(3aR,4R,5R,9aR)-4-(4-methoxybenzyloxy)-5-((tert-butyl)dimethylsilyloxy)-2,2-dimethylhexahydrocycloocta[d][1,3]dioxol-6(3aH)-one

Base Information

Chemical Name:(3aR,4R,5R,9aR)-4-(4-methoxybenzyloxy)-5-((tert-butyl)dimethylsilyloxy)-2,2-dimethylhexahydrocycloocta[d][1,3]dioxol-6(3aH)-one
CAS No.:878550-28-8
Molecular Formula:C₂₅H₄₀O₆Si
Molecular Weight:464.674
Hs Code.:

Synonyms:(3aR,4R,5R,9aR)-4-(4-methoxybenzyloxy)-5-((tert-butyl)dimethylsilyloxy)-2,2-dimethylhexahydrocycloocta[d][1,3]dioxol-6(3aH)-one

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Chemical Property of (3aR,4R,5R,9aR)-4-(4-methoxybenzyloxy)-5-((tert-butyl)dimethylsilyloxy)-2,2-dimethylhexahydrocycloocta[d][1,3]dioxol-6(3aH)-one

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Technology Process of (3aR,4R,5R,9aR)-4-(4-methoxybenzyloxy)-5-((tert-butyl)dimethylsilyloxy)-2,2-dimethylhexahydrocycloocta[d][1,3]dioxol-6(3aH)-one

There total 1 articles about (3aR,4R,5R,9aR)-4-(4-methoxybenzyloxy)-5-((tert-butyl)dimethylsilyloxy)-2,2-dimethylhexahydrocycloocta[d][1,3]dioxol-6(3aH)-one 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: 83.0%

: 878550-24-4
(1S,2R,3R,4R,5R)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-9-oxabicyclo[3.3.1]nonane-1,4-diol

: 77-76-9
2,2-dimethoxy-propane

: 878550-28-8
(3aR,4R,5R,9aR)-4-(4-methoxybenzyloxy)-5-((tert-butyl)dimethylsilyloxy)-2,2-dimethylhexahydrocycloocta[d][1,3]dioxol-6(3aH)-one

Guidance literature:: With pyridinium p-toluenesulfonate; for 4h; Heating;
DOI:10.1021/jo051989g

Reference yield: 50.0%

: 878550-28-8
(3aR,4R,5R,9aR)-4-(4-methoxybenzyloxy)-5-((tert-butyl)dimethylsilyloxy)-2,2-dimethylhexahydrocycloocta[d][1,3]dioxol-6(3aH)-one

: 19493-09-5
Methylenetriphenylphosphorane

: 878550-29-9
((3aR,4R,5S,9aR)-4-(4-methoxybenzyloxy)-2,2-dimethyl-6-methyleneoctahydrocycloocta[d][1,3]dioxol-5-yloxy)(tert-butyl)-dimethylsilane

Guidance literature:: In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1021/jo051989g

Reference yield:

: 878550-28-8
(3aR,4R,5R,9aR)-4-(4-methoxybenzyloxy)-5-((tert-butyl)dimethylsilyloxy)-2,2-dimethylhexahydrocycloocta[d][1,3]dioxol-6(3aH)-one

: 878550-30-2
((3aR,4R,5S,6R,9aR)-4-(4-methoxybenzyloxy)-5-((tert-butyl)dimethylsilyloxy)-2,2-dimethyloctahydrocycloocta[d][1,3]dioxol-6-yl)methanol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 50 percent / tetrahydrofuran / 2 h / 0 °C

2.1: borane tetrahydrofuran complex / tetrahydrofuran / 0 - 20 °C

2.2: 65 percent / NaOH; H₂O₂ / tetrahydrofuran; ethanol / 2 h / 20 °C

With borane-THF; In tetrahydrofuran;
DOI:10.1021/jo051989g