Hexacosanamide, N-[(1S,2S,3R)-2,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[[[2,3,4,6-tetrakis-O-(phenylmethyl)-alpha-D-galactopyranosyl]oxy]methyl]heptadecyl]-

Base Information

• Chemical Name: Hexacosanamide, N-[(1S,2S,3R)-2,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[[[2,3,4,6-tetrakis-O-(phenylmethyl)-alpha-D-galactopyranosyl]oxy]methyl]heptadecyl]-
• CAS No.: 205371-69-3
• Molecular Formula: C90H151NO9Si2
• Molecular Weight: 1447.36
• DSSTox Substance ID: DTXSID701099861
• Nikkaji Number: J2.045.884D
• Mol file: 205371-69-3.mol

Synonyms:205371-69-3;Hexacosanamide, N-[(1S,2S,3R)-2,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[[[2,3,4,6-tetrakis-O-(phenylmethyl)-alpha-D-galactopyranosyl]oxy]methyl]heptadecyl]-;DTXSID701099861;N-[(1S,2S,3R)-1-[(2-O,3-O,4-O,6-O-Tetrabenzyl-alpha-D-galactopyranosyloxy)methyl]-2,3-bis(tert-butyldimethylsilyloxy)heptadecyl]hexacosanamide;N-[(1S,2S,3R)-2,3-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[[[2,3,4,6-tetrakis-O-(phenylmethyl)-alpha-D-galactopyranosyl]oxy]methyl]heptadecyl]hexacosanamide

Chemical Property of Hexacosanamide, N-[(1S,2S,3R)-2,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[[[2,3,4,6-tetrakis-O-(phenylmethyl)-alpha-D-galactopyranosyl]oxy]methyl]heptadecyl]-

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1131.918°C at 760 mmHg
• Flash Point: 638.361°C
• PSA: 102.94000
• Density: 1.01g/cm³
• LogP: 25.83090
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 62
• Exact Mass: 1446.09273846
• Heavy Atom Count: 102
• Complexity: 1970

Purity/Quality:

98%Min ^*data from raw suppliers

1-(2,3,4,6-Tetrakis-O-benzyl)-2,3-bis(tert-butyldimethylsilyloxy)KRN7000 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)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]1[C@@H]([C@H]([C@H]([C@H](O1)COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)[C@@H]([C@@H](CCCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C
• Uses: Intermediate for the preparation of KRN7000.

Technology Process of Hexacosanamide, N-[(1S,2S,3R)-2,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[[[2,3,4,6-tetrakis-O-(phenylmethyl)-alpha-D-galactopyranosyl]oxy]methyl]heptadecyl]-

There total 3 articles about Hexacosanamide, N-[(1S,2S,3R)-2,3-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[[[2,3,4,6-tetrakis-O-(phenylmethyl)-alpha-D-galactopyranosyl]oxy]methyl]heptadecyl]- 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: 63.0%

2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetimidate (90358-01-3) + (2S,3S,4R)-3,4-di-O-tertbutyldimethylsilyl-2-(N-hexacosanoylamino)octadecan-1,3,4-triol (205371-68-2) → (2S,3S,4R)-3,4-bis-tert-butyldimethylsilyloxy-2-hexacosanoylamino-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecane (205371-69-3)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; at -20 ℃; for 3h;

DOI:10.1055/s-2004-822315

Reference yield: 53.0%

2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl fluoride (78153-79-4,89025-46-7,94898-42-7,101966-50-1,122741-44-0,143615-35-4,94898-43-8) + (2S,3S,4R)-3,4-di-O-tertbutyldimethylsilyl-2-(N-hexacosanoylamino)octadecan-1,3,4-triol (205371-68-2) → (2S,3S,4R)-3,4-bis-tert-butyldimethylsilyloxy-2-hexacosanoylamino-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecane (205371-69-3)

Guidance literature:

With 4 A molecular sieve; silver perchlorate; tin(ll) chloride; In tetrahydrofuran; at -10 - 20 ℃; for 2h;

DOI:10.1016/S0040-4020(98)00065-9

Reference yield:

2,3,4,6-tetra-O-benzyl-D-galactopyranosyl fluoride (143615-35-4) + (2S,3S,4R)-3,4-di-O-tertbutyldimethylsilyl-2-(N-hexacosanoylamino)octadecan-1,3,4-triol (205371-68-2) → (2S,3S,4R)-3,4-bis-tert-butyldimethylsilyloxy-2-hexacosanoylamino-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecane (205371-69-3) + (2S,3S,4R)-3,4-bis-tert-butyldimethylsilyloxy-2-hexacosanoylamino-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)octadecane

Guidance literature:

With silver perchlorate; tin(ll) chloride; In tetrahydrofuran; Title compound not separated from byproducts;

DOI:10.1055/s-2004-822315

upstream raw materials:

2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl fluoride

(2S,3S,4R)-3,4-di-O-tertbutyldimethylsilyl-2-(N-hexacosanoylamino)octadecan-1,3,4-triol

2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetimidate

2,3,4,6-tetra-O-benzyl-D-galactopyranosyl fluoride