alpha-Methylomuralide

Base Information

• Chemical Name: alpha-Methylomuralide
• CAS No.: 215232-00-1
• Molecular Formula: C₁₁H₁₇NO₄
• Molecular Weight: 227.26
• DSSTox Substance ID: DTXSID50441085
• Nikkaji Number: J985.911J
• Wikidata: Q82257664
• Mol file: 215232-00-1.mol

Synonyms:alpha-methylomuralide;methylomuralide

Chemical Property of alpha-Methylomuralide

Chemical Property:

• Melting Point: 181-183 °C
• Boiling Point: 428.9±40.0 °C(Predicted)
• PKA: 13.33±0.20(Predicted)
• PSA: 79.12000
• Density: 1.228±0.06 g/cm3(Predicted)
• LogP: 0.09940
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 227.11575802
• Heavy Atom Count: 16
• Complexity: 363

Purity/Quality:

97% ^*data from raw suppliers

α-MethylOmuralide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C12C(C(C(=O)N1)(C)C)OC2=O)O
• Isomeric SMILES: CC(C)[C@@H]([C@]12[C@H](C(C(=O)N1)(C)C)OC2=O)O
• Uses: Potent, selective, irreversible inhibitor of proteasome function. A cell permeable α-methyl analog of clasto-Lactacytin (C562500).

Technology Process of alpha-Methylomuralide

There total 21 articles about alpha-Methylomuralide 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: 90.0%

(2R,3S)-3-Hydroxy-2-((S)-1-hydroxy-2-methyl-propyl)-4,4-dimethyl-5-oxo-pyrrolidine-2-carboxylic acid (215232-04-5) → α-methylomuralide (215232-00-1)

Guidance literature:

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In dichloromethane; at 23 ℃; for 0.5h;

DOI:10.1016/S0040-4039(98)01674-8

Reference yield:

methyl (2E)-4-methylpent-2-enoate (20515-15-5) → α-methylomuralide (215232-00-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 92 percent / (DHQ)2PHAL; K₂OsO₂(OH)4; K₃[Fe(CN)6] / K₂CO₃; NaHCO₃ / 2-methyl-propan-2-ol; H₂O; various solvent(s) / 72 h / 5 °C

2.1: 100 percent / SOCl₂; pyridine / CH₂Cl₂ / cooling

3.1: 97 percent / NaIO₄; RuCl₃ / CCl₄; acetonitrile; H₂O / 1.5 h / 20 °C

4.1: 90 percent / NaN₃ / acetone; H₂O / 2 h / 20 °C

5.1: 99 percent / H₂ / Pd/C / ethanol; ethyl acetate / 24 h / 20 °C / 760 Torr

6.1: 85 percent / p-TsOH*H₂O / 1,2-dimethoxy-ethane / 4 h / Heating

7.1: 96 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 12 h / 20 °C

8.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

8.2: 81 percent / tetrahydrofuran; diethyl ether / 3 h / -78 °C

9.1: 99 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3 h / -78 °C

10.1: 67 percent / LiClO₄ / CH₂Cl₂ / 5 h / 0 °C

11.1: 89 percent / aq. HCl / methanol / 5 h / Heating

12.1: aq. NaOH / 40 h / 5 °C

With pyridine; hydrogenchloride; ruthenium trichloride; sodium hydroxide; sodium periodate; thionyl chloride; sodium azide; Hydroquinone 1,4-phthalazinediyl diether; oxalyl dichloride; potassium dioxotetrahydroxoosmate(VI); hydrogen; lithium perchlorate; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; potassium hexacyanoferrate(III); palladium on activated charcoal; sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran; methanol; tetrachloromethane; 1,2-dimethoxyethane; ethanol; dichloromethane; water; ethyl acetate; acetone; acetonitrile; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation / 9.1: Swern oxidation / 10.1: Mukaiyama aldol coupling;

DOI:10.1021/jo0268916

Reference yield:

(2R,3S)-2,3-dihydroxy-4-methylpentanoic acid methyl ester (220805-65-2) → α-methylomuralide (215232-00-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 100 percent / SOCl₂; pyridine / CH₂Cl₂ / cooling

2.1: 97 percent / NaIO₄; RuCl₃ / CCl₄; acetonitrile; H₂O / 1.5 h / 20 °C

3.1: 90 percent / NaN₃ / acetone; H₂O / 2 h / 20 °C

4.1: 99 percent / H₂ / Pd/C / ethanol; ethyl acetate / 24 h / 20 °C / 760 Torr

5.1: 85 percent / p-TsOH*H₂O / 1,2-dimethoxy-ethane / 4 h / Heating

6.1: 96 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 12 h / 20 °C

7.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

7.2: 81 percent / tetrahydrofuran; diethyl ether / 3 h / -78 °C

8.1: 99 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3 h / -78 °C

9.1: 67 percent / LiClO₄ / CH₂Cl₂ / 5 h / 0 °C

10.1: 89 percent / aq. HCl / methanol / 5 h / Heating

11.1: aq. NaOH / 40 h / 5 °C

With pyridine; hydrogenchloride; ruthenium trichloride; sodium hydroxide; sodium periodate; thionyl chloride; sodium azide; oxalyl dichloride; hydrogen; lithium perchlorate; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; 1,2-dimethoxyethane; ethanol; dichloromethane; water; ethyl acetate; acetone; acetonitrile; 8.1: Swern oxidation / 9.1: Mukaiyama aldol coupling;

DOI:10.1021/jo0268916

upstream raw materials:

(2R,3S)-3-Hydroxy-2-((S)-1-hydroxy-2-methyl-propyl)-4,4-dimethyl-5-oxo-pyrrolidine-2-carboxylic acid

methyl (2E)-4-methylpent-2-enoate

(2S,3S)-3-hydroxyleucine methyl ester

(4R,5S)-5-isopropyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester

Refernces

• 1、 Saravanan,Corey. "A short, stereocontrolled, and practical synthesis of α-methylomuralide, a potent inhibitor of proteasome function". . p. 2760 - 2764. Retrieved 2007/10/03.