threo-2-Hexulose, 1,4-anhydro-5,6-dideoxy-5-methyl-3-O-methyl- (9CI)

Base Information

• Chemical Name: threo-2-Hexulose, 1,4-anhydro-5,6-dideoxy-5-methyl-3-O-methyl- (9CI)
• CAS No.: 200347-37-1
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.197
• Mol file: 200347-37-1.mol

Synonyms:threo-2-Hexulose, 1,4-anhydro-5,6-dideoxy-5-methyl-3-O-methyl- (9CI)

Chemical Property of threo-2-Hexulose, 1,4-anhydro-5,6-dideoxy-5-methyl-3-O-methyl- (9CI)

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of threo-2-Hexulose, 1,4-anhydro-5,6-dideoxy-5-methyl-3-O-methyl- (9CI)

There total 5 articles about threo-2-Hexulose, 1,4-anhydro-5,6-dideoxy-5-methyl-3-O-methyl- (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: 67.0%

tert-Butyl-{1-[(4S,5S)-5-isopropyl-4-methoxy-dihydro-furan-(3E)-ylidene]-2,2-dimethyl-propoxy}-dimethyl-silane → (4S,5R)-5-Isopropyl-4-methoxy-dihydro-furan-3-one (200347-37-1)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; for 0.916667h; Ambient temperature;

DOI:10.1016/S0040-4039(97)10294-5

Reference yield:

1-methoxy-3-methyl-1-(phenylthio)-2-butanol (200347-21-3) → (4S,5R)-5-Isopropyl-4-methoxy-dihydro-furan-3-one (200347-37-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 67 percent / Aliquat 336, 50percent aq NaOH / CH₂Cl₂ / 3.3 h / Ambient temperature

2: 95 percent / KHMDS / tetrahydrofuran / 0.75 h

3: 22 percent Spectr_. / dimethyl(thiomethyl)sulfonium tetrafluoroborate, DBU / CH₂Cl₂

4: 84 percent / KHMDS / toluene / 0.58 h

5: 67 percent / NaIO₄, RuCl₃*H₂O / CCl₄; acetonitrile; H₂O / 0.92 h / Ambient temperature

With ruthenium trichloride; sodium hydroxide; sodium periodate; dimethyl(methylthio)sulfonium tetrafluoroborate; potassium hexamethylsilazane; Aliquat 336; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; toluene; acetonitrile;

DOI:10.1016/S0040-4039(97)10294-5

Reference yield:

1-[1-(Methoxy-phenylsulfanyl-methyl)-2-methyl-propoxy]-4,4-dimethyl-pentan-3-one (200347-25-7) → (4S,5R)-5-Isopropyl-4-methoxy-dihydro-furan-3-one (200347-37-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / KHMDS / tetrahydrofuran / 0.75 h

2: 22 percent Spectr_. / dimethyl(thiomethyl)sulfonium tetrafluoroborate, DBU / CH₂Cl₂

3: 84 percent / KHMDS / toluene / 0.58 h

4: 67 percent / NaIO₄, RuCl₃*H₂O / CCl₄; acetonitrile; H₂O / 0.92 h / Ambient temperature

With ruthenium trichloride; sodium periodate; dimethyl(methylthio)sulfonium tetrafluoroborate; potassium hexamethylsilazane; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; toluene; acetonitrile;

DOI:10.1016/S0040-4039(97)10294-5

upstream raw materials:

1-methoxy-3-methyl-1-(phenylthio)-2-butanol

1-[1-(Methoxy-phenylsulfanyl-methyl)-2-methyl-propoxy]-4,4-dimethyl-pentan-3-one

tert-Butyl-{(Z)-1-tert-butyl-3-[1-(methoxy-phenylsulfanyl-methyl)-2-methyl-propoxy]-propenyloxy}-dimethyl-silane

Downstream raw materials:

(3R,4R,5R)-5-Isopropyl-4-methoxy-tetrahydro-furan-3-ol