(R)-2-Benzyloxy-2-[(2R,4aR,6R,7S,8R,8aR)-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

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Chemical Name:(R)-2-Benzyloxy-2-[(2R,4aR,6R,7S,8R,8aR)-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol
CAS No.:251319-63-8
Molecular Formula:C₂₉H₄₂O₆Si
Molecular Weight:514.734
Hs Code.:

Synonyms:(R)-2-Benzyloxy-2-[(2R,4aR,6R,7S,8R,8aR)-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

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Chemical Property of (R)-2-Benzyloxy-2-[(2R,4aR,6R,7S,8R,8aR)-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

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Technology Process of (R)-2-Benzyloxy-2-[(2R,4aR,6R,7S,8R,8aR)-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

There total 14 articles about (R)-2-Benzyloxy-2-[(2R,4aR,6R,7S,8R,8aR)-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol 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: 88.0%

: 251319-68-3
(2R,4aR,6R,7S,8R,8aR)-6-[(R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 251319-63-8
(R)-2-Benzyloxy-2-[(2R,4aR,6R,7S,8R,8aR)-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

Guidance literature:: With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/S0040-4039(99)01481-1

Reference yield:

: 251319-56-9
(2R,3R,4E)-2-methyl-3-(tert-butyldimethylsilyloxy)-6-(phenylmethoxy)hex-4-en-1-al

: 251319-63-8
(R)-2-Benzyloxy-2-[(2R,4aR,6R,7S,8R,8aR)-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

Guidance literature:: Multi-step reaction with 13 steps

1.1: potassium hexamethyldisilazide; 18-crown-6 / tetrahydrofuran / -78 °C

1.2: diisobutyl aluminium hydride / CH₂Cl₂ / -78 °C

2.1: imidazole / dimethylformamide / 20 °C

3.1: 97 percent / di-tert-butyldiphenyllithium / tetrahydrofuran / -78 °C

4.1: 82 percent / (-)-diethyl tartrate; 4 Angstroem molecular sieves; tBuOOH / Ti(iPrO)4 / CH₂Cl₂ / -20 °C

5.1: 80 percent / Ti(iPrO)4 / tetrahydrofuran / 20 °C

6.1: 99 percent / Et₃N / CH₂Cl₂ / 20 °C

7.1: 99 percent / dimethyl dioxirane / CH₂Cl₂ / -20 °C

8.1: camphorsulfonic acid / CH₂Cl₂; methanol / -20 °C

9.1: 83 percent / camphorsulfonic acid / CH₂Cl₂ / 20 °C

10.1: 76 percent / diisobutyl aluminium hydride / CH₂Cl₂ / -78 °C

11.1: 80 percent / camphorsulfonic acid / CH₂Cl₂ / 20 °C

12.1: 98 percent / KH / tetrahydrofuran / 0 °C

13.1: 88 percent / HF*Py; pyridine / tetrahydrofuran / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; 4 A molecular sieve; camphor-10-sulfonic acid; 3,3-dimethyldioxirane; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; lithium 4,4′-di-tert-butylbiphenylide; pyridine hydrogenfluoride; (-)-diethyl tartrate; triethylamine; titanium(IV) isopropylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Alkylation / 1.2: Reduction / 2.1: silylation / 3.1: Hydrolysis / 4.1: Epoxidation / 5.1: benzoylation / 6.1: silylation / 7.1: Epoxidation / 8.1: Hydrolysis / 9.1: Cyclization / 10.1: Hydrogenolysis / 11.1: Condensation / 12.1: benzylation / 13.1: Hydrolysis;
DOI:10.1016/S0040-4039(99)01481-1

Reference yield:

: 321921-91-9
(2Z,6E)-(4S,5S)-8-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-octa-2,6-dien-1-ol

: 251319-63-8
(R)-2-Benzyloxy-2-[(2R,4aR,6R,7S,8R,8aR)-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

Guidance literature:: Multi-step reaction with 12 steps

1: imidazole / dimethylformamide / 20 °C

2: 97 percent / di-tert-butyldiphenyllithium / tetrahydrofuran / -78 °C

3: 82 percent / (-)-diethyl tartrate; 4 Angstroem molecular sieves; tBuOOH / Ti(iPrO)4 / CH₂Cl₂ / -20 °C

4: 80 percent / Ti(iPrO)4 / tetrahydrofuran / 20 °C

5: 99 percent / Et₃N / CH₂Cl₂ / 20 °C

6: 99 percent / dimethyl dioxirane / CH₂Cl₂ / -20 °C

7: camphorsulfonic acid / CH₂Cl₂; methanol / -20 °C

8: 83 percent / camphorsulfonic acid / CH₂Cl₂ / 20 °C

9: 76 percent / diisobutyl aluminium hydride / CH₂Cl₂ / -78 °C

10: 80 percent / camphorsulfonic acid / CH₂Cl₂ / 20 °C

11: 98 percent / KH / tetrahydrofuran / 0 °C

12: 88 percent / HF*Py; pyridine / tetrahydrofuran / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 4 A molecular sieve; camphor-10-sulfonic acid; 3,3-dimethyldioxirane; potassium hydride; diisobutylaluminium hydride; lithium 4,4′-di-tert-butylbiphenylide; pyridine hydrogenfluoride; (-)-diethyl tartrate; triethylamine; titanium(IV) isopropylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: silylation / 2: Hydrolysis / 3: Epoxidation / 4: benzoylation / 5: silylation / 6: Epoxidation / 7: Hydrolysis / 8: Cyclization / 9: Hydrogenolysis / 10: Condensation / 11: benzylation / 12: Hydrolysis;
DOI:10.1016/S0040-4039(99)01481-1