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

Base Information

• Chemical Name: (1S,2R,3R,4R,5R)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-9-oxabicyclo[3.3.1]nonane-1,4-diol
• CAS No.: 878550-24-4
• Molecular Formula: C₂₂H₃₆O₆Si
• Molecular Weight: 424.61

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

Chemical Property of (1S,2R,3R,4R,5R)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-9-oxabicyclo[3.3.1]nonane-1,4-diol

Chemical Property:

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Technology Process of (1S,2R,3R,4R,5R)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-9-oxabicyclo[3.3.1]nonane-1,4-diol

There total 1 articles about (1S,2R,3R,4R,5R)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-9-oxabicyclo[3.3.1]nonane-1,4-diol 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: 56.0%

(2R,3R,4Z)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)cyclooct-4-enone → (1R,2R,3R,4R,5R)-3-(4-methoxybenzyloxy)-1-((tert-butyl)dimethylsilyloxy)-9-oxabicyclo[3.3.1]nonane-2,4-diol + (1S,2R,3R,4R,5R)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-9-oxabicyclo[3.3.1]nonane-1,4-diol (878550-24-4) + (1R,2R,3R,4S,5S)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-9-oxabicyclo[3.3.1]nonane-1,4-diol (878550-23-3)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; at 20 ℃; for 72h;

DOI:10.1021/jo051989g

Reference yield: 83.0%

(1S,2R,3R,4R,5R)-3-(4-methoxybenzyloxy)-2-((tert-butyl)dimethylsilyloxy)-9-oxabicyclo[3.3.1]nonane-1,4-diol (878550-24-4) + 2,2-dimethoxy-propane (77-76-9) → (3aR,4R,5R,9aR)-4-(4-methoxybenzyloxy)-5-((tert-butyl)dimethylsilyloxy)-2,2-dimethylhexahydrocycloocta[d][1,3]dioxol-6(3aH)-one (878550-28-8)

Guidance literature:

With pyridinium p-toluenesulfonate; for 4h; Heating;

DOI:10.1021/jo051989g

Reference yield: 80.0%

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

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jo051989g

Downstream raw materials:

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

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

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

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