(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

Base Information

Chemical Name:(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
CAS No.:215381-22-9
Molecular Formula:C₅₀H₄₆O₁₆
Molecular Weight:902.906
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 16 articles about (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 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: 80.0%

: 100-39-0
benzyl bromide

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

: 215381-22-9
(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

Guidance literature:: (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-L-glycero-β-D-manno-heptopyranose; With di(n-butyl)tin oxide; In benzene; Heating;

benzyl bromide; With tetrabutylammomium bromide; In benzene; Heating;
DOI:10.1081/CAR-200044580

Reference yield:

: ethyl 2,3,4-tri-O-benzyl-1,6-dialdo-1-thio-α-D-manno-pyranoside

: 215381-22-9
(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

Guidance literature:: Multi-step reaction with 9 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

9: 1.) Bu₂SnO, 2.) Bu₄NI / 1.) benzene, 1 h, reflux, 2.) benzene, 12 h, reflux

With pyridine; 2,4,6-trimethyl-pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; hydrogen; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; 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:

: 215381-41-2
1,6-anhydro-2,3,4,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose

: 215381-22-9
(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

Guidance literature:: Multi-step reaction with 6 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

6: 1.) Bu₂SnO, 2.) Bu₄NI / 1.) benzene, 1 h, reflux, 2.) benzene, 12 h, reflux

With 2,4,6-trimethyl-pyridine; hydrogen; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo9808573