2-[(2R,4S,6S,8R,9S)-4-Benzyloxy-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-ethanol

Base Information

Chemical Name:2-[(2R,4S,6S,8R,9S)-4-Benzyloxy-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-ethanol
CAS No.:87319-11-7
Molecular Formula:C₂₃H₃₄O₄
Molecular Weight:374.521
Hs Code.:

Synonyms:2-[(2R,4S,6S,8R,9S)-4-Benzyloxy-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-ethanol

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Chemical Property of 2-[(2R,4S,6S,8R,9S)-4-Benzyloxy-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-ethanol

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Technology Process of 2-[(2R,4S,6S,8R,9S)-4-Benzyloxy-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-ethanol

There total 25 articles about 2-[(2R,4S,6S,8R,9S)-4-Benzyloxy-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-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: 87.0%

: 87319-10-6
{2-[(2R,4S,6S,8R,9S)-4-Benzyloxy-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-ethoxy}-tert-butyl-diphenyl-silane

: 87319-11-7
2-[(2R,4S,6S,8R,9S)-4-Benzyloxy-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-ethanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1021/ja00270a059

Reference yield:

: 87319-06-0
(3S,4R,5S)-3,5-Dimethyl-hept-1-yn-4-ol

: 87319-11-7
2-[(2R,4S,6S,8R,9S)-4-Benzyloxy-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-ethanol

Guidance literature:: Multi-step reaction with 3 steps

1: Et₃N, DMAP / CH₂Cl₂

2: 1.) n-BuLi, PPTS; 2.) H₂, pyridine; 3.) BF₃*Et₂O / 2.) Pd/BaSO₄-C / 1.) Et₂O, -78 deg C; 2.) EtOAc; 3.) THF

3: 87 percent / n-Bu₄NF / tetrahydrofuran

With pyridine; dmap; n-butyllithium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; triethylamine; Pd-BaSO₄; pyrographite; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00270a059

Reference yield:

: 87319-05-9
(3S,4R,5S)-4-Methoxymethoxy-3,5-dimethyl-hept-1-yne

: 87319-11-7
2-[(2R,4S,6S,8R,9S)-4-Benzyloxy-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-ethanol

Guidance literature:: Multi-step reaction with 4 steps

1: Me₃SiBr / CH₂Cl₂ / -30 °C

2: Et₃N, DMAP / CH₂Cl₂

3: 1.) n-BuLi, PPTS; 2.) H₂, pyridine; 3.) BF₃*Et₂O / 2.) Pd/BaSO₄-C / 1.) Et₂O, -78 deg C; 2.) EtOAc; 3.) THF

4: 87 percent / n-Bu₄NF / tetrahydrofuran

With pyridine; dmap; n-butyllithium; trimethylsilyl bromide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; triethylamine; Pd-BaSO₄; pyrographite; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00270a059