(4R,5S,6S)-4,5,6-Tris-benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-cyclohex-2-enone

Base Information

Chemical Name:(4R,5S,6S)-4,5,6-Tris-benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-cyclohex-2-enone
CAS No.:304672-03-5
Molecular Formula:C₃₃H₃₆O₆
Molecular Weight:528.645
Hs Code.:

Synonyms:(4R,5S,6S)-4,5,6-Tris-benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-cyclohex-2-enone

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Chemical Property of (4R,5S,6S)-4,5,6-Tris-benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-cyclohex-2-enone

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Technology Process of (4R,5S,6S)-4,5,6-Tris-benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-cyclohex-2-enone

There total 1 articles about (4R,5S,6S)-4,5,6-Tris-benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-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: 85.0%

: 304672-00-2
(2S,3S,4R)-2,3,4-Tris-benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5-hydroxy-cyclohexanone

: 304672-03-5
(4R,5S,6S)-4,5,6-Tris-benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-cyclohex-2-enone

Guidance literature:: With methanesulfonyl chloride; triethylamine; In dichloromethane; at 20 ℃; for 3h;
DOI:10.3987/com-00-8987

Reference yield: 65.0%

: 304672-03-5
(4R,5S,6S)-4,5,6-Tris-benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-cyclohex-2-enone

: 304672-04-6
(3S,4S,5S)-3,4,5-Tris-benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-7-oxa-bicyclo[4.1.0]heptan-2-one

Guidance literature:: With dihydrogen peroxide; potassium carbonate; In tetrahydrofuran; water; at 0 ℃; for 6h;
DOI:10.3987/com-00-8987

Reference yield:

: 304672-03-5
(4R,5S,6S)-4,5,6-Tris-benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-cyclohex-2-enone

: (4R,5S,6S)-4,5,6-Tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 5 steps

1: 65 percent / 30 percent H₂O₂; K₂CO₃ / H₂O; tetrahydrofuran / 6 h / 0 °C

2: 93 percent / NaBH₄ / methanol / 0.25 h / -40 °C

3: 98 percent / benzene / 12 h / 80 °C

4: 30 percent / Bu₃SnH; AIBN / benzene / 4 h / 80 °C

5: 87 percent / MnO₂ / CH₂Cl₂ / 45 °C

With manganese(IV) oxide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; water; benzene;
DOI:10.3987/com-00-8987