2,3-anhydro-4,6-O-benzylidene-D-glycero-α-D-manno-heptopyranoside

Base Information

• Chemical Name: 2,3-anhydro-4,6-O-benzylidene-D-glycero-α-D-manno-heptopyranoside
• CAS No.: 155021-01-5
• Molecular Formula: C₁₅H₁₈O₆
• Molecular Weight: 294.304
• Mol file: 155021-01-5.mol

Synonyms:2,3-anhydro-4,6-O-benzylidene-D-glycero-α-D-manno-heptopyranoside

Chemical Property of 2,3-anhydro-4,6-O-benzylidene-D-glycero-α-D-manno-heptopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-anhydro-4,6-O-benzylidene-D-glycero-α-D-manno-heptopyranoside

There total 8 articles about 2,3-anhydro-4,6-O-benzylidene-D-glycero-α-D-manno-heptopyranoside 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 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside (40653-15-4) → 2,3-anhydro-4,6-O-benzylidene-D-glycero-α-D-manno-heptopyranoside (155021-01-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 18 percent / CH₂Cl₂ / 1.) 0 deg C, overnight, 2.) RT, 3 h

2: 1.) CH₃I, 2.) NaBH₄, 3.) H₂O, HgCl₂, 4.) NaBH₄

3: H₂ / 5percent Pd/C / ethanol

4: 71 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

5: 76 percent / p-toluenesulfonic acid / toluene / 1 h / 30 °C

6: 1.) sodium hydride, tosyl imidazole / 1.) DMF, 30 min, 2.) DMF, RT, 84 h

With 1H-imidazole; sodium tetrahydroborate; water; hydrogen; sodium hydride; toluene-4-sulfonic acid; p-toluenesulfonyl imidazole; mercury dichloride; methyl iodide; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1139/v94-036

Reference yield:

methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside (34212-64-1,641635-63-4) → 2,3-anhydro-4,6-O-benzylidene-D-glycero-α-D-manno-heptopyranoside (155021-01-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) methyl sulfoxide, oxalyl chloride, 2.) ET₃N / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) CH₂Cl₂, from -60 deg C to RT

2: 18 percent / CH₂Cl₂ / 1.) 0 deg C, overnight, 2.) RT, 3 h

3: 1.) CH₃I, 2.) NaBH₄, 3.) H₂O, HgCl₂, 4.) NaBH₄

4: H₂ / 5percent Pd/C / ethanol

5: 71 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

6: 76 percent / p-toluenesulfonic acid / toluene / 1 h / 30 °C

7: 1.) sodium hydride, tosyl imidazole / 1.) DMF, 30 min, 2.) DMF, RT, 84 h

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; water; hydrogen; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; p-toluenesulfonyl imidazole; mercury dichloride; methyl iodide; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1139/v94-036

Reference yield:

methyl 2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside (103597-20-2) → 2,3-anhydro-4,6-O-benzylidene-D-glycero-α-D-manno-heptopyranoside (155021-01-5)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / 5percent Pd/C / ethanol

2: 71 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

3: 76 percent / p-toluenesulfonic acid / toluene / 1 h / 30 °C

4: 1.) sodium hydride, tosyl imidazole / 1.) DMF, 30 min, 2.) DMF, RT, 84 h

With 1H-imidazole; hydrogen; sodium hydride; toluene-4-sulfonic acid; p-toluenesulfonyl imidazole; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide; toluene;

DOI:10.1139/v94-036

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside

methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside

methyl 2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside

methyl D-glycero-α-D-gluco-heptopyranoside

Downstream raw materials:

methyl 4,6-O-benzylidene-3-O-methyl-D-glycero-α-D-altro-heptopyranoside

methyl 4,6-O-benzylidene-D-glycero-α-D-altro-heptopyranoside