(4aR,6S,7R,8aS)-4-(4-methoxybenzyloxy)butyric acid 2,2-di(tert-butyl)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-yl ester

Base Information

Chemical Name:(4aR,6S,7R,8aS)-4-(4-methoxybenzyloxy)butyric acid 2,2-di(tert-butyl)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-yl ester
CAS No.:511256-85-2
Molecular Formula:C₃₁H₅₀O₇Si
Molecular Weight:562.819
Hs Code.:

(4aR,6S,7R,8aS)-4-(4-methoxybenzyloxy)butyric acid 2,2-di(tert-butyl)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-yl ester

Synonyms:(4aR,6S,7R,8aS)-4-(4-methoxybenzyloxy)butyric acid 2,2-di(tert-butyl)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-yl ester

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Chemical Property of (4aR,6S,7R,8aS)-4-(4-methoxybenzyloxy)butyric acid 2,2-di(tert-butyl)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-yl ester

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Technology Process of (4aR,6S,7R,8aS)-4-(4-methoxybenzyloxy)butyric acid 2,2-di(tert-butyl)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-yl ester

There total 10 articles about (4aR,6S,7R,8aS)-4-(4-methoxybenzyloxy)butyric acid 2,2-di(tert-butyl)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-yl ester 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:

: (4aR,6S,7R,8aS)-4-(4-methoxybenzyloxy)butyric acid 2,2-di(tert-butyl)-6-methyl-6-(2-methylallyl)-8-(methylsulfanylthiocarbonyloxy)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-yl ester

: 511256-85-2
(4aR,6S,7R,8aS)-4-(4-methoxybenzyloxy)butyric acid 2,2-di(tert-butyl)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-yl ester

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 110 ℃; for 2h;
DOI:10.1021/ol034100w

Reference yield:

: 191593-14-3
4,6-O-di(tert-butyl)silanediyl-D-glucal

: 511256-85-2
(4aR,6S,7R,8aS)-4-(4-methoxybenzyloxy)butyric acid 2,2-di(tert-butyl)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 97 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / 0 °C

2.2: 95 percent / tetrahydrofuran; pentane / -70 - 20 °C

3.1: dimethyl dioxirane / CH₂Cl₂ / 0.5 h / -65 °C

3.2: 90 percent / CH₂Cl₂ / 0.25 h / -65 °C

4.1: 95 percent / NaH / hexamethylphosphoric acid triamide / 0.5 h / 0 °C

5.1: 86 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h / -65 - 20 °C

6.1: 93 percent / DCC; DMAP / CH₂Cl₂ / 14 h / 20 °C

7.1: 100 percent / glacial AcOH / methanol; H₂O / 6 h / 0 °C

8.1: NaH / 4 h / 20 °C

8.2: 86 percent / 48 h / 20 °C

9.1: 19.4 mg / n-Bu₃SnH; AIBN / toluene / 2 h / 110 °C

With 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); tert.-butyl lithium; tri-n-butyl-tin hydride; 3,3-dimethyldioxirane; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; N,N-dimethyl-formamide; toluene; pentane;
DOI:10.1021/ol034100w

Reference yield:

: 511256-93-2
(4aR,6S,7R,8S,8aR)-2,2-di(tert-butyl)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalene-7,8-diol

: 511256-85-2
(4aR,6S,7R,8aS)-4-(4-methoxybenzyloxy)butyric acid 2,2-di(tert-butyl)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 86 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h / -65 - 20 °C

2.1: 93 percent / DCC; DMAP / CH₂Cl₂ / 14 h / 20 °C

3.1: 100 percent / glacial AcOH / methanol; H₂O / 6 h / 0 °C

4.1: NaH / 4 h / 20 °C

4.2: 86 percent / 48 h / 20 °C

5.1: 19.4 mg / n-Bu₃SnH; AIBN / toluene / 2 h / 110 °C

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; water; toluene;
DOI:10.1021/ol034100w