(3β,5β,14β,17β)-3-<(2,3,4,6-tetra-O-benzyl-β-L-glucopyranosyl)oxy>-14-hydroxycard-20(22)-enolide

Base Information

• Chemical Name: (3β,5β,14β,17β)-3-<(2,3,4,6-tetra-O-benzyl-β-L-glucopyranosyl)oxy>-14-hydroxycard-20(22)-enolide
• CAS No.: 104048-31-9
• Molecular Formula: C₅₇H₆₈O₉
• Molecular Weight: 897.162

Synonyms:(3β,5β,14β,17β)-3-<(2,3,4,6-tetra-O-benzyl-β-L-glucopyranosyl)oxy>-14-hydroxycard-20(22)-enolide

Chemical Property of (3β,5β,14β,17β)-3-<(2,3,4,6-tetra-O-benzyl-β-L-glucopyranosyl)oxy>-14-hydroxycard-20(22)-enolide

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Technology Process of (3β,5β,14β,17β)-3-<(2,3,4,6-tetra-O-benzyl-β-L-glucopyranosyl)oxy>-14-hydroxycard-20(22)-enolide

There total 4 articles about (3β,5β,14β,17β)-3-<(2,3,4,6-tetra-O-benzyl-β-L-glucopyranosyl)oxy>-14-hydroxycard-20(22)-enolide 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: 39.0%

2,3,4,6-tetra-O-benzyl-β-L-glucopyranosyl-1-O-diphenyl-ketene-p-tolylimidate (104048-34-2) + (+)-digitoxigenin (143-62-4) → (3β,5β,14β,17β)-3-<(2,3,4,6-tetra-O-bezyl-α-L-glucopyranosyl)oxy>-14-hydroxycard-20(22)-enolide (104048-32-0) + (3β,5β,14β,17β)-3-<(2,3,4,6-tetra-O-benzyl-β-L-glucopyranosyl)oxy>-14-hydroxycard-20(22)-enolide (104048-31-9)

Guidance literature:

With molecular sieve; zinc trifluoromethanesulfonate; In dichloromethane; for 15h; Ambient temperature;

DOI:10.1016/S0040-4020(01)91342-0

Reference yield: 20.0%

2,3,4,6-tetra-O-benzyl-β-L-glucopyranosyl-1-O-trichloroacetimidate (104048-33-1) + (+)-digitoxigenin (143-62-4) → (3β,5β,14β,17β)-3-<(2,3,4,6-tetra-O-bezyl-α-L-glucopyranosyl)oxy>-14-hydroxycard-20(22)-enolide (104048-32-0) + (3β,5β,14β,17β)-3-<(2,3,4,6-tetra-O-benzyl-β-L-glucopyranosyl)oxy>-14-hydroxycard-20(22)-enolide (104048-31-9)

Guidance literature:

With molecular sieve; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -10 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)91342-0

Reference yield: 19.26%

2,3,4,6-tetra-O-benzyl-α-L-glucopyranosyl-1-O-trichloroacetimidate (104048-30-8) + (+)-digitoxigenin (143-62-4) → (3β,5β,14β,17β)-3-<(2,3,4,6-tetra-O-bezyl-α-L-glucopyranosyl)oxy>-14-hydroxycard-20(22)-enolide (104048-32-0) + (3β,5β,14β,17β)-3-<(2,3,4,6-tetra-O-benzyl-β-L-glucopyranosyl)oxy>-14-hydroxycard-20(22)-enolide (104048-31-9)

Guidance literature:

With molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -30 ℃; for 3h;

DOI:10.1016/S0040-4020(01)91342-0

upstream raw materials:

2,3,4,6-tetra-O-benzyl-β-L-glucopyranosyl-1-O-diphenyl-ketene-p-tolylimidate

(+)-digitoxigenin

2,3,4,6-tetra-O-benzyl-α-L-glucopyranosyl-1-O-trichloroacetimidate

2,3,4,6-tetra-O-benzyl-β-L-glucopyranosyl-1-O-trichloroacetimidate

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