(+)-(1aR,1bS,4aS,5S,5aS)-3,3-dimethyl-1b-trityloxymethylhexahydro-2,4-dioxacyclopropa[a]pentalen-5-ol

Base Information

Chemical Name:(+)-(1aR,1bS,4aS,5S,5aS)-3,3-dimethyl-1b-trityloxymethylhexahydro-2,4-dioxacyclopropa[a]pentalen-5-ol
CAS No.:857896-69-6
Molecular Formula:C₂₉H₃₀O₄
Molecular Weight:442.555
Hs Code.:

Synonyms:(+)-(1aR,1bS,4aS,5S,5aS)-3,3-dimethyl-1b-trityloxymethylhexahydro-2,4-dioxacyclopropa[a]pentalen-5-ol

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Chemical Property of (+)-(1aR,1bS,4aS,5S,5aS)-3,3-dimethyl-1b-trityloxymethylhexahydro-2,4-dioxacyclopropa[a]pentalen-5-ol

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Technology Process of (+)-(1aR,1bS,4aS,5S,5aS)-3,3-dimethyl-1b-trityloxymethylhexahydro-2,4-dioxacyclopropa[a]pentalen-5-ol

There total 8 articles about (+)-(1aR,1bS,4aS,5S,5aS)-3,3-dimethyl-1b-trityloxymethylhexahydro-2,4-dioxacyclopropa[a]pentalen-5-ol 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: 62.0%

: 75-11-6
diiodomethane

: 474329-18-5
(+)-(3aS,4S,6aS)-2,2-dimethyl-6a-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

: 857896-69-6
(+)-(1aR,1bS,4aS,5S,5aS)-3,3-dimethyl-1b-trityloxymethylhexahydro-2,4-dioxacyclopropa[a]pentalen-5-ol

Guidance literature:: With diethylzinc; In hexane; dichloromethane; at 20 ℃;
DOI:10.1021/jo0503207

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

: 857896-69-6
(+)-(1aR,1bS,4aS,5S,5aS)-3,3-dimethyl-1b-trityloxymethylhexahydro-2,4-dioxacyclopropa[a]pentalen-5-ol

Guidance literature:: Multi-step reaction with 7 steps

1: tetrahydrofuran / 3 h / -78 - 0 °C

2: NaIO₄ / CH₂Cl₂; H₂O / 0.67 h / 0 - 20 °C

3: 95 percent / K₂CO₃ / methanol; H₂O / 36 h / 80 °C

4: t-BuOK / tetrahydrofuran / 20 °C

5: second generation Grubbs catalyst / CH₂Cl₂ / 2 h / 20 °C

6: 78 percent / DMAP; pyridine / 20 h / 20 °C

7: 62 percent / diethylzinc / CH₂Cl₂ / 9 h / 20 °C

With pyridine; dmap; sodium periodate; potassium tert-butylate; diethylzinc; potassium carbonate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; water; 1: Grignard reaction / 7: Simmons-Smith cyclopropanation;
DOI:10.1081/NCN-200060292

Reference yield:

: (3aS,6S,6aS)-2,2-dimethyl-6-vinyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol

: 857896-69-6
(+)-(1aR,1bS,4aS,5S,5aS)-3,3-dimethyl-1b-trityloxymethylhexahydro-2,4-dioxacyclopropa[a]pentalen-5-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / K₂CO₃ / methanol; H₂O / 36 h / 80 °C

2: t-BuOK / tetrahydrofuran / 20 °C

3: second generation Grubbs catalyst / CH₂Cl₂ / 2 h / 20 °C

4: 78 percent / DMAP; pyridine / 20 h / 20 °C

5: 62 percent / diethylzinc / CH₂Cl₂ / 9 h / 20 °C

With pyridine; dmap; potassium tert-butylate; diethylzinc; potassium carbonate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; water; 5: Simmons-Smith cyclopropanation;
DOI:10.1081/NCN-200060292