Gomisin K2, (+)-

Base Information

• Chemical Name: Gomisin K2, (+)-
• CAS No.: 75684-44-5
• Molecular Formula: C₂₃H₃₀O₆
• Molecular Weight: 402.488
• UNII: D445L37O09,111FHP5Z80
• Wikidata: Q105233861
• Mol file: 75684-44-5.mol

Synonyms:Gomisin K2, (+)-;Gomisin K2;75629-20-8;(+)-Gomisin K2;(-)-Gomisin K1;Gomisin K1, (-)-;UNII-111FHP5Z80;UNII-D445L37O09;111FHP5Z80;D445L37O09;(9S,10R)-3,4,14,15,16-pentamethoxy-9,10-dimethyltricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaen-5-ol;75684-44-5;Dibenzo(a,C)cycloocten-3-ol, 5,6,7,8-tetrahydro-1,2,10,11,12-pentamethoxy-6,7-dimethyl-, (6S,7R,12aR)-;Dibenzo(a,C)cycloocten-3-ol, 5,6,7,8-tetrahydro-1,2,10,11,12-pentamethoxy-6,7-dimethyl-, (6S,7R,12aS)-;SCHEMBL5304084;(6S,7R,12AR)-5,6,7,8-TETRAHYDRO-1,2,10,11,12-PENTAMETHOXY-6,7-DIMETHYLDIBENZO(A,C)CYCLOOCTEN-3-OL;(6S,7R,12AS)-5,6,7,8-TETRAHYDRO-1,2,10,11,12-PENTAMETHOXY-6,7-DIMETHYLDIBENZO(A,C)CYCLOOCTEN-3-OL

Chemical Property of Gomisin K2, (+)-

Chemical Property:

• PSA: 66.38000
• LogP: 4.47300
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 402.20423867
• Heavy Atom Count: 29
• Complexity: 516

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CC2=CC(=C(C(=C2C3=C(C(=C(C=C3CC1C)OC)OC)OC)OC)OC)O
• Isomeric SMILES: C[C@H]1CC2=CC(=C(C(=C2C3=C(C(=C(C=C3C[C@H]1C)OC)OC)OC)OC)OC)O

Technology Process of Gomisin K2, (+)-

There total 12 articles about Gomisin K2, (+)- 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:

schisandrin A (156769-17-4) → (P*,6R*,7S*)-5,6,7,8-tetrahydro-6,7-dimethyl-2-hydroxy-1,3,10,11,12-pentamethoxy-dibenzocyclooctene + (6R,7S)-1,2,10,11,12-Pentamethoxy-6,7-dimethyl-5,6,7,8-tetrahydro-dibenzo[a,c]cycloocten-3-ol (75629-20-8,75684-44-5,110454-79-0) + 6(SR),7(RS)-5,6,7,8-tetrahydro-7-hydroxy-1,2,3,10,11,12-hexamethoxy-6,7-dimethyldibenzocyclooctene (7432-28-2,7488-47-3,68225-19-4,114422-18-3,130695-97-5,130695-99-7,130696-00-3,130696-01-4,135095-48-6,150197-51-6)

Guidance literature:

rat liver S₉ mix;

DOI:10.1248/cpb.42.1694

Reference yield:

(+/-)-4-(3,4,5-trimethoxyphenyl)-4,5-dihydro-2(3H)-furanone (65171-10-0) → (6R,7S)-1,2,10,11,12-Pentamethoxy-6,7-dimethyl-5,6,7,8-tetrahydro-dibenzo[a,c]cycloocten-3-ol (75629-20-8,75684-44-5,110454-79-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 63 percent / NaH, MeOH / toluene / 0.5 h / 20 °C

2: 96 percent / H₂ / Pd-C / acetic acid / 4 h

3: 95 percent / RuO₂-TFA-TFAA-BF₃OEt₂ / CH₂Cl₂ / 24 h / 20 °C

4: Ca(BH₄)2 / ethanol; H₂O / 0.33 h / 30 °C

5: pyridine / 0.25 h / 0 °C

6: lithium triethylborohydride / tetrahydrofuran / 0 deg C, 1h, reflux 2h

With methanol; ruthenium(IV) oxide; calcium borohydride; boron trifluoride diethyl etherate; hydrogen; sodium hydride; lithium triethylborohydride; trifluoroacetic acid; trifluoroacetic anhydride; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; dichloromethane; water; acetic acid; toluene;

DOI:10.1016/S0040-4039(00)85215-6

Reference yield:

(E)-3-benzyl-2-benzylidene-4-butanolide → (6R,7S)-1,2,10,11,12-Pentamethoxy-6,7-dimethyl-5,6,7,8-tetrahydro-dibenzo[a,c]cycloocten-3-ol (75629-20-8,75684-44-5,110454-79-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / H₂ / Pd-C / acetic acid / 4 h

2: 95 percent / RuO₂-TFA-TFAA-BF₃OEt₂ / CH₂Cl₂ / 24 h / 20 °C

3: Ca(BH₄)2 / ethanol; H₂O / 0.33 h / 30 °C

4: pyridine / 0.25 h / 0 °C

5: lithium triethylborohydride / tetrahydrofuran / 0 deg C, 1h, reflux 2h

With ruthenium(IV) oxide; calcium borohydride; boron trifluoride diethyl etherate; hydrogen; lithium triethylborohydride; trifluoroacetic acid; trifluoroacetic anhydride; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; dichloromethane; water; acetic acid;

DOI:10.1016/S0040-4039(00)85215-6

upstream raw materials:

Methanesulfonic acid (6S,7R)-7-methanesulfonyloxymethyl-1,2,3,10,11,12-hexamethoxy-5,6,7,8-tetrahydro-dibenzo[a,c]cycloocten-6-ylmethyl ester

schisandrin A

(+/-)-4-(3,4,5-trimethoxyphenyl)-4,5-dihydro-2(3H)-furanone

<(butanolidyl-4)-3 methyl>-6 formyl-6' hexamethoxy-2,3,4,2',3',4' biphenyle

Refernces

• 1、 Landais, Y.,Lebrun, A.,Robin, J. P.. "RUTHENIUM(IV) TETRAKIS(TRIFLUOROACETATE), A NEW OXIDIZING AGENT. II. A NEW ACCESS TO SCHIZANDRINS SKELETON USING BIARYL OXIDATIVE COUPLING OF CIS-SUBSTITUTED BUTANOLIDES". . p. 5377 - 5380. Retrieved 2007/10/02.