alpha-Multistriatin

Base Information

• Chemical Name: alpha-Multistriatin
• CAS No.: 54815-06-4
• Molecular Formula: C10H18O2
• Molecular Weight: 170.25
• Hs Code.: 2932999099
• UNII: MG6CJY1237,CCJ8A99MHA
• DSSTox Substance ID: DTXSID00897215
• Metabolomics Workbench ID: 144271
• Nikkaji Number: J14.694C
• Wikidata: Q27275399
• Wikipedia: Multistriatin
• Mol file: 54815-06-4.mol

Synonyms:multistriatin

Chemical Property of alpha-Multistriatin

Chemical Property:

• Vapor Pressure: 0.33mmHg at 25°C
• Boiling Point: 207.1°C at 760 mmHg
• Flash Point: 74.9°C
• PSA: 18.46000
• Density: 0.959g/cm³
• LogP: 2.18400
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 170.130679813
• Heavy Atom Count: 12
• Complexity: 181

Purity/Quality:

MULTISTRIATIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC12C(CC(C(O1)CO2)C)C
• Isomeric SMILES: CC[C@]12[C@H](C[C@H]([C@H](O1)CO2)C)C

Technology Process of alpha-Multistriatin

There total 55 articles about alpha-Multistriatin 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: 48.0%

(2R,3S,5R)-5-(2-Ethyl-[1,3]dioxolan-2-yl)-2-hydroxy-3-methyl-hexanal (85576-81-4) → α-multistriatin (54815-06-4)

Guidance literature:

With sodium cyanoborohydride; In tetrahydrofuran; water; pH 2-3;

DOI:10.1016/S0040-4039(00)85555-0

Reference yield:

(+/-)-r-2-Acetyl-c-4-formyl<1,3>dioxolane → δ-Multistriatin (54815-06-4,54832-20-1,54832-21-2,54832-22-3,59014-03-8,59014-04-9,59014-05-0,59014-06-1,59014-07-2,59014-08-3,59014-09-4,59014-10-7,60018-96-4)

Guidance literature:

Multi-step reaction with 7 steps

1: triethylammonium chloride / CH₂Cl₂ / 48 h / Ambient temperature

2: Et₃N, DMAP / 1.5 h / -5 °C

3: 180 - 200 °C

4: 1.) CuBr*Me₂S / 1.) ether, -60 to -30 deg C, 20 min, 2.) -60 deg C, 15 min

5: 76 percent / t-BuOK / 1.) THF, 6 h, 2.) ether, overnight

6: H₂ / Pd/C

7: TFA / 48 h

With dmap; copper(I) bromide dimethylsulfide complex; potassium tert-butylate; hydrogen; triethylamine; palladium on activated charcoal; triethylamine hydrochloride; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo00121a034

Reference yield:

(+/-)-1-<(2Ξ)-2-Ethyl-c-4-(hydroxymethyl)<1,3>dioxolan-r-2-yl>ethanol → δ-Multistriatin (54815-06-4,54832-20-1,54832-21-2,54832-22-3,59014-03-8,59014-04-9,59014-05-0,59014-06-1,59014-07-2,59014-08-3,59014-09-4,59014-10-7,60018-96-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) -40 deg C, 5 min

2: triethylammonium chloride / CH₂Cl₂ / 48 h / Ambient temperature

3: Et₃N, DMAP / 1.5 h / -5 °C

4: 180 - 200 °C

5: 1.) CuBr*Me₂S / 1.) ether, -60 to -30 deg C, 20 min, 2.) -60 deg C, 15 min

6: 76 percent / t-BuOK / 1.) THF, 6 h, 2.) ether, overnight

7: H₂ / Pd/C

8: TFA / 48 h

With dmap; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; potassium tert-butylate; hydrogen; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; triethylamine hydrochloride; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo00121a034

upstream raw materials:

N-(1-Ethyl-1-propenyl)cyclohexylamin

Toluene-4-sulfonic acid (S)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propyl ester

(2R,3S,5R)-5-(2-Ethyl-[1,3]dioxolan-2-yl)-2-hydroxy-3-methyl-hexanal

(2R,3S,5R)-2-Hydroxy-3,5-dimethyl-6-oxo-octanal

Downstream raw materials:

δ-Multistriatin

Refernces

• 1、 Mori, Yuji,Inaba, Mitsutoshi,Suzuki, Makuto. "DIELS-ALDER REACTIONS OF (1E),(3E)-2-METHYL-1-TRIMETHYLSILYLOXY-1,3-PENTADIENE AND THE SYNTHESIS OF MULTISTRIATINS FROM THE ADDUCTS". . p. 3488 - 3491. Retrieved 2007/10/02.
• 2、 Walba, David M.,Wand, Michael D.. "STEREOCONTROLLED SYNTHESIS OF SUBSTITUTED 2-ALKOXYTETRAHYDROPYRANS FROM MESO-2,4-DIMETHYLGLUTARIC ANHYDRIDE". . p. 4995 - 4998. Retrieved 2007/10/02.