(3aRS,6RS,6aRS)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-cyclopenta[d][1,3]dioxol-4(5H)-one

Base Information

Chemical Name:(3aRS,6RS,6aRS)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-cyclopenta[d][1,3]dioxol-4(5H)-one
CAS No.:144874-60-2
Molecular Formula:C₂₅H₃₂O₄Si
Molecular Weight:424.612
Hs Code.:

Synonyms:(3aRS,6RS,6aRS)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-cyclopenta[d][1,3]dioxol-4(5H)-one

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Chemical Property of (3aRS,6RS,6aRS)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-cyclopenta[d][1,3]dioxol-4(5H)-one

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Technology Process of (3aRS,6RS,6aRS)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-cyclopenta[d][1,3]dioxol-4(5H)-one

There total 24 articles about (3aRS,6RS,6aRS)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-cyclopenta[d][1,3]dioxol-4(5H)-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: 92.0%

: tert-butyl(((3aR*,4R*,6aS*)-2,2-dimethyl-6-methylenetetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methoxy)diphenylsilane

: 144874-60-2
(3aRS,6RS,6aRS)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-cyclopenta[d][1,3]dioxol-4(5H)-one

Guidance literature:: tert-butyl(((3aR*,4R*,6aS*)-2,2-dimethyl-6-methylenetetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methoxy)diphenylsilane; With oxygen; ozone; In methanol; dichloromethane; at -78 ℃; Inert atmosphere;

With thiourea; In methanol; dichloromethane; at -78 - 25 ℃; for 3h; Inert atmosphere;
DOI:10.1021/acs.joc.6b02594

Reference yield:

: C₃₄H₅₀O₆Si₂

: 144874-60-2
(3aRS,6RS,6aRS)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-cyclopenta[d][1,3]dioxol-4(5H)-one

Guidance literature:: C₃₄H₅₀O₆Si₂; With oxygen; ozone; In dichloromethane; at -78 - -25 ℃; Inert atmosphere;

With dimethylsulfide; In dichloromethane; at -78 - 20 ℃; for 4h; Inert atmosphere;
DOI:10.1016/j.tetlet.2014.05.030

Reference yield:

: 542-92-7,25568-84-7,7313-32-8
cyclopenta-1,3-diene

: 144874-60-2
(3aRS,6RS,6aRS)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-cyclopenta[d][1,3]dioxol-4(5H)-one

Guidance literature:: Multi-step reaction with 5 steps

1: 2.) imidazole, 4-(dimethylamino)pyridine / 2.) dichloromethane, 0 deg C, 3 h

2: 84 percent / N-Methylmorpholine N-oxide / osmium tetraoxide / acetone; H₂O; butan-1-ol / 15 h / Ambient temperature

3: 81 percent / p-toluenesulfonic acid / 3 h / Ambient temperature

4: 250 mg / imidazole, 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / 0 °C

5: 2.33 g / pyridinium chlorochromate, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

With 1H-imidazole; dmap; 4 A molecular sieve; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; pyridinium chlorochromate; osmium(VIII) oxide; In dichloromethane; water; acetone; butan-1-ol;