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

Base Information

• Chemical Name: (3β,5β,14β,17β)-3β-<(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)oxy>-14-hydroxycard-20(22)-enolide
• CAS No.: 103383-07-9
• Molecular Formula: C₅₇H₆₈O₉
• Molecular Weight: 897.162
• Mol file: 103383-07-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (3β,5β,14β,17β)-3β-<(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)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: 62.0%

2,3,4,6-tetra-O-benzyl-β-D-mannopyranose 1-O-trichloroacetimidate (103368-06-5) + (+)-digitoxigenin (143-62-4) → (3β,5β,14β,17β)-3β-<(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)oxy>-14-hydroxycard-20(22)-enolide (103383-07-9) + (3β,5β,14β,17β)-3β-<(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)oxy>-14-hydroxycard-20(22)-enolide (103368-05-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; 1.) -10 deg C, 10 min, 2.) a.) -10 deg C, 15 min, b.) ) deg C, 10 min;

DOI:10.1021/jm00160a025

Reference yield: 18.0%

2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate (74808-09-6,90357-89-4,90358-01-3,103368-01-0,103368-04-3,103368-06-5,104048-30-8,104048-33-1,114743-70-3,132201-75-3,132748-02-8,83441-60-5) + (+)-digitoxigenin (143-62-4) → (3β,5β,14β,17β)-3β-<(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)oxy>-14-hydroxycard-20(22)-enolide (103383-07-9) + (3β,5β,14β,17β)-3β-<(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)oxy>-14-hydroxycard-20(22)-enolide (103368-05-4)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; 1.) RT, 10 min, 2.) -20 deg C, 2 h;

DOI:10.1021/jm00160a025

Reference yield:

methyl-α,β-D-mannopyranoside (51023-63-3) → (3β,5β,14β,17β)-3β-<(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)oxy>-14-hydroxycard-20(22)-enolide (103383-07-9)

Guidance literature:

Multi-step reaction with 4 steps

1: NaH / dimethylsulfoxide / 10 h / Ambient temperature

2: 80percent AcOH, 2 N H₂SO₄ / H₂O / 8 h / 90 °C

3: 1.) NaH / 1.) CH₂Cl₂, RT, 10 min, 2.) CH₂Cl₂, RT, 1 h

4: 61 percent / 1.) mol. sieves 4 Angstroem, 2.) BF₃*Et₂O / CH₂Cl₂ / 1.) RT, 10 min, 2.) -20 deg C, 2 h

With 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; sodium hydride; acetic acid; In dichloromethane; water; dimethyl sulfoxide;

DOI:10.1021/jm00160a025

upstream raw materials:

2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate

(+)-digitoxigenin

2,3,4,6-tetra-O-benzyl-β-D-mannopyranose 1-O-trichloroacetimidate

methyl-α,β-D-mannopyranoside