(5R,6R)-(+)-5-(2',5'-Dihydro-2'-oxo-3'-furanyl)-6-hydroxymethyl-1-cyclohexene-1-carboxylic Acid

Base Information

• Chemical Name: (5R,6R)-(+)-5-(2',5'-Dihydro-2'-oxo-3'-furanyl)-6-hydroxymethyl-1-cyclohexene-1-carboxylic Acid
• CAS No.: 151062-75-8
• Molecular Formula: C₁₂H₁₄O₅
• Molecular Weight: 238.24
• Mol file: 151062-75-8.mol

Synonyms:(5R,6R)-(+)-5-(2',5'-Dihydro-2'-oxo-3'-furanyl)-6-hydroxymethyl-1-cyclohexene-1-carboxylic Acid

Chemical Property of (5R,6R)-(+)-5-(2',5'-Dihydro-2'-oxo-3'-furanyl)-6-hydroxymethyl-1-cyclohexene-1-carboxylic Acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6R)-(+)-5-(2',5'-Dihydro-2'-oxo-3'-furanyl)-6-hydroxymethyl-1-cyclohexene-1-carboxylic Acid

There total 14 articles about (5R,6R)-(+)-5-(2',5'-Dihydro-2'-oxo-3'-furanyl)-6-hydroxymethyl-1-cyclohexene-1-carboxylic Acid 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: 78.0%

(+)-3-<(1'R,2'R)-2'-Hydroxymethyl-3'-formyl-3'-cyclohexenyl>-2(5H)-furanone (151062-74-7) → (5R,6R)-(+)-5-(2',5'-Dihydro-2'-oxo-3'-furanyl)-6-hydroxymethyl-1-cyclohexene-1-carboxylic Acid (151062-75-8)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; for 24h; Ambient temperature;

Reference yield:

(1S,2R,6R,7S,9S)-(+)-9-Hydroxy-4-oxatricyclo<5.2.2.02,6>undecan-3-one (151062-62-3) → (5R,6R)-(+)-5-(2',5'-Dihydro-2'-oxo-3'-furanyl)-6-hydroxymethyl-1-cyclohexene-1-carboxylic Acid (151062-75-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 98 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / Ambient temperature

2: 98 percent / LiAlH₄ / tetrahydrofuran / 2.5 h / Ambient temperature

3: 1) NaH, 2) (nBu)4NI / 1) DMF, r.t., 1 h, 2) r.t., 4 h

4: 98 percent / p-toluenesulfonic acid monohydrate (p-TsOH) / methanol / 6 h / Ambient temperature

5: 82 percent / pyridinium dichromate / CH₂Cl₂ / 8 h / Ambient temperature

7: 4-(dimethylamine)pyridine (DMAP), trifluoromethanesulfonyl chloride (TfCl), / CH₂Cl₂ / 1) 0 deg C, 15 min, 2) r.t., 3 h

8: 1) Li-diisopropylamide (LDA), N,N,N',N'-tetramethylethylenediamine (TMEDA) / 1) THF, -78 deg C, 0.5 h, 2) a) -78 deg C, 0.5 h, b) 0 deg C, 9 h

9: 75 percent / p-toluenesulfonic acid monohydrate (p-TsOH) / methanol / 4 h / Ambient temperature

10: 1) Li diisopropylamide (LDA), N,N,N',N'-tetramethylethylenediamine (TMEDA) / 1) hexane, THF, -78 deg C, 0.5 h, 2) a) -78 deg C, 0.5 h, b) 0 deg C, 2 h

11: 95 percent / m-chloroperbenzoic acid (MCPBA) / CH₂Cl₂ / 1 h / -70 °C

12: 50 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH₂Cl₂; H₂O / 24 h / Ambient temperature

13: 78 percent / NaClO₂, 2-methyl-2-butene, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 24 h / Ambient temperature

With dmap; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; dipyridinium dichromate; 2-methyl-but-2-ene; N,N,N,N,-tetramethylethylenediamine; trifluoromethane sulfonyl chloride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol;

Reference yield:

(1S,2S,4S,5R,6R)-(+)-5,6-Bis(hydroxymethyl)-2-(tetrahydro-2H-pyran-2-yloxy)bicyclo<2.2.2>octane → (5R,6R)-(+)-5-(2',5'-Dihydro-2'-oxo-3'-furanyl)-6-hydroxymethyl-1-cyclohexene-1-carboxylic Acid (151062-75-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) NaH, 2) (nBu)4NI / 1) DMF, r.t., 1 h, 2) r.t., 4 h

2: 98 percent / p-toluenesulfonic acid monohydrate (p-TsOH) / methanol / 6 h / Ambient temperature

3: 82 percent / pyridinium dichromate / CH₂Cl₂ / 8 h / Ambient temperature

5: 4-(dimethylamine)pyridine (DMAP), trifluoromethanesulfonyl chloride (TfCl), / CH₂Cl₂ / 1) 0 deg C, 15 min, 2) r.t., 3 h

6: 1) Li-diisopropylamide (LDA), N,N,N',N'-tetramethylethylenediamine (TMEDA) / 1) THF, -78 deg C, 0.5 h, 2) a) -78 deg C, 0.5 h, b) 0 deg C, 9 h

7: 75 percent / p-toluenesulfonic acid monohydrate (p-TsOH) / methanol / 4 h / Ambient temperature

8: 1) Li diisopropylamide (LDA), N,N,N',N'-tetramethylethylenediamine (TMEDA) / 1) hexane, THF, -78 deg C, 0.5 h, 2) a) -78 deg C, 0.5 h, b) 0 deg C, 2 h

9: 95 percent / m-chloroperbenzoic acid (MCPBA) / CH₂Cl₂ / 1 h / -70 °C

10: 50 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH₂Cl₂; H₂O / 24 h / Ambient temperature

11: 78 percent / NaClO₂, 2-methyl-2-butene, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 24 h / Ambient temperature

With dmap; sodium chlorite; sodium dihydrogenphosphate; dipyridinium dichromate; 2-methyl-but-2-ene; N,N,N,N,-tetramethylethylenediamine; trifluoromethane sulfonyl chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In methanol; dichloromethane; water; tert-butyl alcohol;

upstream raw materials:

(+)-3-<(1'R,2'R)-2'-Hydroxymethyl-3'-formyl-3'-cyclohexenyl>-2(5H)-furanone

(1S,2R,6R,7S,9S)-(+)-9-Hydroxy-4-oxatricyclo<5.2.2.0^2,6>undecan-3-one

(1S,2S,4S,5R,6R)-(+)-5,6-Bis(benzyloxymethyl)bicyclo<2.2.2>octan-2-ol

Methyl (1'S,2'R,3'R,4'S)-(+)-2',3'-Bis(benzyloxymethyl)-4'-hydroxycyclohexylacetate

Downstream raw materials:

(+)-Differolide