(3R,4S,5R,6S)-1-Aza-4-hydroxy-5-formyl-6-isopropyl-3-methyl-7-oxabicycl[3.3.0]octan-2-one

Base Information

• Chemical Name: (3R,4S,5R,6S)-1-Aza-4-hydroxy-5-formyl-6-isopropyl-3-methyl-7-oxabicycl[3.3.0]octan-2-one
• CAS No.: 145452-03-5
• Molecular Formula: C11H17NO4
• Molecular Weight: 227.26
• DSSTox Substance ID: DTXSID601103922
• Mol file: 145452-03-5.mol

Synonyms:145452-03-5;(3R,4S,5R,6S)-1-Aza-4-hydroxy-5-formyl-6-isopropyl-3-methyl-7-oxabicycl[3.3.0]octan-2-one;(1S,6R,7S,7aS)-7-hydroxy-6-methyl-5-oxo-1-propan-2-yl-1,3,6,7-tetrahydropyrrolo[1,2-c][1,3]oxazole-7a-carbaldehyde;1H,3H-Pyrrolo[1,2-c]oxazole-7a(5H)-carboxaldehyde, dihydro-7-hydroxy-6-methyl-1-(1-methylethyl)-5-oxo-, [1S-(1alpha,6alpha,7alpha,7aalpha)]- (9CI);DTXSID601103922;J-008112;1H,3H-Pyrrolo[1,2-c]oxazole-7a(5H)-carboxaldehyde, dihydro-7-hydroxy-6-methyl-1-(1-methylethyl)-5-oxo-, [1S-(1alpha,6alpha,7alpha,7aalpha)]-

Chemical Property of (3R,4S,5R,6S)-1-Aza-4-hydroxy-5-formyl-6-isopropyl-3-methyl-7-oxabicycl[3.3.0]octan-2-one

Chemical Property:

• Melting Point: 108-110°C
• Boiling Point: 402.0±45.0 °C(Predicted)
• PKA: 12.77±0.70(Predicted)
• PSA: 66.84000
• Density: 1.25±0.1 g/cm3(Predicted)
• LogP: -0.28650
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 227.11575802
• Heavy Atom Count: 16
• Complexity: 330

Purity/Quality:

98%Min ^*data from raw suppliers

(3R,4S,5R,6S)-1-Aza-4-hydroxy-5-formyl-6-isopropyl-3-methyl-7-oxabicycl[3.3.0]octan-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C2(C(OCN2C1=O)C(C)C)C=O)O
• Isomeric SMILES: C[C@@H]1[C@@H]([C@]2([C@@H](OCN2C1=O)C(C)C)C=O)O

Technology Process of (3R,4S,5R,6S)-1-Aza-4-hydroxy-5-formyl-6-isopropyl-3-methyl-7-oxabicycl[3.3.0]octan-2-one

There total 10 articles about (3R,4S,5R,6S)-1-Aza-4-hydroxy-5-formyl-6-isopropyl-3-methyl-7-oxabicycl[3.3.0]octan-2-one 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: 73.0%

(1S,6R,7S,7aS)-7-Hydroxy-7a-hydroxymethyl-1-isopropyl-6-methyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one (145452-02-4) → (1S,6R,7S,7aS)-7-Hydroxy-1-isopropyl-6-methyl-5-oxo-dihydro-pyrrolo[1,2-c]oxazole-7a-carbaldehyde (145452-03-5)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1021/ja00052a096

Reference yield:

(2R,3S)-3-[(4S,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-3-hydroxy-2-methyl-propionic acid methyl ester (203934-88-7) → (1S,6R,7S,7aS)-7-Hydroxy-1-isopropyl-6-methyl-5-oxo-dihydro-pyrrolo[1,2-c]oxazole-7a-carbaldehyde (145452-03-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) i-Pr₂NEt, H₂ / 1.) 10percent Pd/C / 1.) EtOH, 23 deg C, 22 h, 2.) MeOH, 50 deg C, 24 h

2: 48percent HF / acetonitrile / 24 h / 23 °C

3: Et₃N, oxalyl chloride, DMSO / CH₂Cl₂ / 2 h / -78 °C

With oxalyl dichloride; hydrogen fluoride; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In dichloromethane; acetonitrile;

DOI:10.1021/ja973444c

Reference yield:

(2R,3S)-2-Benzylamino-3-hydroxy-2-hydroxymethyl-4-methyl-pentanoic acid methyl ester (145451-91-8) → (1S,6R,7S,7aS)-7-Hydroxy-1-isopropyl-6-methyl-5-oxo-dihydro-pyrrolo[1,2-c]oxazole-7a-carbaldehyde (145452-03-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 97 percent / imidazole / dimethylformamide / 3.5 h / 23 °C

2: 96 percent / TsOH / benzene / 0.5 h / Heating

3: LiBH₄ / tetrahydrofuran; methanol / 24 h / 23 °C

4: DMSO, (COCl)2, Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

5: 1.) LDA / 1.) THF, -78 deg C

6: 87 percent / H₂ / Pd/C / ethanol / 24 h / 23 °C

7: 90 percent / 5percent HF / acetonitrile / 9 h / 23 °C

8: 73 percent / DMSO, (COCl)2, Et₃N / CH₂Cl₂ / 2 h / -78 °C

With 1H-imidazole; lithium borohydride; oxalyl dichloride; hydrogen fluoride; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/ja00052a096

upstream raw materials:

(1S,6R,7S,7aS)-7-Hydroxy-7a-hydroxymethyl-1-isopropyl-6-methyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

(1S,6R,7S,7aS)-7a-(tert-Butyl-dimethyl-silanyloxymethyl)-7-hydroxy-1-isopropyl-6-methyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

(2R,3S)-3-[(4S,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-3-hydroxy-2-methyl-propionic acid methyl ester

(2R,3S)-2-Benzylamino-3-hydroxy-2-hydroxymethyl-4-methyl-pentanoic acid methyl ester

Downstream raw materials:

(1S,6R,7S,7aS)-7-Hydroxy-1-isopropyl-6-methyl-5-oxo-dihydro-pyrrolo[1,2-c]oxazole-7a-carboxylic acid

(3R,4S,5R,1'S)-4-hydroxy-5-(1'-hydroxy-2'-methylpropyl)-3-methylpyrrolidin-2-one-5-carboxylic acid

Lactacystin

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