octyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-β-D-glcopyranoside

Base Information

Chemical Name:octyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-β-D-glcopyranoside
CAS No.:314038-31-8
Molecular Formula:C₅₁H₇₂O₂₅
Molecular Weight:1085.12
Hs Code.:

Synonyms:octyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-β-D-glcopyranoside

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Chemical Property of octyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-β-D-glcopyranoside

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Technology Process of octyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-β-D-glcopyranoside

There total 8 articles about octyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-β-D-glcopyranoside 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: 79.0%

: 314038-30-7
Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

: 314038-29-4
octyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)-2,4-di-O-acetyl-β-D-glucopyranoside

: 314038-31-8
octyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-β-D-glcopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/ol000243w

Reference yield:

: 29836-26-8
n-octyl β-D-glucopyranoside

: 314038-31-8
octyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-β-D-glcopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 4-(dimethylamino)pyridine / pyridine / 16 h / 80 °C

2: imidazole / pyridine; dimethylformamide / 20 °C

3: pyridine / 50 °C

4: 90 percent / FeCl₃*6H₂O / CH₂Cl₂ / 3 h / 20 °C

5: TMSOTf / CH₂Cl₂ / 1 h / 0 °C

6: 1.52 g / TFA / CH₂Cl₂; H₂O / 4 h / 20 °C

7: 79 percent / TMSOTf / CH₂Cl₂ / 1 h / 0 °C

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; iron(III) chloride; trifluoroacetic acid; dmap; In pyridine; dichloromethane; water; N,N-dimethyl-formamide; 1: Condensation / 2: Silylation / 3: Acetylation / 4: Detritylation / 5: Glycosylation / 6: Hydrolysis / 7: Glycosylation;
DOI:10.1021/ol000243w

Reference yield:

: 92052-29-4
2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate

: 314038-31-8
octyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-β-D-glcopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: TMSOTf / CH₂Cl₂ / 1 h / 0 °C

2: 1.52 g / TFA / CH₂Cl₂; H₂O / 4 h / 20 °C

3: 79 percent / TMSOTf / CH₂Cl₂ / 1 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid; In dichloromethane; water; 1: Glycosylation / 2: Hydrolysis / 3: Glycosylation;
DOI:10.1021/ol000243w