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

Base Information

Chemical Name:(1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-(p-toluenesulfonyloxy)methyl-7-oxabicyclo[2.2.1]hept-5-ene
CAS No.:817201-21-1
Molecular Formula:C₃₁H₃₆O₅SSi
Molecular Weight:548.775
Hs Code.:

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

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

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

There total 10 articles about (1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-(p-toluenesulfonyloxy)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: 100.0%

: 816455-25-1
(1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene

: 98-59-9
p-toluenesulfonyl chloride

: 817201-21-1
(1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-(p-toluenesulfonyloxy)methyl-7-oxabicyclo[2.2.1]hept-5-ene

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 22h;
DOI:10.1021/jo048566j

Reference yield:

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

: 817201-21-1
(1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-(p-toluenesulfonyloxy)methyl-7-oxabicyclo[2.2.1]hept-5-ene

Guidance literature:: Multi-step reaction with 6 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

With pyridine; 1H-imidazole; dmap; 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

: 817201-21-1
(1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-(p-toluenesulfonyloxy)methyl-7-oxabicyclo[2.2.1]hept-5-ene

Guidance literature:: Multi-step reaction with 5 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

With pyridine; 1H-imidazole; dmap; Lipase PS (Amano); water; sodium methylate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo048566j