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

Base Information

• Chemical Name: octyl 2,4-di-O-benzyl-α-L-xylo-hexopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside
• CAS No.: 283587-82-6
• Molecular Formula: C₅₅H₆₈O₉
• Molecular Weight: 873.14
• Mol file: 283587-82-6.mol

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

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

There total 13 articles about octyl 2,4-di-O-benzyl-α-L-xylo-hexopyranosyl-(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: 76.0%

Thiocarbonic acid O-[(2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-4-yl] ester O-pentafluorophenyl ester (283587-81-5) → octyl 2,4-di-O-benzyl-α-L-xylo-hexopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside (283587-82-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 130 ℃; for 4h;

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

Reference yield:

octanol (111-87-5) → octyl 2,4-di-O-benzyl-α-L-xylo-hexopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside (283587-82-6)

Guidance literature:

Multi-step reaction with 6 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: 98 percent / DMAP / CH₂Cl₂ / 14 h

6: 76 percent / Bu₃SnH; AIBN / toluene / 4 h / 130 °C

With dmap; 2,6-di-tert-butyl-4-methylpyridine; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; 4 A molecular sieve; tri-n-butyl-tin hydride; sodium methylate; mercury(II) cyanide; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; mercury dibromide; In methanol; dichloromethane; toluene; acetonitrile; 1: Glycosylation / 2: Deacetylation / 3: Glycosylation / 4: Deacetylation / 5: Acylation / 6: Barton's radical deoxygenation;

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-α-L-xylo-hexopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside (283587-82-6)

Guidance literature:

Multi-step reaction with 10 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: 98 percent / DMAP / CH₂Cl₂ / 14 h

10: 76 percent / Bu₃SnH; AIBN / toluene / 4 h / 130 °C

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

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

upstream raw materials:

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

octanol

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

ethyl 1-thio-α-L-fucopyranoside