(1S,2S,3S,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-methyl-7-oxabicyclo[2.2.1]hept-5-ene

Base Information

Chemical Name:(1S,2S,3S,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-methyl-7-oxabicyclo[2.2.1]hept-5-ene
CAS No.:817201-20-0
Molecular Formula:C₂₄H₃₀O₂Si
Molecular Weight:378.587
Hs Code.:

Synonyms:(1S,2S,3S,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-methyl-7-oxabicyclo[2.2.1]hept-5-ene

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Chemical Property of (1S,2S,3S,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-methyl-7-oxabicyclo[2.2.1]hept-5-ene

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Technology Process of (1S,2S,3S,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-methyl-7-oxabicyclo[2.2.1]hept-5-ene

There total 11 articles about (1S,2S,3S,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-methyl-7-oxabicyclo[2.2.1]hept-5-ene 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:

: 6118-51-0
exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

: 817201-20-0
(1S,2S,3S,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-methyl-7-oxabicyclo[2.2.1]hept-5-ene

Guidance literature:: Multi-step reaction with 7 steps

1: LiAlH₄ / tetrahydrofuran / 20 h / 0 °C

2: 2.92 g / pyridine / 17 h / 20 °C

3: lipase PS (Amano); H₂O / tetrahydrofuran / 480 h / 20 °C

4: imidazole / dimethylformamide / 23 h / 0 °C

5: 1.90 g / NaOMe / methanol / 2 h / 20 °C

6: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 22 h / 0 °C

7: 110 mg / NaBH₄; DMPU / 2 h / 90 °C

With pyridine; 1H-imidazole; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; lithium aluminium tetrahydride; Lipase PS (Amano); water; sodium methylate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo048566j

Reference yield:

: 106137-27-3,817201-06-2
exo-2,3-bis(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-5-ene

: 817201-20-0
(1S,2S,3S,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-methyl-7-oxabicyclo[2.2.1]hept-5-ene

Guidance literature:: Multi-step reaction with 6 steps

1: 2.92 g / pyridine / 17 h / 20 °C

2: lipase PS (Amano); H₂O / tetrahydrofuran / 480 h / 20 °C

3: imidazole / dimethylformamide / 23 h / 0 °C

4: 1.90 g / NaOMe / methanol / 2 h / 20 °C

5: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 22 h / 0 °C

6: 110 mg / NaBH₄; DMPU / 2 h / 90 °C

With pyridine; 1H-imidazole; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; Lipase PS (Amano); water; sodium methylate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo048566j

Reference yield:

: 142438-51-5
(1R*,2R*,3S*,4S*)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-diylbis(methylene) diacetate

: 817201-20-0
(1S,2S,3S,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-methyl-7-oxabicyclo[2.2.1]hept-5-ene

Guidance literature:: Multi-step reaction with 5 steps

1: lipase PS (Amano); H₂O / tetrahydrofuran / 480 h / 20 °C

2: imidazole / dimethylformamide / 23 h / 0 °C

3: 1.90 g / NaOMe / methanol / 2 h / 20 °C

4: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 22 h / 0 °C

5: 110 mg / NaBH₄; DMPU / 2 h / 90 °C

With 1H-imidazole; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; Lipase PS (Amano); water; sodium methylate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo048566j