(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-L-glycero-β-D-manno-heptopyranose

Base Information

• Chemical Name: (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-L-glycero-β-D-manno-heptopyranose
• CAS No.: 215381-20-7
• Molecular Formula: C₄₃H₄₀O₁₆
• Molecular Weight: 812.781
• Mol file: 215381-20-7.mol

Synonyms:(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-L-glycero-β-D-manno-heptopyranose

Chemical Property of (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-L-glycero-β-D-manno-heptopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-L-glycero-β-D-manno-heptopyranose

There total 15 articles about (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-L-glycero-β-D-manno-heptopyranose 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: 85.0%

(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-2,3-O-isopropylidene-L-glycero-β-D-manno-heptopyranose (215381-19-4) → (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-L-glycero-β-D-manno-heptopyranose (215381-20-7)

Guidance literature:

With acetic acid; at 80 ℃; for 4h;

DOI:10.1021/jo9808573

Reference yield:

ethyl 2,3,4-tri-O-benzyl-1,6-dialdo-1-thio-α-D-manno-pyranoside → (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-L-glycero-β-D-manno-heptopyranose (215381-20-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 59 percent / Mg, HgBr₂ / tetrahydrofuran / 20 - 24 °C

2: 83 percent / pyridine / 1.5 h / Ambient temperature

3: 85 percent / NIS, TfOH / CH₂Cl₂; diethyl ether / 0.42 h

4: H₂ / Pd/C / aq. ethanol / 16 h / 6080 Torr

5: p-toluenesulfonic acid / dimethylformamide / 0.25 h / Ambient temperature; pH 2

6: 84 percent / sym-collidine / CH₂Cl₂; dimethylformamide / -78 °C

7: 77 percent / AgOTf / CH₂Cl₂; toluene / 0.5 h / 0 °C

8: 85 percent / aq. HOAc / 4 h / 80 °C

With pyridine; 2,4,6-trimethyl-pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; hydrogen; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; magnesium; acetic acid; mercury dibromide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo9808573

Reference yield:

1,6-anhydro-2,3,4,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose (215381-41-2) → (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-L-glycero-β-D-manno-heptopyranose (215381-20-7)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Pd/C / aq. ethanol / 16 h / 6080 Torr

2: p-toluenesulfonic acid / dimethylformamide / 0.25 h / Ambient temperature; pH 2

3: 84 percent / sym-collidine / CH₂Cl₂; dimethylformamide / -78 °C

4: 77 percent / AgOTf / CH₂Cl₂; toluene / 0.5 h / 0 °C

5: 85 percent / aq. HOAc / 4 h / 80 °C

With 2,4,6-trimethyl-pyridine; hydrogen; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo9808573

upstream raw materials:

(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-2,3-O-isopropylidene-L-glycero-β-D-manno-heptopyranose

7-O-acetyl-1,6-anhydro-L-glycero-β-D-manno-heptopyranose

1,6-anhydro-2,3,4-tri-O-benzyl-7,8-dideoxy-β-D-manno-oct-7-enopyranose

1,6-anhydro-2,3,4-tri-O-benzyl-L-glycero-β-D-manno-heptopyranose

Downstream raw materials:

(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-3-O-benzoyl-L-glycero-β-D-manno-heptopyranose

(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-2-O-benzyl-L-glycero-β-D-manno-heptopyranose