8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-D-glycero-D-gulo-D-gluco-tridecopyranolactone

Base Information

• Chemical Name: 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-D-glycero-D-gulo-D-gluco-tridecopyranolactone
• CAS No.: 558481-00-8
• Molecular Formula: C₆₂H₆₄O₁₀
• Molecular Weight: 969.184
• Mol file: 558481-00-8.mol

Synonyms:8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-D-glycero-D-gulo-D-gluco-tridecopyranolactone

Chemical Property of 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-D-glycero-D-gulo-D-gluco-tridecopyranolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-D-glycero-D-gulo-D-gluco-tridecopyranolactone

There total 2 articles about 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-D-glycero-D-gulo-D-gluco-tridecopyranolactone 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:

(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-tetrahydro-pyran-2-ol → 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-D-glycero-D-gulo-D-gluco-tridecopyranolactone (558481-00-8)

Guidance literature:

With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/chem.200390148

Reference yield:

methyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α-D-glycero-D-gulo-D-gluco-tridecopyranoside (139242-12-9) → 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-D-glycero-D-gulo-D-gluco-tridecopyranolactone (558481-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. H₂SO₄ / acetic acid / 1.25 h / 100 °C

2: 363 mg / pyridinium chlorochromate; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

With 4 A molecular sieve; sulfuric acid; pyridinium chlorochromate; In dichloromethane; acetic acid;

DOI:10.1002/chem.200390148

Reference yield:

trimethylsilylacetylene (1066-54-2) + 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-D-glycero-D-gulo-D-gluco-tridecopyranolactone (558481-00-8) → (3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-trimethylsilanylethynyl-6-[2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-tetrahydro-pyran-2-ol

Guidance literature:

trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h;

With cerium(III) chloride; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-D-glycero-D-gulo-D-gluco-tridecopyranolactone; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Further stages.;

DOI:10.1002/chem.200390148

upstream raw materials:

methyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α-D-glycero-D-gulo-D-gluco-tridecopyranoside

Downstream raw materials:

3,7:10,14-dianhydro-4,5,6,11,12,13,15-hepta-O-benzyl-1,2,8,9-tetradeoxy-D-erythro-L-talo-D-gulo-pentadec-1-ynitol