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

Base Information

• Chemical Name: octyl 4-O-acetyl-2,3-di-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside
• CAS No.: 283587-73-5
• Molecular Formula: C₅₇H₇₀O₁₁
• Molecular Weight: 931.176
• Mol file: 283587-73-5.mol

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

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

There total 9 articles about octyl 4-O-acetyl-2,3-di-O-benzyl-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: 71.0%

octyl 3,4,6-tri-O-benzyl-β-D-galactopyranoside (220911-76-2) + ethyl 4-O-acetyl-2,3-di-O-benzyl-1-deoxy-1-thio-β-L-fucopyranoside (138343-58-5) → octyl 4-O-acetyl-2,3-di-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside (283587-73-5)

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; for 4h;

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

Reference yield:

octanol (111-87-5) → octyl 4-O-acetyl-2,3-di-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside (283587-73-5)

Guidance literature:

Multi-step reaction with 3 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

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

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 4-O-acetyl-2,3-di-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside (283587-73-5)

Guidance literature:

Multi-step reaction with 7 steps

1: NaOMe / methanol

2: camphorsulfonic acid

3: 93 percent / NaH / dimethylformamide

4: 84 percent / AcOH / 70 °C

5: 500 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

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;

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

upstream raw materials:

octyl 3,4,6-tri-O-benzyl-β-D-galactopyranoside

ethyl 4-O-acetyl-2,3-di-O-benzyl-1-deoxy-1-thio-β-L-fucopyranoside

octanol

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

Downstream raw materials:

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

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

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

Thiocarbonic acid O-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl] ester O-pentafluorophenyl ester