(1S,2S,5S,6R,7R)-2-t-butyldiphenylsilyloxy-6-hydroxy-7-tetrahydropyranyloxybicyclo<3.3.0>octane

Base Information

Chemical Name:(1S,2S,5S,6R,7R)-2-t-butyldiphenylsilyloxy-6-hydroxy-7-tetrahydropyranyloxybicyclo<3.3.0>octane
CAS No.:142473-16-3
Molecular Formula:C₃₀H₄₂O₄Si
Molecular Weight:494.747
Hs Code.:

Synonyms:(1S,2S,5S,6R,7R)-2-t-butyldiphenylsilyloxy-6-hydroxy-7-tetrahydropyranyloxybicyclo<3.3.0>octane

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Chemical Property of (1S,2S,5S,6R,7R)-2-t-butyldiphenylsilyloxy-6-hydroxy-7-tetrahydropyranyloxybicyclo<3.3.0>octane

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Technology Process of (1S,2S,5S,6R,7R)-2-t-butyldiphenylsilyloxy-6-hydroxy-7-tetrahydropyranyloxybicyclo<3.3.0>octane

There total 8 articles about (1S,2S,5S,6R,7R)-2-t-butyldiphenylsilyloxy-6-hydroxy-7-tetrahydropyranyloxybicyclo<3.3.0>octane 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:

: (1R,2R,3aS,4S,6aS)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalene-1-carboxylic acid methyl ester

: 142473-16-3
(1S,2S,5S,6R,7R)-2-t-butyldiphenylsilyloxy-6-hydroxy-7-tetrahydropyranyloxybicyclo<3.3.0>octane

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -30 ℃; for 2h; Yield given;
DOI:10.1080/00397919208021612

Reference yield:

: 110-87-2
3,4-dihydro-2H-pyran

: 142473-16-3
(1S,2S,5S,6R,7R)-2-t-butyldiphenylsilyloxy-6-hydroxy-7-tetrahydropyranyloxybicyclo<3.3.0>octane

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 24 h

2: 96.5 percent / K₂CO₃ / methanol / 8 h

3: N,N-dimethylamino-pyridine, imidazole / dimethylformamide / 24 h / Ambient temperature

4: diisobutylaluminium hydride / toluene / 2 h / -30 °C

With 1H-imidazole; dmap; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1080/00397919208021612

Reference yield:

: 84937-33-7,142561-05-5
(1R,4R,5S)-(-)-4-carbomethoxytricyclo<3.3.0.0^2,8>octan-3-one

: 142473-16-3
(1S,2S,5S,6R,7R)-2-t-butyldiphenylsilyloxy-6-hydroxy-7-tetrahydropyranyloxybicyclo<3.3.0>octane

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / conc. H₂SO₄ / 5 h

2: 90 percent / NaBH₄ / aq. ethanol / 4 h / -50 °C

3: 99 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 24 h

4: 96.5 percent / K₂CO₃ / methanol / 8 h

5: N,N-dimethylamino-pyridine, imidazole / dimethylformamide / 24 h / Ambient temperature

6: diisobutylaluminium hydride / toluene / 2 h / -30 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; sulfuric acid; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1080/00397919208021612