2-[(2R,4S,6R,8R,10S)-4-Methoxy-10-(4-methoxy-benzyloxy)-8-triisopropylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol

Base Information

Chemical Name:2-[(2R,4S,6R,8R,10S)-4-Methoxy-10-(4-methoxy-benzyloxy)-8-triisopropylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol
CAS No.:251641-58-4
Molecular Formula:C₃₀H₅₂O₇Si
Molecular Weight:552.824
Hs Code.:

Synonyms:2-[(2R,4S,6R,8R,10S)-4-Methoxy-10-(4-methoxy-benzyloxy)-8-triisopropylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol

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Chemical Property of 2-[(2R,4S,6R,8R,10S)-4-Methoxy-10-(4-methoxy-benzyloxy)-8-triisopropylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol

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Technology Process of 2-[(2R,4S,6R,8R,10S)-4-Methoxy-10-(4-methoxy-benzyloxy)-8-triisopropylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol

There total 20 articles about 2-[(2R,4S,6R,8R,10S)-4-Methoxy-10-(4-methoxy-benzyloxy)-8-triisopropylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-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: 86.0%

: 251641-57-3
(2R,4S,6R,8R,10S)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-10-(4-methoxy-benzyloxy)-8-triisopropylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undecane

: 251641-58-4
2-[(2R,4S,6R,8R,10S)-4-Methoxy-10-(4-methoxy-benzyloxy)-8-triisopropylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol

Guidance literature:: With fluorosilicic acid; In acetonitrile; tert-butyl alcohol; at 0 ℃;
DOI:10.1021/jo9910987

Reference yield:

: 112348-03-5
(R)-3-Hydroxy-4-triisopropylsilanyloxy-butyric acid ethyl ester

: 251641-58-4
2-[(2R,4S,6R,8R,10S)-4-Methoxy-10-(4-methoxy-benzyloxy)-8-triisopropylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol

Guidance literature:: Multi-step reaction with 12 steps

1.1: LDA / tetrahydrofuran / -78 °C

1.2: 84 percent / tetrahydrofuran / -78 - 20 °C

2.1: Et₂BOMe; NaBH₄ / methanol; tetrahydrofuran

3.1: pyridinium p-toluenesulfonate / CH₂Cl₂ / Heating

4.1: 88 percent / diisobutylaluminium hydride / toluene

5.1: 80 percent / LDA / tetrahydrofuran

6.1: 87 percent / Dess-Martin periodinane

7.1: H₂ / Pd(OH)2/C / ethyl acetate

8.1: ZnBr₂ / CH₂Cl₂ / -78 - 0 °C

9.1: 74 percent / K; NH₃ / diethyl ether; methanol

10.1: 84 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 0 °C

11.1: 87 percent / KHMDS / tetrahydrofuran

12.1: 86 percent / H₂SiF₆ / 2-methyl-propan-2-ol; acetonitrile / 0 °C

With sodium tetrahydroborate; 2,6-di-tert-butyl-4-methylpyridine; fluorosilicic acid; diethyl methoxy borane; ammonia; hydrogen; potassium; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; zinc dibromide; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; toluene; acetonitrile; tert-butyl alcohol; 1.1: Metallation / 1.2: Condensation / 2.1: Reduction / 3.1: Cyclization / 4.1: Reduction / 5.1: Metallation / 5.2: Condensation / 6.1: Oxidation / 7.1: Hydrogenation / 8.1: Cyclization / 9.1: Reduction / 10.1: Methylation / 11.1: Metallation / 11.2: Alkylation / 12.1: desilylation;
DOI:10.1021/jo9910987

Reference yield:

: (R)-3,5-Dihydroxy-pentanoic acid ethyl ester

: 251641-58-4
2-[(2R,4S,6R,8R,10S)-4-Methoxy-10-(4-methoxy-benzyloxy)-8-triisopropylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol

Guidance literature:: Multi-step reaction with 13 steps

1: imidazole / tetrahydrofuran / 0 °C

2: BF₃*OEt₂ / CH₂Cl₂

3: 85 percent / diisobutylaluminium hydride / CH₂Cl₂

4: diethyl ether / 0 °C

5: Dess-Martin periodinane

6: 80 percent / LDA / tetrahydrofuran

7: 87 percent / Dess-Martin periodinane

8: H₂ / Pd(OH)2/C / ethyl acetate

9: ZnBr₂ / CH₂Cl₂ / -78 - 0 °C

10: 74 percent / K; NH₃ / diethyl ether; methanol

11: 84 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 0 °C

12: 87 percent / KHMDS / tetrahydrofuran

13: 86 percent / H₂SiF₆ / 2-methyl-propan-2-ol; acetonitrile / 0 °C

With 1H-imidazole; 2,6-di-tert-butyl-4-methylpyridine; fluorosilicic acid; boron trifluoride diethyl etherate; ammonia; hydrogen; potassium; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; zinc dibromide; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; acetonitrile; tert-butyl alcohol; 1: silylation / 2: Alkylation / 3: Reduction / 4: Grignard reaction / 5: Oxidation / 6: Metallation / 6: Condensation / 7: Oxidation / 8: Hydrogenation / 9: Cyclization / 10: Reduction / 11: Methylation / 12: Metallation / 12: Alkylation / 13: desilylation;
DOI:10.1021/jo9910987