(2S,3S,4R)-3,4-Bis[(tert-butyldimethylsilyl)oxy]-2-hexacosanoylamino-4-octadecanol

Base Information

• Chemical Name: (2S,3S,4R)-3,4-Bis[(tert-butyldimethylsilyl)oxy]-2-hexacosanoylamino-4-octadecanol
• CAS No.: 205371-68-2
• Molecular Formula: C56H117NO4Si2
• Molecular Weight: 924.72
• DSSTox Substance ID: DTXSID80453277
• Nikkaji Number: J2.861.282F
• Wikidata: Q82274389
• Mol file: 205371-68-2.mol

Synonyms:205371-68-2;(2S,3S,4R)-3,4-BIS[(TERT-BUTYLDIMETHYLSILYL)OXY]-2-HEXACOSANOYLAMINO-4-OCTADECANOL;N-[(2S,3S,4R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-1-hydroxyoctadecan-2-yl]hexacosanamide;Hexacosanamide, N-[(1S,2S,3R)-2,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(hydroxymethyl)heptadecyl]-;-4-octadecanol;N-[(2S,3S,4R)-3,4-Bis{[tert-butyl(dimethyl)silyl]oxy}-1-hydroxyoctadecan-2-yl]hexacosanamide;SCHEMBL12632771;DTXSID80453277;MILYVWHUDKCSIS-JVDXJGRDSA-N;MFCD31720959;AKOS030241749;J-013388;N-Hexacosanoyl-3-O,4-O-bis(tert-butyldimethylsilyl)phytosphingosine;(2S,3S,4R)-3,4-Bis[(TBDMS)oxy]-2-hexacosanoylamino-4-octadecanol;(2S,3S,4R)-3,4-Bis[(tert-butyldimethylsilyl)oxy]-2-hexacosanoylamino;N-((2S,3S,4R)-3,4-Bis((tert-butyldimethylsilyl)oxy)-1-hydroxyoctadecan-2-yl)hexacosanamide

Chemical Property of (2S,3S,4R)-3,4-Bis[(tert-butyldimethylsilyl)oxy]-2-hexacosanoylamino-4-octadecanol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 839.375°C at 760 mmHg
• Flash Point: 461.437°C
• PSA: 71.28000
• Density: 0.888g/cm³
• LogP: 19.55810
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 47
• Exact Mass: 923.85211428
• Heavy Atom Count: 63
• Complexity: 1020

Purity/Quality:

98%Min ^*data from raw suppliers

(2S,3S,4R)-3,4-Bis[(tert-butyldimethylsilyl)oxy]-2-hexacosanoylamino-4-octadecanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)NC(CO)C(C(CCCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C
• Isomeric SMILES: CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H]([C@@H](CCCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C

Technology Process of (2S,3S,4R)-3,4-Bis[(tert-butyldimethylsilyl)oxy]-2-hexacosanoylamino-4-octadecanol

There total 23 articles about (2S,3S,4R)-3,4-Bis[(tert-butyldimethylsilyl)oxy]-2-hexacosanoylamino-4-octadecanol 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: 85.0%

(2S,3S,4R)-1,3,4-tris-tert-butyldimethylsilyloxy-2-hexacosanoylamino-4-octadecane (205371-67-1) → (2S,3S,4R)-3,4-di-O-tertbutyldimethylsilyl-2-(N-hexacosanoylamino)octadecan-1,3,4-triol (205371-68-2)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; at -10 - 10 ℃; for 2.5h;

DOI:10.1055/s-2004-822315

Reference yield: 82.0%

(2S,3S,4R)-1-benzyloxy-3,4-bis-(tert-butyldimethylsilyloxy)-2-hexacosanoylamino-octadecane (1388155-16-5) → (2S,3S,4R)-3,4-di-O-tertbutyldimethylsilyl-2-(N-hexacosanoylamino)octadecan-1,3,4-triol (205371-68-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; palladium(II) hydroxide; In methanol; at 20 ℃; for 12h;

DOI:10.1016/j.tet.2012.05.120

Reference yield:

1-hexacosanoic acid (506-46-7) → (2S,3S,4R)-3,4-di-O-tertbutyldimethylsilyl-2-(N-hexacosanoylamino)octadecan-1,3,4-triol (205371-68-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / EDCI / CH₂Cl₂ / 3 h / 40 °C

2: 95 percent / Et₃N / tetrahydrofuran / 14 h / 50 °C

3: 80 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 20 °C

4: 85 percent / aq. TFA / tetrahydrofuran / 2.5 h / -10 - 10 °C

With 2,6-dimethylpyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1055/s-2004-822315

upstream raw materials:

(2S,3S,4R)-1,3,4-tris-tert-butyldimethylsilyloxy-2-hexacosanoylamino-4-octadecane

hexacosanoic acid 2,5-dioxo-pyrrolidin-1-yl ester

1-hexacosanoic acid

hexacosanoic acid (2,3-dihydroxy-1-hydroxymethyl-heptadecyl) amide

Downstream raw materials:

Hexacosanoic acid [(1S,2S,3R)-1-((2S,3R,4S,5S,6R)-6-azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-heptadecyl]-amide

(2S,3S,4R)-2-(hexacosanamido)-1-O-(2,3,4-tri-O-benzyl-6-deoxy-6-fluoro-α-D-galactopyranosyl)octadecane-1,3,4-triol

(2S,3S,4R)-2-(hexacosanamido)-1-O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)octadecane-1,3,4-triol

(2S,3S,4R)-2-(hexacosanamido)-1-O-(2,3,4-tri-O-benzyl-6-deoxy-6-methyl-α-D-galactopyranosyl)octadecane-1,3,4-triol