / 1.5 h / 20 °C / Inert atmosphere

2.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / -30 - 20 °C / Inert atmosphere

3.1: diethylamino-sulfur trifluoride / dichloromethane / -78 - 20 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; Bromotrichloromethane / dichloromethane / -78 - 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C / Inert atmosphere

6.1: diethyl ether / 2 h / -100 °C / Inert atmosphere

6.2: 20 °C

7.1: silver(l) oxide / diethyl ether / 18 h / 20 °C / Molecular sieve; Darkness

8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0.42 h / 20 °C / Inert atmosphere

9.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

10.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C

10.2: 0.67 h / -40 °C

With 4-methyl-morpholine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; Bromotrichloromethane; diethylamino-sulfur trifluoride; diisobutylaluminium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; silver(l) oxide; lithium hexamethyldisilazane; isobutyl chloroformate; In tetrahydrofuran; diethyl ether; dichloromethane; water; tert-butyl alcohol;

DOI:10.1055/s-0033-1338493

Reference yield:

(S)-tert-butyl(1-(4-methoxybenzyloxy)-2,2-dimethylhex-5-en-3-yloxy)dimethylsilane (1414941-22-2) → (2S,5S,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-hydroxy-1-[(4-methoxybenzyl)oxy]-8-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-2,6,6-trimethyloctan-3-one (1392284-86-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: ozone; triphenylphosphine / dichloromethane / -78 - 20 °C

2.1: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / tert-butyl alcohol; water / 1.5 h / 20 °C / Inert atmosphere

3.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / -30 - 20 °C / Inert atmosphere

4.1: diethylamino-sulfur trifluoride / dichloromethane / -78 - 20 °C / Inert atmosphere

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; Bromotrichloromethane / dichloromethane / -78 - 20 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C / Inert atmosphere

7.1: diethyl ether / 2 h / -100 °C / Inert atmosphere

7.2: 20 °C

8.1: silver(l) oxide / diethyl ether / 18 h / 20 °C / Molecular sieve; Darkness

9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0.42 h / 20 °C / Inert atmosphere

10.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

11.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C

11.2: 0.67 h / -40 °C

With 4-methyl-morpholine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; Bromotrichloromethane; diethylamino-sulfur trifluoride; diisobutylaluminium hydride; Dess-Martin periodane; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; silver(l) oxide; lithium hexamethyldisilazane; isobutyl chloroformate; In tetrahydrofuran; diethyl ether; dichloromethane; water; tert-butyl alcohol;

DOI:10.1055/s-0033-1338493

upstream raw materials:

(S)-tert-butyl(1-(4-methoxybenzyloxy)-2,2-dimethylhex-5-en-3-yloxy)dimethylsilane

(S)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-4,4-dimethylpentanoic acid

(S)-methyl 2-[2-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)-3,3-dimethylbutyl]oxazole-4-carboxylate

(S)-3-((tert-butyldimethylsilyl)oxy)-4-(4-((S)-1-methoxybut-3-en-1-yl)oxazol-2-yl)-2,2-dimethylbutanal

Downstream raw materials:

C₃₃H₅₅NO₇Si

C₄₀H₆₈BNO₉Si

C₄₀H₆₈BNO₉Si

C₄₈H₈₂INO₁₀Si₂