2-Cyclohexen-1-one,4-[(b-D-glucopyranosyloxy)methyl]-3-[(1E)-4-hydroxy-3-(hydroxymethyl)-1-butenyl]-2,4-dimethyl-,(4S)- (9CI)

Base Information

Chemical Name:2-Cyclohexen-1-one,4-[(b-D-glucopyranosyloxy)methyl]-3-[(1E)-4-hydroxy-3-(hydroxymethyl)-1-butenyl]-2,4-dimethyl-,(4S)- (9CI)
CAS No.:108543-38-0
Molecular Formula:C20H32 O9
Molecular Weight:416.469
Hs Code.:

Synonyms:2-Cyclohexen-1-one,4-[(b-D-glucopyranosyloxy)methyl]-3-[4-hydroxy-3-(hydroxymethyl)-1-butenyl]-2,4-dimethyl-,[S-(E)]-; (-)-Cassioside; Cassioside; Cassioside (Cinnamonum)

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Chemical Property of 2-Cyclohexen-1-one,4-[(b-D-glucopyranosyloxy)methyl]-3-[(1E)-4-hydroxy-3-(hydroxymethyl)-1-butenyl]-2,4-dimethyl-,(4S)- (9CI)

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MSDS Files:: SDS file from LookChem

Useful:

Technology Process of 2-Cyclohexen-1-one,4-[(b-D-glucopyranosyloxy)methyl]-3-[(1E)-4-hydroxy-3-(hydroxymethyl)-1-butenyl]-2,4-dimethyl-,(4S)- (9CI)

There total 10 articles about 2-Cyclohexen-1-one,4-[(b-D-glucopyranosyloxy)methyl]-3-[(1E)-4-hydroxy-3-(hydroxymethyl)-1-butenyl]-2,4-dimethyl-,(4S)- (9CI) 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: 80.0%

: 183279-64-3
(S)-2,4-Dimethyl-3-((E)-4-triisopropylsilanyloxy-3-triisopropylsilanyloxymethyl-but-1-enyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yloxymethyl]-cyclohex-2-enone

: 108543-38-0
(-)-cassioside

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile;
DOI:10.1021/jo961613q

Reference yield:

: 13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1
(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 108543-38-0
(-)-cassioside

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) K₂CO₃, 2.) NaH / methanol

2: 74 percent / dimethylformamide / rt, 4 h -> 100 deg C, 2 h

3: 96 percent / m-CPBA / CH₂Cl₂ / -78 deg C, 2 h -> rt, 12 h

4: CH₂Cl₂ / -90 °C

5: Pd(OAc)2, AgOTf, I₂ / acetonitrile; CH₂Cl₂ / Ambient temperature

6: NaI, Et₃N / acetone / Ambient temperature

7: 80 percent / CAN / acetonitrile; H₂O

With palladium diacetate; ammonium cerium(IV) nitrate; iodine; silver trifluoromethanesulfonate; sodium hydride; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/jo961613q

Reference yield:

: 183279-62-1
[(1S,2S)-1,3-Dimethyl-4-triisopropylsilanyloxy-2-((E)-4-triisopropylsilanyloxy-3-triisopropylsilanyloxymethyl-but-1-enyl)-cyclohex-3-enyl]-methanol

: 108543-38-0
(-)-cassioside

Guidance literature:: Multi-step reaction with 5 steps

1: 2,6-di-tert-butyl-4-methylpyridine, molecular sieves 4 Angstroems

2: CH₂Cl₂ / -90 °C

3: Pd(OAc)2, AgOTf, I₂ / acetonitrile; CH₂Cl₂ / Ambient temperature

4: NaI, Et₃N / acetone / Ambient temperature

5: 80 percent / CAN / acetonitrile; H₂O

With palladium diacetate; 2,6-di-tert-butyl-4-methylpyridine; ammonium cerium(IV) nitrate; 4 A molecular sieve; iodine; silver trifluoromethanesulfonate; triethylamine; sodium iodide; In dichloromethane; water; acetone; acetonitrile;
DOI:10.1021/jo961613q