Isoyatein

Base Information

• Chemical Name: Isoyatein
• CAS No.: 101751-72-8
• Molecular Formula: C22H24O7
• Molecular Weight: 400.42
• DSSTox Substance ID: DTXSID901117429
• Nikkaji Number: J2.538.697C
• Wikidata: Q105028515
• Mol file: 101751-72-8.mol

Synonyms:Isoyatein;CHEBI:175196;DTXSID901117429;(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one;(3R,4R)-3-(1,3-Benzodioxol-5-ylmethyl)dihydro-4-[(3,4,5-trimethoxyphenyl)methyl]-2(3H)-furanone;101751-72-8

Chemical Property of Isoyatein

Chemical Property:

• PSA: 72.45000
• LogP: 3.01550
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 400.15220310
• Heavy Atom Count: 29
• Complexity: 541

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)CC2COC(=O)C2CC3=CC4=C(C=C3)OCO4
• Isomeric SMILES: COC1=CC(=CC(=C1OC)OC)C[C@H]2COC(=O)[C@@H]2CC3=CC4=C(C=C3)OCO4

Technology Process of Isoyatein

There total 37 articles about Isoyatein 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:

C22H26O7 → trans-α-(3,4-methylenedioxybenzyl)-β-(3,4,5-trimethoxybenzyl)-γ-butyrolactone (101751-72-8,131351-72-9,131351-73-0)

Guidance literature:

With Fetizon's reagent; In toluene; for 3h; Inert atmosphere; Reflux;

DOI:10.3390/molecules23123057

Reference yield:

3,4,5-trimethoxy-benzaldehyde (86-81-7) → trans-α-(3,4-methylenedioxybenzyl)-β-(3,4,5-trimethoxybenzyl)-γ-butyrolactone (101751-72-8,131351-72-9,131351-73-0)

Guidance literature:

Multi-step reaction with 7 steps

1: t-BuOH / 2-methyl-propan-2-ol / 0.5 h / 40 °C

2: H₂ / 10percent Pd/C / methanol / 6 h / 760 Torr

3: 1.) t-BuOK, 2.) NaBH₄, CaCl₂ / 1.) EtOH, 2.) EtOH, RT, 12 h

4: 1.) LDA / 1.) hexane, THF, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 1 h

5: Et₃N, 4-(dimethylamino)pyridine / tetrahydrofuran / 5 h / Ambient temperature

6: NaH / tetrahydrofuran / 12 h / Ambient temperature

7: NaBH₄, NiCl₂*6H₂O / methanol; tetrahydrofuran / 1 h / 0 °C

With dmap; sodium tetrahydroborate; potassium tert-butylate; hydrogen; sodium hydride; triethylamine; calcium chloride; nickel dichloride; tert-butyl alcohol; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; tert-butyl alcohol;

DOI:10.1246/bcsj.69.2281

Reference yield:

2-methoxy-4-[1-(3,4,5-trimethoxyphenyl)-meth-(Z)-ylidene]-dihydrofuran-3,3-dicarboxylic acid dimethyl ester (862785-22-6) → cis-α-(3,4-methylenedioxybenzyl)-β-(3,4,5-trimethoxybenzyl)-γ-butyrolactone (101751-72-8,131351-72-9,131351-73-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 99 percent / H₂ / Pd/C / ethyl acetate / 7500.6 Torr

2.1: 89 percent / Yb(OTf)3 / methanol / Heating

3.1: K₂CO₃ / dimethylformamide / 20 °C

3.2: LiCl / dimethylformamide / 4 h / 130 °C

With hydrogen; potassium carbonate; ytterbium(III) triflate; palladium on activated charcoal; In methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ol050690h

upstream raw materials:

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

piperonal

2-methoxy-4-[1-(3,4,5-trimethoxyphenyl)-meth-(Z)-ylidene]-dihydrofuran-3,3-dicarboxylic acid dimethyl ester

5-iodo-1,2,3-trimethoxybenzene

Downstream raw materials:

(-)-Dihydroclusin

C₂₂H₂₃⁽²⁾HO₇

C₂₂H₂₃⁽²⁾HO₇

(3R,4S)-3-Benzo[1,3]dioxol-5-ylmethyl-3-hydroxy-4-(3,4,5-trimethoxy-benzyl)-dihydro-furan-2-one

Refernces

• 1、 Ferrie, Laurent,Bouyssi, Didier,Balme, Genevieve. "Selective Lewis acid catalyzed transformation (γ-butyrolactone versus cyclopropane) of 2-methoxy-4-benzyltetrahydrofuran derivatives. Efficient synthesis of lignan lactones". . p. 3143 - 3146. Retrieved 2007/10/03.
• 2、 Moritani, Yasunori,Fukushima, Chiaki,Ukita, Tatsuzo,Miyagishima, Toshikazu,Ohmizu, Hiroshi,Iwasaki, Tameo. "Stereoselective syntheses of cis- and trans-isomers of α-hydroxy-α,β-dibenzyl-γ-butyrolactone lignans: New syntheses of (±)-trachelogenin and (±)-guayadequiol". . p. 6922 - 6930. Retrieved 2007/10/03.