(-)-(S)-[(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-(2-hydroxymethylcyclohex-1-enyl)methanol

Base Information

Chemical Name:(-)-(S)-[(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-(2-hydroxymethylcyclohex-1-enyl)methanol
CAS No.:470690-27-8
Molecular Formula:C₃₃H₄₆O₅Si
Molecular Weight:550.811
Hs Code.:

(-)-(S)-[(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-(2-hydroxymethylcyclohex-1-enyl)methanol

Synonyms:(-)-(S)-[(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-(2-hydroxymethylcyclohex-1-enyl)methanol

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Chemical Property of (-)-(S)-[(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-(2-hydroxymethylcyclohex-1-enyl)methanol

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Technology Process of (-)-(S)-[(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-(2-hydroxymethylcyclohex-1-enyl)methanol

There total 19 articles about (-)-(S)-[(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-(2-hydroxymethylcyclohex-1-enyl)methanol 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: 61.0%

: 470690-24-5
(+)-(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-1-[(1S)-3-oxo-1,3,4,5,6,7-hexahydroisobenzofuran-1-yl]-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

: 470690-27-8
(-)-(S)-[(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-(2-hydroxymethylcyclohex-1-enyl)methanol

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃; for 0.25h;
DOI:10.1039/b201987f

Reference yield:

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

: 470690-27-8
(-)-(S)-[(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-(2-hydroxymethylcyclohex-1-enyl)methanol

Guidance literature:: Multi-step reaction with 15 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

14.1: 69 percent / CrCl₂ / NiCl₂ / dimethylformamide / 16 h / 50 °C

15.1: 61 percent / LiAlH₄ / diethyl ether / 0.25 h / 20 °C

With pyridine; 1H-imidazole; chromium dichloride; hydrogenchloride; potassium hydroxide; lithium aluminium tetrahydride; 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; nickel dichloride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone; acetonitrile; 3.2: intramolecular Diels-Alder reaction;
DOI:10.1039/b201987f

Reference yield:

: 98-01-1
furfural

: 470690-27-8
(-)-(S)-[(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-(2-hydroxymethylcyclohex-1-enyl)methanol

Guidance literature:: Multi-step reaction with 18 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

17.1: 69 percent / CrCl₂ / NiCl₂ / dimethylformamide / 16 h / 50 °C

18.1: 61 percent / LiAlH₄ / diethyl ether / 0.25 h / 20 °C

With pyridine; 1H-imidazole; chromium dichloride; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; 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; nickel dichloride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; acetonitrile; 6.2: intramolecular Diels-Alder reaction;
DOI:10.1039/b201987f