1-O-acetyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α,β-D-glycero-D-gulo-D-gluco-tridecopyranose

Base Information

• Chemical Name: 1-O-acetyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α,β-D-glycero-D-gulo-D-gluco-tridecopyranose
• CAS No.: 405071-88-7
• Molecular Formula: C₆₄H₆₈O₁₁
• Molecular Weight: 1013.24
• Mol file: 405071-88-7.mol

Synonyms:1-O-acetyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α,β-D-glycero-D-gulo-D-gluco-tridecopyranose

Chemical Property of 1-O-acetyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α,β-D-glycero-D-gulo-D-gluco-tridecopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-acetyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α,β-D-glycero-D-gulo-D-gluco-tridecopyranose

There total 3 articles about 1-O-acetyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α,β-D-glycero-D-gulo-D-gluco-tridecopyranose 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:

methyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α-D-glycero-D-gulo-tridec-6-enopyranoside (252851-44-8) → 1-O-acetyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α,β-D-glycero-D-gulo-D-gluco-tridecopyranose (405071-88-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / TsNHNH₂; aq. AcONa / 1,2-dimethoxy-ethane / 1 h / 85 °C

2: aq. AcOH; H₂SO₄ / 1.25 h / 100 °C

3: 425 mg / pyridine / 3 h / 20 °C

With pyridine; sulfuric acid; sodium acetate; acetic acid; toluene-4-sulfonic acid hydrazide; In 1,2-dimethoxyethane;

DOI:10.1039/b106029p

Reference yield:

acetic anhydride (108-24-7) + (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 → 1-O-acetyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α,β-D-glycero-D-gulo-D-gluco-tridecopyranose (405071-88-7)

Guidance literature:

With pyridine; at 20 ℃; for 3h;

DOI:10.1039/b106029p

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) → 1-O-acetyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α,β-D-glycero-D-gulo-D-gluco-tridecopyranose (405071-88-7)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. AcOH; H₂SO₄ / 1.25 h / 100 °C

2: 425 mg / pyridine / 3 h / 20 °C

With pyridine; sulfuric acid; acetic acid;

DOI:10.1039/b106029p

upstream raw materials:

acetic anhydride

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

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

Downstream raw materials:

4,8:11,15-dianhydro-5,6,7,12,13,14,16-hepta-O-benzyl-1,2,3,9,10-pentadeoxy-D-erythro-L-talo-D-ido-hexadec-1-enitol