Benzoic acid (1R,7S,19R)-21-(tert-butyl-diphenyl-silanyloxy)-7,19-dihydroxy-1-methyl-henicosyl ester

Base Information

Chemical Name:Benzoic acid (1R,7S,19R)-21-(tert-butyl-diphenyl-silanyloxy)-7,19-dihydroxy-1-methyl-henicosyl ester
CAS No.:532929-62-7
Molecular Formula:C₄₅H₆₈O₅Si
Molecular Weight:717.117
Hs Code.:

Synonyms:Benzoic acid (1R,7S,19R)-21-(tert-butyl-diphenyl-silanyloxy)-7,19-dihydroxy-1-methyl-henicosyl ester

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Chemical Property of Benzoic acid (1R,7S,19R)-21-(tert-butyl-diphenyl-silanyloxy)-7,19-dihydroxy-1-methyl-henicosyl ester

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Technology Process of Benzoic acid (1R,7S,19R)-21-(tert-butyl-diphenyl-silanyloxy)-7,19-dihydroxy-1-methyl-henicosyl ester

There total 22 articles about Benzoic acid (1R,7S,19R)-21-(tert-butyl-diphenyl-silanyloxy)-7,19-dihydroxy-1-methyl-henicosyl 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: 30.0%

: 98-88-4
benzoyl chloride

: 532929-61-6
(2R,8S,20R)-22-(tert-Butyl-diphenyl-silanyloxy)-docosane-2,8,20-triol

: 532929-62-7
Benzoic acid (1R,7S,19R)-21-(tert-butyl-diphenyl-silanyloxy)-7,19-dihydroxy-1-methyl-henicosyl ester

Guidance literature:: With pyridine; In dichloromethane; at -30 ℃;
DOI:10.1021/ol034338k

Reference yield:

: 112-45-8
10-Undecenal

: 532929-62-7
Benzoic acid (1R,7S,19R)-21-(tert-butyl-diphenyl-silanyloxy)-7,19-dihydroxy-1-methyl-henicosyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: NaH / tetrahydrofuran / 0 °C

2.1: i-Bu₂AlH / CH₂Cl₂ / -78 °C

3.1: 82 percent / (-)-diethyl tartrate; titanium(IV) isopropoxide; t-butyl hydroperoxide / molecular sieves 4 Angstroem / CH₂Cl₂ / -23 °C

4.1: Red-Al / tetrahydrofuran / 0 - 20 °C

4.2: 76 percent / NaIO₄ / CH₂Cl₂; acetone; H₂O

5.1: 99 percent / imidazole / dimethylformamide / 0 °C

6.1: 99 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 20 °C

7.1: BH₃*SMe₂ / tetrahydrofuran / 0 °C

7.2: 87 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0 - 20 °C

8.1: 92 percent / I₂; triphenylphosphine; imidazole / benzene / 10 °C

9.1: t-BuLi / hexane; diethyl ether / -78 - 20 °C

9.2: CuI / hexane; diethyl ether

9.3: 78 percent / hexane; diethyl ether / -78 °C

10.1: 85 percent / pyridinium p-toluenesulfonate / ethanol / 50 °C

11.1: 30 percent / pyridine / CH₂Cl₂ / -30 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dimethylsulfide borane complex; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; (-)-diethyl tartrate; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; 4 A molecular sieve; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: Wittig reaction / 3.1: Sharpless epoxidation;
DOI:10.1021/ol034338k

Reference yield:

: 103367-38-0
methyl 5(R)-(tetrahydropyranyloxy)-hexanoate

: 532929-62-7
Benzoic acid (1R,7S,19R)-21-(tert-butyl-diphenyl-silanyloxy)-7,19-dihydroxy-1-methyl-henicosyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: LiAlH₄ / tetrahydrofuran / 0 °C

2.1: pyridine / 0 °C

3.1: dimethylsulfoxide / 20 °C

4.1: i-Bu₂AlH / CH₂Cl₂ / -78 °C

5.1: 99 percent / NaH / tetrahydrofuran / 0 °C

6.1: i-Bu₂AlH / CH₂Cl₂ / -78 °C

7.1: 89 percent / (+)-diethyl tartrate; titanium(IV) isopropoxide; t-butyl hydroperoxide / molecular sieves 4 Angstroem / CH₂Cl₂ / -23 °C

8.1: 80 percent / i-Bu₂AlH / CH₂Cl₂ / 0 °C

9.1: 82 percent / Bu₂SnO; triethylamine / CH₂Cl₂ / 20 °C

10.1: 97 percent / K₂CO₃ / methanol / 20 °C

11.1: t-BuLi / hexane; diethyl ether / -78 - 20 °C

11.2: CuI / hexane; diethyl ether

11.3: 78 percent / hexane; diethyl ether / -78 °C

12.1: 85 percent / pyridinium p-toluenesulfonate / ethanol / 50 °C

13.1: 30 percent / pyridine / CH₂Cl₂ / -30 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; (+)-Weinsaeure-diethylester; triethylamine; 4 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; 5.1: Wittig reaction / 7.1: Sharpless epoxidation;
DOI:10.1021/ol034338k