2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohex-2-enone

Base Information

Chemical Name:2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohex-2-enone
CAS No.:892867-41-3
Molecular Formula:C₄₅H₅₆O₄Si
Molecular Weight:689.023
Hs Code.:

Synonyms:2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohex-2-enone

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Chemical Property of 2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohex-2-enone

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Technology Process of 2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohex-2-enone

There total 6 articles about 2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohex-2-enone 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: 86.0%

: 892867-40-2
((1S,2S,3R)-4-Benzyloxy-3-cyclohex-1-enyl-2,3-dimethyl-1-trityloxymethyl-butoxy)-tert-butyl-dimethyl-silane

: 892867-41-3
2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohex-2-enone

Guidance literature:: With selenium(IV) oxide; In 1,4-dioxane; water; at 90 ℃; for 17h;
DOI:10.1016/j.tetlet.2006.03.078

Reference yield:

: (3S,4S,5S)-3,4-Dimethyl-5-trityloxymethyl-dihydro-furan-2-one

: 892867-41-3
2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 5 steps

1.1: LDA / tetrahydrofuran / 0.17 h / -78 °C

1.2: 91 percent / SOCl₂; pyridine / 1 h / 0 °C

2.1: LiBH₄ / tetrahydrofuran / 38 h / 65 °C

3.1: K₂CO₃; 18-crown-6-ether / acetonitrile / 8 h / 50 °C

4.1: DBU / acetonitrile / 20 h / 65 °C

5.1: 86 percent / SeO₂ / dioxane; H₂O / 17 h / 90 °C

With lithium borohydride; selenium(IV) oxide; 18-crown-6 ether; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; water; acetonitrile;
DOI:10.1016/j.tetlet.2006.03.078

Reference yield:

: 892867-38-8
(3R,4S,5S)-3-Cyclohex-1-enyl-3,4-dimethyl-5-trityloxymethyl-dihydro-furan-2-one

: 892867-41-3
2-[(1R,2S,3S)-1-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1,2-dimethyl-4-trityloxy-butyl]-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 4 steps

1: LiBH₄ / tetrahydrofuran / 38 h / 65 °C

2: K₂CO₃; 18-crown-6-ether / acetonitrile / 8 h / 50 °C

3: DBU / acetonitrile / 20 h / 65 °C

4: 86 percent / SeO₂ / dioxane; H₂O / 17 h / 90 °C

With lithium borohydride; selenium(IV) oxide; 18-crown-6 ether; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; 1,4-dioxane; water; acetonitrile;
DOI:10.1016/j.tetlet.2006.03.078