octyl 2,4-di-O-benzyl-3-O-methyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside

Base Information

• Chemical Name: octyl 2,4-di-O-benzyl-3-O-methyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside
• CAS No.: 283587-80-4
• Molecular Formula: C₅₆H₇₀O₁₀
• Molecular Weight: 903.166
• Mol file: 283587-80-4.mol

Synonyms:octyl 2,4-di-O-benzyl-3-O-methyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside

Chemical Property of octyl 2,4-di-O-benzyl-3-O-methyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of octyl 2,4-di-O-benzyl-3-O-methyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside

There total 12 articles about octyl 2,4-di-O-benzyl-3-O-methyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside 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: 86.0%

octyl 2,4-di-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside (283587-79-1) + methyl iodide (74-88-4) → octyl 2,4-di-O-benzyl-3-O-methyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside (283587-80-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)00003-3

Reference yield:

octanol (111-87-5) → octyl 2,4-di-O-benzyl-3-O-methyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside (283587-80-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 74 percent / Hg(CN)2; molecular sieves 3 Angstroem; HgBr₂ / acetonitrile

2: 97 percent / NaOMe / methanol

3: 71 percent / DMTST; DTBMP; 4 Angstroem molecular sieves / CH₂Cl₂ / 4 h

4: 92 percent / NaOMe / methanol

5: 86 percent / NaH / dimethylformamide

With 2,6-di-tert-butyl-4-methylpyridine; 3 A molecular sieve; 4 A molecular sieve; sodium methylate; mercury(II) cyanide; sodium hydride; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; mercury dibromide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Glycosylation / 2: Deacetylation / 3: Glycosylation / 4: Deacetylation / 5: Methylation;

DOI:10.1016/S0008-6215(00)00003-3

Reference yield:

ethyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside (127501-41-1) → octyl 2,4-di-O-benzyl-3-O-methyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside (283587-80-4)

Guidance literature:

Multi-step reaction with 9 steps

1: NaOMe / methanol

2: camphorsulfonic acid

3: 93 percent / NaH / dimethylformamide

4: 84 percent / AcOH / 70 °C

5: 600 mg / Bu₄NHSO₄; NaOH / CH₂Cl₂; H₂O / 48 h / 20 °C

6: 89 percent / pyridine

7: 71 percent / DMTST; DTBMP; 4 Angstroem molecular sieves / CH₂Cl₂ / 4 h

8: 92 percent / NaOMe / methanol

9: 86 percent / NaH / dimethylformamide

With pyridine; sodium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; acetic acid; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In methanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Deacetylation / 2: Cyclization / 3: Alkylation / 4: Hydrolysis / 5: Alkylation / 6: Acetylation / 7: Glycosylation / 8: Deacetylation / 9: Methylation;

DOI:10.1016/S0008-6215(00)00003-3

upstream raw materials:

octyl 2,4-di-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside

methyl iodide

octanol

ethyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside