2-Cyclohexen-1-one,3-[(1E)-4-hydroxy-3-(hydroxymethyl)-1-buten-1-yl]-4-(hydroxymethyl)-2,4-dimethyl-,(4S)-

Base Information

• Chemical Name: 2-Cyclohexen-1-one,3-[(1E)-4-hydroxy-3-(hydroxymethyl)-1-buten-1-yl]-4-(hydroxymethyl)-2,4-dimethyl-,(4S)-
• CAS No.: 117479-71-7
• Molecular Formula: C14H22 O4
• Molecular Weight: 254.326
• Mol file: 117479-71-7.mol

Synonyms:2-Cyclohexen-1-one,3-[(1E)-4-hydroxy-3-(hydroxymethyl)-1-butenyl]-4-(hydroxymethyl)-2,4-dimethyl-,(4S)- (9CI); 2-Cyclohexen-1-one,3-[4-hydroxy-3-(hydroxymethyl)-1-butenyl]-4-(hydroxymethyl)-2,4-dimethyl-,[S-(E)]-; (+)-Cassiol; (S)-(+)-Cassiol; Cassiol

Chemical Property of 2-Cyclohexen-1-one,3-[(1E)-4-hydroxy-3-(hydroxymethyl)-1-buten-1-yl]-4-(hydroxymethyl)-2,4-dimethyl-,(4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Cyclohexen-1-one,3-[(1E)-4-hydroxy-3-(hydroxymethyl)-1-buten-1-yl]-4-(hydroxymethyl)-2,4-dimethyl-,(4S)-

There total 66 articles about 2-Cyclohexen-1-one,3-[(1E)-4-hydroxy-3-(hydroxymethyl)-1-buten-1-yl]-4-(hydroxymethyl)-2,4-dimethyl-,(4S)- 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%

(S)-3-[(E)-2-(2,2-Dimethyl-[1,3]dioxan-5-yl)-vinyl]-4-hydroxymethyl-2,4-dimethyl-cyclohex-2-enone (155818-07-8) → (+)-Cassiol (117479-71-7)

Guidance literature:

With hydrogenchloride; at 23 ℃; for 0.5h;

DOI:10.1021/ja00087a062

Reference yield: 73.0%

(2S,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-[(E)-2-(2,2-dimethyl-[1,3]dioxan-5-yl)-vinyl]-3-hydroxy-2,4-dimethyl-cyclohexanone (185903-70-2) → (+)-Cassiol (117479-71-7)

Guidance literature:

With pyridine hydrogenfluoride; In pyridine; acetonitrile;

DOI:10.1016/S0040-4039(96)02191-0

Reference yield: 72.0%

(S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-[(E)-2-(2,2-dimethyl-[1,3]dioxan-5-yl)-vinyl]-2,4-dimethyl-cyclohex-2-enone (123522-74-7) → (+)-Cassiol (117479-71-7)

Guidance literature:

With pyridine hydrogenfluoride; In pyridine; at 70 ℃;

DOI:10.1016/S0040-4039(01)80292-6

upstream raw materials:

Tributyl-[(E)-2-(2,2-dimethyl-[1,3]dioxan-5-yl)-vinyl]-stannane

(R)-6-(t-Butyldimethylsiloxymethyl)-3-ethoxy-2,6-dimethyl-2-cyclohexen-1-one

(-)-cassioside

(S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-[(E)-2-(2,2-dimethyl-[1,3]dioxan-5-yl)-vinyl]-2,4-dimethyl-cyclohex-2-enone

Downstream raw materials:

(4S)-2,4-dimethyl-3-(3,3-bis-methoxycarbonylpropyl)-4-methoxycarbonyl-2-cyclohexen-1-one

(4S)-2,4-dimethyl-3-(4-hydroxy-3-hydroxymethyl-butyl)-4-hydroxymethyl-2-cyclohexen-1-one

Refernces

Enantioselective total synthesis of (+)-cassiol

10.1021/ol802410t

The research focuses on the enantioselective total synthesis of (+)-cassiol, a sesquiterpenoid with potent antiulcerogenic activity. The purpose of the study was to develop an efficient and convergent synthetic route to (+)-cassiol, which features a challenging all-carbon quaternary stereocenter. The researchers successfully achieved this through a series of reactions, including decarboxylative alkylation, isomerization, oxidative olefin cleavage, and a Stork-Danheiser-type addition/rearrangement. Key chemicals used in the process include Pd2(pmdba)3 as a catalyst, (R)-t-BuPHOX as a ligand, iodomethane for alkylation, PdCl2(CH3CN)2 for isomerization, and DABCO as a ligand in the dihydroxylation step. The synthesis involved a linear sequence of eight steps, starting from vinylogous thioester 4, and resulted in a 12% overall yield of (+)-cassiol. The final product's spectroscopic data matched that of the natural product, confirming the success of the synthesis.