(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

Base Information

Chemical Name:(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
CAS No.:251641-57-3
Molecular Formula:C₃₆H₆₆O₇Si₂
Molecular Weight:667.087
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 19 articles about (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 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: 87.0%

: 824-94-2
p-methoxybenzyl chloride

: 251641-56-2
(2R,4S,6S,8R,10S)-8-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-10-methoxy-2-triisopropylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undecan-4-ol

: 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

Guidance literature:: (2R,4S,6S,8R,10S)-8-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-10-methoxy-2-triisopropylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undecan-4-ol; With potassium hexamethylsilazane; In tetrahydrofuran;

p-methoxybenzyl chloride;
DOI:10.1021/jo9910987

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 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

Guidance literature:: Multi-step reaction with 12 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

With 1H-imidazole; 2,6-di-tert-butyl-4-methylpyridine; 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; 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;
DOI:10.1021/jo9910987

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 11 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

With sodium tetrahydroborate; 2,6-di-tert-butyl-4-methylpyridine; 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; 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;
DOI:10.1021/jo9910987