(2S,3R)-3-benzyloxy-2-(N-hexacosanoylamino)-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecane

Base Information

• Chemical Name: (2S,3R)-3-benzyloxy-2-(N-hexacosanoylamino)-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecane
• CAS No.: 872356-76-8
• Molecular Formula: C₈₅H₁₂₉NO₈
• Molecular Weight: 1292.96
• Mol file: 872356-76-8.mol

Synonyms:(2S,3R)-3-benzyloxy-2-(N-hexacosanoylamino)-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecane

Chemical Property of (2S,3R)-3-benzyloxy-2-(N-hexacosanoylamino)-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-benzyloxy-2-(N-hexacosanoylamino)-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecane

There total 10 articles about (2S,3R)-3-benzyloxy-2-(N-hexacosanoylamino)-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecane 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: 26.0%

(2S,3R)-3-O-benzyl-2-(N-hexacosanoylamino)octadecan-1,3-diol (872356-75-7) + 2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-galactopyranosyl fluoride (101966-50-1) → (2S,3R)-3-benzyloxy-2-(N-hexacosanoylamino)-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecane (872356-76-8)

Guidance literature:

With silver perchlorate; tin(ll) chloride; In tetrahydrofuran; at -10 - 20 ℃;

DOI:10.1021/jo051147h

Reference yield:

(2S)-2-(N-tert-butoxycarbonyl)amino-1-hydroxyoctadecan-3-one (437609-37-5) → (2S,3R)-3-benzyloxy-2-(N-hexacosanoylamino)-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecane (872356-76-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 83 percent / imidazole; 4-dimethylaminopyridine / dimethylformamide

2: 86 percent / LiAl(t-BuO)3H / ethanol / 6 h / -78 °C

3: 53 percent / NaH; tetrabutylammonium iodide / dimethylformamide / 0 - 20 °C

4: 93 percent / CF₃CO₂H; H₂O / 2 h

5: 70 percent / pyridine / 18 h

6: 26 percent / SnCl₂; AgClO₄ / tetrahydrofuran / -10 - 20 °C

With pyridine; 1H-imidazole; dmap; water; silver perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium tri-t-butoxyaluminum hydride; trifluoroacetic acid; tin(ll) chloride; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo051147h

Reference yield:

(2S,3R)-2-amino-3-benzyloxyoctadecan-1-ol (872356-72-4) → (2S,3R)-3-benzyloxy-2-(N-hexacosanoylamino)-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecane (872356-76-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / pyridine / 18 h

2: 26 percent / SnCl₂; AgClO₄ / tetrahydrofuran / -10 - 20 °C

With pyridine; silver perchlorate; tin(ll) chloride; In tetrahydrofuran;

DOI:10.1021/jo051147h

upstream raw materials:

(2S,3R)-3-O-benzyl-2-(N-hexacosanoylamino)octadecan-1,3-diol

2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-galactopyranosyl fluoride

(2S,3R)-2-amino-3-benzyloxyoctadecan-1-ol

(2S)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxyoctadecan-3-one