(1S,5R,6S)-(+)-1-hydroxy-6-(2-methoxy-4,5-methylenedioxyphenyl)-3,7-dioxabicyclo<3.3.0>octan-2-one

Base Information

• Chemical Name: (1S,5R,6S)-(+)-1-hydroxy-6-(2-methoxy-4,5-methylenedioxyphenyl)-3,7-dioxabicyclo<3.3.0>octan-2-one
• CAS No.: 107022-96-8
• Molecular Formula: C₁₄H₁₄O₇
• Molecular Weight: 294.261
• Mol file: 107022-96-8.mol

Synonyms:(1S,5R,6S)-(+)-1-hydroxy-6-(2-methoxy-4,5-methylenedioxyphenyl)-3,7-dioxabicyclo<3.3.0>octan-2-one

Chemical Property of (1S,5R,6S)-(+)-1-hydroxy-6-(2-methoxy-4,5-methylenedioxyphenyl)-3,7-dioxabicyclo<3.3.0>octan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5R,6S)-(+)-1-hydroxy-6-(2-methoxy-4,5-methylenedioxyphenyl)-3,7-dioxabicyclo<3.3.0>octan-2-one

There total 1 articles about (1S,5R,6S)-(+)-1-hydroxy-6-(2-methoxy-4,5-methylenedioxyphenyl)-3,7-dioxabicyclo<3.3.0>octan-2-one 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:

2-methoxy-4,5-methylenedioxybenzaldehyde (5780-00-7) → (1S,5R,6S)-(+)-1-hydroxy-6-(2-methoxy-4,5-methylenedioxyphenyl)-3,7-dioxabicyclo<3.3.0>octan-2-one (107022-96-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 98 percent / tetrahydrofuran / 3 h / -75 °C

2: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / -30 °C

3: 82 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 0.5 h / -10 °C

4: 1.) osmium tetroxide; 2.) sodium periodate / 1.) room temp., 15 h, acetone-t.BuOH-H₂O; 2.) room temp., 3 h, EtOAc-H₂O

5: Ag₂CO₃-celite, / benzene / 0.75 h / Heating

6: Et₃N / benzene / 4 h / Ambient temperature

7: DBU / benzene / 0.5 h / Ambient temperature

8: 4-methylmorpholine N-oxide / osmium tetroxide / acetone; 2-methyl-propan-2-ol; H₂O / 12 h / Ambient temperature

9: n-Bu₄NF, / tetrahydrofuran / 2 h / 0 °C

10: 59 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 3 h / Ambient temperature

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; silver carbonate; osmium(VIII) oxide; (1S)-10-camphorsulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; tert-butyl alcohol; benzene;

DOI:10.1246/cl.1986.1771

Reference yield:

(1S,5R,6S)-(+)-1-hydroxy-6-(2-methoxy-4,5-methylenedioxyphenyl)-3,7-dioxabicyclo<3.3.0>octan-2-one (107022-96-8) → (-)-isophrymarolin I (38303-95-6,123409-05-2,126373-81-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 18 h / Ambient temperature

2: 99 percent / DIBAL / toluene / 1 h / -75 °C

3: 92 percent / 2-fluoro-1-methylpyridinium tosylate, Et₃N / CH₂Cl₂ / 0.83 h / Ambient temperature

4: 50 percent / TrClO₄, SnCl₂, 4A molecular sive / diethyl ether / 2.5 h / 0 - 5 °C

5: 21 percent / n-Bu₄NF / CH₂Cl₂ / 1.5 h / Ambient temperature

6: DMAP / 12 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; Cl⁽³⁾HO₄; 4A molecular sive; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; 1-methyl-2-fluoropyridinium p-toluenesulfonate; triethylamine; tin(ll) chloride; In diethyl ether; dichloromethane; toluene;

DOI:10.1246/bcsj.61.4361

upstream raw materials:

2-methoxy-4,5-methylenedioxybenzaldehyde

Downstream raw materials:

(-)-isophrymarolin I