3-[(3aS,4S,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione

Base Information

Chemical Name:3-[(3aS,4S,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione
CAS No.:191805-04-6
Molecular Formula:C₂₈H₃₃NO₆Si
Molecular Weight:507.659
Hs Code.:

Synonyms:3-[(3aS,4S,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione

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Chemical Property of 3-[(3aS,4S,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione

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Technology Process of 3-[(3aS,4S,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione

There total 13 articles about 3-[(3aS,4S,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione 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: 42.0%

: 191805-03-5
(E)-3-[(3aS,4S,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-cyano-acrylic acid tert-butyl ester

: 191805-04-6
3-[(3aS,4S,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione

Guidance literature:: With trifluoroacetic anhydride; In trifluoroacetic acid; at 40 ℃; for 6h;
DOI:10.1007/BF00807307

Reference yield:

: Benzoic acid (3aR,6aS)-6a-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester

: 191805-04-6
3-[(3aS,4S,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione

Guidance literature:: Multi-step reaction with 3 steps

1: Me₃SiBr, CF₃SO₃SiMe₃ / CH₂Cl₂ / 20 h / 20 - 24 °C

2: 1) AIBN, (Me₃Si)3SiH, 2) 30percent H₂O₂, 0.5 M aq. Na₂CO₃ / 1) benzene, reflux, 2 h, 2) aq. acetone, r.t.

3: 1) 1.6 N BuLi, cyclohexyl(isopropyl)amine, PhSeCl, 2) NaIO₄ / 1) hexane, THF, -78 deg C to -20 deg C, 2) hexane, THF, MeOH, H₂O, -20 deg C to r.t., overnight

With sodium periodate; n-butyllithium; Phenylselenyl chloride; 2,2'-azobis(isobutyronitrile); trimethylsilyl bromide; trimethylsilyl trifluoromethanesulfonate; tris-(trimethylsilyl)silane; N-cyclohexylisopropylamine; dihydrogen peroxide; sodium carbonate; In dichloromethane;
DOI:10.1007/BF00807603

Reference yield:

: 70147-50-1
3-C-hydroxymethyl-2,3-O-isopropylidene-β-D-erythrofuranoside

: 191805-04-6
3-[(3aS,4S,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione

Guidance literature:: Multi-step reaction with 9 steps

1: 98 percent / pyridine / 16 h / Ambient temperature

2: 71 percent / Me₃SiOSO₂CF₃ / 48 h / Ambient temperature

3: 88 percent / NaOMe / 1.5 h / Ambient temperature

4: 83 percent / imidazole, DMAP / dimethylformamide / 1.5 h / Ambient temperature

5: 90 percent / LiI / pyridine / 16 h / Heating

6: SOCl₂ / diethyl ether; dimethylformamide / 0.75 h / Ambient temperature

7: CH₂Cl₂ / 2.5 h / -78 °C

8: CH₂Cl₂ / 16 h / -78 deg C to r.t.

9: 42 percent / trifluoroacetic anhydride / trifluoroacetic acid / 6 h / 40 °C

With pyridine; 1H-imidazole; dmap; thionyl chloride; trimethylsilyl trifluoromethanesulfonate; sodium methylate; trifluoroacetic anhydride; lithium iodide; In pyridine; diethyl ether; dichloromethane; N,N-dimethyl-formamide; trifluoroacetic acid;
DOI:10.1007/BF00807307