benzoic acid {6-[3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl}-(2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester

Base Information

• Chemical Name: benzoic acid {6-[3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl}-(2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester
• CAS No.: 302355-96-0
• Molecular Formula: C₄₄H₆₇NO₁₁SeSi
• Molecular Weight: 893.062

Synonyms:

Chemical Property of benzoic acid {6-[3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl}-(2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzoic acid {6-[3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl}-(2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester

There total 8 articles about benzoic acid {6-[3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl}-(2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-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:

benzoyl chloride (98-88-4) + C37H63NO10SeSi → benzoic acid {6-[3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl}-(2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester (302355-96-0) + benzoic acid {6-[3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl}-(2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester

Guidance literature:

With dmap; 4 A molecular sieve; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1039/a909898d

Reference yield:

diphenyl diselenide (1666-13-3) → benzoic acid {6-[3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl}-(2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester (302355-96-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaBH₄ / ethanol

1.2: 80 percent / ethanol / 10 h / Heating

2.1: n-BuLi; DIBALH / hexane; CH₂Cl₂; tetrahydrofuran / 3.08 h / -78 - -20 °C

2.2: 72 percent / aq. HCl / diethyl ether; tetrahydrofuran; CH₂Cl₂ / 24 h

3.1: 44 mg

4.1: LiBH(s-Bu)3 / tetrahydrofuran / 0.17 h / -95 °C

5.1: CSA / CH₂Cl₂ / 1.5 h / 20 °C

6.1: DMAP; DIPEA; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

With dmap; sodium tetrahydroborate; n-butyllithium; 4 A molecular sieve; camphor-10-sulfonic acid; L-Selectride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; 1.1: Metallation / 1.2: Ring cleavage / 2.1: Reduction / 2.2: Cyclization / 4.1: Reduction / 5.1: Addition / 6.1: Acylation;

DOI:10.1039/a909898d

Reference yield:

(4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-one (139403-50-2) → benzoic acid {6-[3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl}-(2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester (302355-96-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 44 mg

2: LiBH(s-Bu)3 / tetrahydrofuran / 0.17 h / -95 °C

3: CSA / CH₂Cl₂ / 1.5 h / 20 °C

4: DMAP; DIPEA; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

With dmap; 4 A molecular sieve; camphor-10-sulfonic acid; L-Selectride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 2: Reduction / 3: Addition / 4: Acylation;

DOI:10.1039/a909898d

upstream raw materials:

benzoyl chloride

diphenyl diselenide

(4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-one

(R)-4-[(1R,2R)-2-(4-Chlorobenzoyloxy)-1-methylpropyl]dihydrofuran-2(2H)-one

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