(+)-(1R,2S,4R,5S)-1-(tert-butyldiphenylsilyloxy)-1-formyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

Base Information

Chemical Name:(+)-(1R,2S,4R,5S)-1-(tert-butyldiphenylsilyloxy)-1-formyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester
CAS No.:470690-17-6
Molecular Formula:C₂₈H₃₆O₅Si
Molecular Weight:480.676
Hs Code.:

Synonyms:(+)-(1R,2S,4R,5S)-1-(tert-butyldiphenylsilyloxy)-1-formyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

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Chemical Property of (+)-(1R,2S,4R,5S)-1-(tert-butyldiphenylsilyloxy)-1-formyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

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Technology Process of (+)-(1R,2S,4R,5S)-1-(tert-butyldiphenylsilyloxy)-1-formyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

There total 17 articles about (+)-(1R,2S,4R,5S)-1-(tert-butyldiphenylsilyloxy)-1-formyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl 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: 87.0%

: 470690-23-4
(+)-(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-1-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

: 470690-17-6
(+)-(1R,2S,4R,5S)-1-(tert-butyldiphenylsilyloxy)-1-formyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

Guidance literature:: With N-methyl-2-indolinone; tetrapropylammonium perruthennate; In acetone; for 1.5h;
DOI:10.1039/b201987f

Reference yield:

: 3350-78-5
3,3-Dimethylacryloyl chloride

: 470690-17-6
(+)-(1R,2S,4R,5S)-1-(tert-butyldiphenylsilyloxy)-1-formyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: pyridine / tetrahydrofuran / 16 h

2.1: 139 g / aq. HCl / tetrahydrofuran

3.1: n-BuMgCl / diethyl ether / 0.75 h / -60 °C

3.2: 69 percent / toluene / 16 h / Heating

4.1: TsCl; pyridine / 19 h / 20 - 50 °C

5.1: DBU / acetonitrile / 16 h / 20 °C

6.1: 33.8 g / aq. HCl / CH₂Cl₂ / 0.5 h

7.1: NaNO₂; Ac₂O / acetic acid / 0.5 h / 20 °C

8.1: 7.2 g / KOH / 0.33 h / -20 °C

9.1: 91 percent / imidazole / CH₂Cl₂ / 16 h

10.1: disiamylborane / tetrahydrofuran / 3 h / 0 °C

10.2: 76 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 2 h / 20 °C

11.1: 92 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

12.1: 86 percent / aq. HCl / ethanol

13.1: 87 percent / NMO / TPAP / acetone / 1.5 h

With pyridine; 1H-imidazole; hydrogenchloride; potassium hydroxide; N-methyl-2-indolinone; butyl magnesium bromide; bis-(1,2-dimethylpropyl)borane; acetic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; p-toluenesulfonyl chloride; sodium nitrite; tetrapropylammonium perruthennate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; acetic acid; acetone; acetonitrile; 3.2: intramolecular Diels-Alder reaction;
DOI:10.1039/b201987f

Reference yield:

: 98-01-1
furfural

: 470690-17-6
(+)-(1R,2S,4R,5S)-1-(tert-butyldiphenylsilyloxy)-1-formyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: toluene / 2 h / Heating

2.1: 121 g / NaBH₄ / propan-2-ol / 16 h / 20 °C

3.1: pyridine / tetrahydrofuran / 2 h

4.1: pyridine / tetrahydrofuran / 16 h

5.1: 139 g / aq. HCl / tetrahydrofuran

6.1: n-BuMgCl / diethyl ether / 0.75 h / -60 °C

6.2: 69 percent / toluene / 16 h / Heating

7.1: TsCl; pyridine / 19 h / 20 - 50 °C

8.1: DBU / acetonitrile / 16 h / 20 °C

9.1: 33.8 g / aq. HCl / CH₂Cl₂ / 0.5 h

10.1: NaNO₂; Ac₂O / acetic acid / 0.5 h / 20 °C

11.1: 7.2 g / KOH / 0.33 h / -20 °C

12.1: 91 percent / imidazole / CH₂Cl₂ / 16 h

13.1: disiamylborane / tetrahydrofuran / 3 h / 0 °C

13.2: 76 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 2 h / 20 °C

14.1: 92 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

15.1: 86 percent / aq. HCl / ethanol

16.1: 87 percent / NMO / TPAP / acetone / 1.5 h

With pyridine; 1H-imidazole; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; N-methyl-2-indolinone; butyl magnesium bromide; bis-(1,2-dimethylpropyl)borane; acetic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; p-toluenesulfonyl chloride; sodium nitrite; tetrapropylammonium perruthennate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; acetic acid; isopropyl alcohol; acetone; toluene; acetonitrile; 6.2: intramolecular Diels-Alder reaction;
DOI:10.1039/b201987f