(-)-isophrymarolin I

Base Information

• Chemical Name: (-)-isophrymarolin I
• CAS No.: 126373-81-7
• Molecular Formula: C₂₄H₂₄O₁₁
• Molecular Weight: 488.448
• Mol file: 126373-81-7.mol

Synonyms:

Chemical Property of (-)-isophrymarolin I

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-isophrymarolin I

There total 18 articles about (-)-isophrymarolin I 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) → (-)-isophrymarolin I (38303-95-6,123409-05-2,126373-81-7)

Guidance literature:

Multi-step reaction with 15 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

11: 85 percent / 2,6-lutidine / CH₂Cl₂ / 18 h / Ambient temperature

12: 98 percent / i-Bu₂AlH / toluene / 1 h / -75 °C

13: SnCl₂/TrClO₄/4A molecular sive / diethyl ether / 2.5 h / 0 °C

14: n-BuNF, / tetrahydrofuran / 3 h / Ambient temperature

15: 4-(dimetylamino)pyridine / 12 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; TrClO₄/4A molecular sive; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; silver carbonate; tin(ll) chloride; osmium(VIII) oxide; (1S)-10-camphorsulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; toluene; tert-butyl alcohol; benzene;

DOI:10.1246/cl.1986.1771

Reference yield:

(3S,4R)-3-Hydroxy-4-[hydroxy-(6-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-3-hydroxymethyl-dihydro-furan-2-one (107022-95-7,107080-51-3,110903-01-0) → (-)-isophrymarolin I (38303-95-6,123409-05-2,126373-81-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 59 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 3 h / Ambient temperature

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

3: 99 percent / DIBAL / toluene / 1 h / -75 °C

4: 92 percent / 2-fluoro-1-methylpyridinium tosylate, Et₃N / CH₂Cl₂ / 0.83 h / Ambient temperature

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

6: 21 percent / n-Bu₄NF / CH₂Cl₂ / 1.5 h / Ambient temperature

7: DMAP / 12 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; Cl⁽³⁾HO₄; 4A molecular sive; (1S)-10-camphorsulfonic acid; 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

Reference yield:

(3R,4S)-3-<(1R/S)-1-<(t-butyldimethylsilyl)-oxy>-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl>-4-ethenyldihydro-2(3H)-furanone (107022-89-9,107080-46-6,110902-95-9,110902-96-0) → (-)-isophrymarolin I (38303-95-6,123409-05-2,126373-81-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 82 percent / LiAlH₄ / tetrahydrofuran; diethyl ether / 0.5 h / -10 °C

2: 1.) N-methylmorpholine N-oxide monohydrate, 2percent aq. OsO₄; 2.) NaIO₄ / 1.) acetone, t-BuOH, water, RT, 15 h; 2.) water, RT, 3 h

3: 91 percent / silver carbonate on Celite / benzene / 0.75 h / Heating

4: 1.) methanesulfonyl chloride, Et₃N; 2.) DBU / 1.) benzene, RT, 4 h; 2.) 30 min

5: 97 percent / N-methylmorpholine N-oxide monohydrate, 2 percent aq. OsO₄ / acetone; 2-methyl-propan-2-ol; H₂O / 12 h / Ambient temperature

6: n-Bu₄NF / tetrahydrofuran / 2 h / 0 °C

7: 59 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 3 h / Ambient temperature

8: 85 percent / 2,6-lutidine / CH₂Cl₂ / 18 h / Ambient temperature

9: 99 percent / DIBAL / toluene / 1 h / -75 °C

10: 92 percent / 2-fluoro-1-methylpyridinium tosylate, Et₃N / CH₂Cl₂ / 0.83 h / Ambient temperature

11: 50 percent / TrClO₄, SnCl₂, 4A molecular sive / diethyl ether / 2.5 h / 0 - 5 °C

12: 21 percent / n-Bu₄NF / CH₂Cl₂ / 1.5 h / Ambient temperature

13: DMAP / 12 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; Cl⁽³⁾HO₄; 4A molecular sive; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; 1-methyl-2-fluoropyridinium p-toluenesulfonate; methanesulfonyl chloride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; silver carbonate; tin(ll) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; toluene; tert-butyl alcohol; benzene;

DOI:10.1246/bcsj.61.4361

upstream raw materials:

acetic anhydride

(1S,3aS,4S,6aR)-1-(6-Methoxy-benzo[1,3]dioxol-5-yl)-4-(6-methoxy-benzo[1,3]dioxol-5-yloxy)-dihydro-furo[3,4-c]furan-3a-ol

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

(3S,4R)-3-Hydroxy-4-[hydroxy-(6-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-3-hydroxymethyl-dihydro-furan-2-one