(4R,5S)-N-Benzyl-4-(t-butyldimethylsilyloxymethyl)-4-hydroxymethyl-5-isopropyloxazoladine

Base Information

• Chemical Name: (4R,5S)-N-Benzyl-4-(t-butyldimethylsilyloxymethyl)-4-hydroxymethyl-5-isopropyloxazoladine
• CAS No.: 145452-01-3
• Molecular Formula: C21H37NO3Si
• Molecular Weight: 379.60900
• DSSTox Substance ID: DTXSID00471256
• Wikidata: Q82299726
• Mol file: 145452-01-3.mol

Synonyms:145452-01-3;(4R,5S)-N-Benzyl-4-(t-butyldimethylsilyloxymethyl)-4-hydroxymethyl-5-isopropyloxazoladine;[(4R,5S)-3-benzyl-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-propan-2-yl-1,3-oxazolidin-4-yl]methanol;4-Oxazolidinemethanol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-5-(1-methylethyl)-3-(phenylmethyl)-, (4R-cis)- (9CI);DTXSID00471256;AKOS030241537;J-008110

Chemical Property of (4R,5S)-N-Benzyl-4-(t-butyldimethylsilyloxymethyl)-4-hydroxymethyl-5-isopropyloxazoladine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 446.148oC at 760 mmHg
• Flash Point: 223.623oC
• PSA: 41.93000
• Density: 0.998g/cm3
• LogP: 4.19170
• Solubility.: Acetone, Chloroform, Dichloromethane, Ethanol, Methanol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 379.25427058
• Heavy Atom Count: 26
• Complexity: 443

Purity/Quality:

97% ^*data from raw suppliers

(4R,5S)-N-Benzyl-4-(t-butyldimethylsilyloxymethyl)-4-hydroxymethyl-5-isopropyloxazoladine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1C(N(CO1)CC2=CC=CC=C2)(CO)CO[Si](C)(C)C(C)(C)C
• Isomeric SMILES: CC(C)[C@H]1[C@@](N(CO1)CC2=CC=CC=C2)(CO)CO[Si](C)(C)C(C)(C)C

Technology Process of (4R,5S)-N-Benzyl-4-(t-butyldimethylsilyloxymethyl)-4-hydroxymethyl-5-isopropyloxazoladine

There total 8 articles about (4R,5S)-N-Benzyl-4-(t-butyldimethylsilyloxymethyl)-4-hydroxymethyl-5-isopropyloxazoladine 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:

(4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidine-4-carboxylic acid methyl ester (145451-93-0) → [(4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-methanol (145452-01-3)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; methanol; at 23 ℃; for 24h;

DOI:10.1021/ja00052a096

Reference yield:

(2R,4R)-3-Benzyl-2-tert-butyl-4-((S)-1-hydroxy-2-methyl-propyl)-oxazolidine-4-carboxylic acid methyl ester (145451-90-7) → [(4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-methanol (145452-01-3)

Guidance literature:

Multi-step reaction with 4 steps

1: trifluoromethanesulfonic acid / methanol; H₂O / 6.5 h / 80 - 85 °C

2: imidazole / dimethylformamide / 25 h / 23 °C

3: p-TsOH*H₂O / benzene / 0.5 h / 80 °C

4: LiBH₄ / tetrahydrofuran; methanol / 20 h / 23 °C

With 1H-imidazole; lithium borohydride; trifluorormethanesulfonic acid; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja973444c

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → [(4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-methanol (145452-01-3)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / dimethylformamide / 25 h / 23 °C

2: p-TsOH*H₂O / benzene / 0.5 h / 80 °C

3: LiBH₄ / tetrahydrofuran; methanol / 20 h / 23 °C

With 1H-imidazole; lithium borohydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja973444c

upstream raw materials:

(4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidine-4-carboxylic acid methyl ester

tert-butyldimethylsilyl chloride

(2R,4R)-3-Benzyl-2-tert-butyl-4-((S)-1-hydroxy-2-methyl-propyl)-oxazolidine-4-carboxylic acid methyl ester

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

Downstream raw materials:

(4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidine-4-carbaldehyde

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

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

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

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