(-)-(3aR,6aR)-3a-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)one

Base Information

Chemical Name:(-)-(3aR,6aR)-3a-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)one
CAS No.:579505-86-5
Molecular Formula:C₂₅H₃₀O₄Si
Molecular Weight:422.596
Hs Code.:

Synonyms:(-)-(3aR,6aR)-3a-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)one

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Chemical Property of (-)-(3aR,6aR)-3a-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)one

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Technology Process of (-)-(3aR,6aR)-3a-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)one

There total 14 articles about (-)-(3aR,6aR)-3a-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)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: 96.0%

: (+)-(3aS,4S,6aR)-3a-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

: 579505-86-5
(-)-(3aR,6aR)-3a-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)one

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 24h;
DOI:10.1016/j.carres.2015.08.003

Reference yield: 80.0%

: 579505-85-4
3a-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

: 579505-86-5
(-)-(3aR,6aR)-3a-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)one

Guidance literature:: With dipyridinium dichromate; In dichloromethane; at 0 - 20 ℃; for 30h;
DOI:10.1016/S0040-4039(03)01132-8

Reference yield:

: 67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1
2,3-O-isopropylidene-D-ribofuranose

: 579505-86-5
(-)-(3aR,6aR)-3a-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)one

Guidance literature:: Multi-step reaction with 10 steps

1: 70 percent / Et₃N / DMAP / CH₂Cl₂ / 10 h / 0 - 20 °C

2: 83 percent / K₂CO₃ / methanol / 10 h / 85 °C

3: 83 percent / imidazole / DMAP / CH₂Cl₂ / 3 h / 0 - 20 °C

4: 79 percent / NaH / tetrahydrofuran / 3 h / 0 - 20 °C

5: 53 percent / HCO₂H; Et₂O / 1 h / 0 - 20 °C

6: 65 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 12 h / 0 - 20 °C

7: Zn / tetrahydrofuran; H₂O / 5 h / 20 - 50 °C / sonication

8: tetrahydrofuran / 2 h / 0 °C

9: 80 percent / Grubbs' catalyst / CH₂Cl₂ / 6 h / 20 °C

10: 80 percent / PDC / CH₂Cl₂ / 30 h / 0 - 20 °C

With 1H-imidazole; dipyridinium dichromate; formic acid; diethyl ether; iodine; sodium hydride; potassium carbonate; triethylamine; triphenylphosphine; zinc; dmap; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1016/S0040-4039(03)01132-8