Carbonic acid (S)-1-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5-(4-methoxy-benzyloxy)-4-methyl-pent-2-ynyl ester methyl ester

Base Information

• Chemical Name: Carbonic acid (S)-1-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5-(4-methoxy-benzyloxy)-4-methyl-pent-2-ynyl ester methyl ester
• CAS No.: 714974-23-9
• Molecular Formula: C₃₈H₅₀O₆Si
• Molecular Weight: 630.897
• Mol file: 714974-23-9.mol

Synonyms:Carbonic acid (S)-1-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5-(4-methoxy-benzyloxy)-4-methyl-pent-2-ynyl ester methyl ester

Chemical Property of Carbonic acid (S)-1-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5-(4-methoxy-benzyloxy)-4-methyl-pent-2-ynyl ester methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbonic acid (S)-1-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5-(4-methoxy-benzyloxy)-4-methyl-pent-2-ynyl ester methyl ester

There total 5 articles about Carbonic acid (S)-1-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5-(4-methoxy-benzyloxy)-4-methyl-pent-2-ynyl ester methyl 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:

methyl chloroformate (79-22-1) + (2R,4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-2,4-dimethylpentanal (157837-65-5) + (S)-1-(((4,4-dibromo-2-methylbut-3-en-1-yl)oxy)methyl)-4-methoxybenzene (570394-37-5) → Carbonic acid (S)-1-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5-(4-methoxy-benzyloxy)-4-methyl-pent-2-ynyl ester methyl ester (714974-23-9)

Guidance literature:

(S)-1-(((4,4-dibromo-2-methylbut-3-en-1-yl)oxy)methyl)-4-methoxybenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -40 ℃; for 1h;

(2R,4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-2,4-dimethylpentanal; In tetrahydrofuran; hexane; at -30 ℃; for 1h;

methyl chloroformate; In tetrahydrofuran; hexane; at -20 ℃;

DOI:10.1021/ol049356w

Reference yield:

(2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate (90270-02-3,97937-36-5) → Carbonic acid (S)-1-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5-(4-methoxy-benzyloxy)-4-methyl-pent-2-ynyl ester methyl ester (714974-23-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 98 percent / imidazole / CH₂Cl₂ / 0.5 h / 20 °C

2.1: 98 percent / potassium carbonate / methanol / 2 h / 20 °C

3.1: imidazole / dimethylformamide / 0 - 20 °C

3.2: 97 percent / PPTS / ethanol / 7 h / 50 °C

4.1: 88 percent / N-methylmorpholine N-oxide; tetrapropylammonium perruthenate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 20 °C

5.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 - -40 °C

5.2: hexane; tetrahydrofuran / 1 h / -30 °C

5.3: hexane; tetrahydrofuran / -20 °C

With 1H-imidazole; n-butyllithium; tetrapropylammonium perruthennate; 4 A molecular sieve; potassium carbonate; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol049356w

Reference yield:

(2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol (147782-80-7) → Carbonic acid (S)-1-[(1R,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5-(4-methoxy-benzyloxy)-4-methyl-pent-2-ynyl ester methyl ester (714974-23-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: imidazole / dimethylformamide / 0 - 20 °C

1.2: 97 percent / PPTS / ethanol / 7 h / 50 °C

2.1: 88 percent / N-methylmorpholine N-oxide; tetrapropylammonium perruthenate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 20 °C

3.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 - -40 °C

3.2: hexane; tetrahydrofuran / 1 h / -30 °C

3.3: hexane; tetrahydrofuran / -20 °C

With 1H-imidazole; n-butyllithium; tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol049356w

upstream raw materials:

methyl chloroformate

(2R,4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-2,4-dimethylpentanal

(S)-1-(((4,4-dibromo-2-methylbut-3-en-1-yl)oxy)methyl)-4-methoxybenzene

(2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate

Downstream raw materials:

(1''S,1'''R,2'''R,3S,4S,6S,8R,10S)-3-(tert-butyldimethyl-silyloxy)-4,6,8,10-tetramethyl-11-(tetrahydropyran-2'-yloxy)undecanoic acid 6''-bromo-6''-cyano-1-[2'''-(4'''-methoxymenzyloxymethyl)cyclopentyl]hexa-3''E,5''E-dienyl ester

(1'R,2S,2'R,8R,9S,11R,13S,15S,16S)-9,16-bis(tert-butyldimethylsilyloxy)-2-[2'-(4''-methoxybenzyloxymethyl)cyclopentyl]-9,11,13,15-tetramethyl-18-oxo-oxaoctadeca-4E,6Z-diene-7-carbonitrile

(1'S,1''R,2''R,3S,4S,6S,8R,10S)-3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoic acid 6''-bromo-6''-cyano-1-[2'''-(4'''-methoxymenzyloxymethyl)cyclopentyl]hexa-3''E,5''E-dienyl ester

(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-16-(tert-butyldimethylsilyloxy)-8-hydroxy-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carbonitrile