3-(tert-butyldiphenylsilanyloxy)-4-[6-(2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-tetrahydropyran-2-yl]-butyric acid

Base Information

Chemical Name:3-(tert-butyldiphenylsilanyloxy)-4-[6-(2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-tetrahydropyran-2-yl]-butyric acid
CAS No.:500208-41-3
Molecular Formula:C₃₂H₄₆O₆Si
Molecular Weight:554.799
Hs Code.:

Synonyms:3-(tert-butyldiphenylsilanyloxy)-4-[6-(2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-tetrahydropyran-2-yl]-butyric acid

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Chemical Property of 3-(tert-butyldiphenylsilanyloxy)-4-[6-(2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-tetrahydropyran-2-yl]-butyric acid

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Technology Process of 3-(tert-butyldiphenylsilanyloxy)-4-[6-(2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-tetrahydropyran-2-yl]-butyric acid

There total 6 articles about 3-(tert-butyldiphenylsilanyloxy)-4-[6-(2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-tetrahydropyran-2-yl]-butyric acid 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: 92.0%

: 500208-48-0
3-(tert-butyldiphenylsilanyloxy)-4-[6-(2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-tetrahydropyran-2-yl]-butan-1-ol

: 500208-41-3
3-(tert-butyldiphenylsilanyloxy)-4-[6-(2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-tetrahydropyran-2-yl]-butyric acid

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; In phosphate buffer; water; acetonitrile; at 45 ℃; for 4h; pH=7;
DOI:10.1021/ol0272390

Reference yield:

: 500208-43-5
6-[4-benzyloxy-2-(tert-butyldiphenylsilanyloxy)-butyl]-tetrahydropyran-2-one

: 500208-41-3
3-(tert-butyldiphenylsilanyloxy)-4-[6-(2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-tetrahydropyran-2-yl]-butyric acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

1.2: tetrahydrofuran; hexane / 1 h / -78 °C

2.1: 278 g / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 4 h / -30 °C

3.1: 91 percent / hydrogen / Ru-R-(BINAP)Cl₂ / ethanol / 96 h / 20 °C / 58505.9 Torr

4.1: hydrogen / Pd(OH)2 / diethyl ether / 1 h / 760.05 Torr

4.2: 96 percent / lithium borohydride / diethyl ether / 1 h

5.1: 93 percent / PPTS / dimethylformamide / 3 h / 20 °C

6.1: 92 percent / TEMPO; NaClO₂; NaOCl / acetonitrile; H₂O; aq. phosphate buffer / 4 h / 45 °C / pH 7

With triethylsilane; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; n-butyllithium; hydrogen; pyridinium p-toluenesulfonate; diisopropylamine; trifluoroacetic acid; palladium dihydroxide; RuCl₂[(R)-BINAP]; In tetrahydrofuran; phosphate buffer; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 3.1: Noyori asymmetric hydrogenation;
DOI:10.1021/ol0272390

Reference yield:

: 500208-47-9
4-{6-[4-benzyloxy-2-(tert-butyldiphenylsilanyloxy)-butyl]-tetrahydropyran-2-yl}-3-oxobutyric acid ethyl ester

: 500208-41-3
3-(tert-butyldiphenylsilanyloxy)-4-[6-(2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-tetrahydropyran-2-yl]-butyric acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: 91 percent / hydrogen / Ru-R-(BINAP)Cl₂ / ethanol / 96 h / 20 °C / 58505.9 Torr

2.1: hydrogen / Pd(OH)2 / diethyl ether / 1 h / 760.05 Torr

2.2: 96 percent / lithium borohydride / diethyl ether / 1 h

3.1: 93 percent / PPTS / dimethylformamide / 3 h / 20 °C

4.1: 92 percent / TEMPO; NaClO₂; NaOCl / acetonitrile; H₂O; aq. phosphate buffer / 4 h / 45 °C / pH 7

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; hydrogen; pyridinium p-toluenesulfonate; palladium dihydroxide; RuCl₂[(R)-BINAP]; In phosphate buffer; diethyl ether; ethanol; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Noyori asymmetric hydrogenation;
DOI:10.1021/ol0272390