diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-3)-4,6-O-benzylidene-β-D-glucopyranoside

Base Information

• Chemical Name: diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-3)-4,6-O-benzylidene-β-D-glucopyranoside
• CAS No.: 211797-95-4
• Molecular Formula: C₆₆H₉₀O₂₄
• Molecular Weight: 1267.43
• Mol file: 211797-95-4.mol

Synonyms:diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-3)-4,6-O-benzylidene-β-D-glucopyranoside

Chemical Property of diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-3)-4,6-O-benzylidene-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-3)-4,6-O-benzylidene-β-D-glucopyranoside

There total 9 articles about diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-3)-4,6-O-benzylidene-β-D-glucopyranoside 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: 84.0%

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate (74808-10-9) + diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-β-D-glucopyranoside (211797-94-3) → diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-3)-4,6-O-benzylidene-β-D-glucopyranoside (211797-95-4)

Guidance literature:

With diethyl ether; 4 A molecular sieve; boron trifluoride; In dichloromethane; for 7h; Ambient temperature;

DOI:10.1016/S0008-6215(97)10050-7

Reference yield:

2,3,4,6-tetra-O-benzoylglucosyl bromide (14218-11-2) → diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-3)-4,6-O-benzylidene-β-D-glucopyranoside (211797-95-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 73 percent / mol sieves 4A, AgOTf / CH₂Cl₂; toluene / 4 h / -20 °C

2: 86 percent / NaOMe / methanol; CH₂Cl₂ / 6 h / Heating

3: 89 percent / CSA / dimethylformamide / 3 h / 40 °C

4: imidazole / dimethylformamide / 3 h / 40 - 50 °C

5: 100 percent / mol. sieves 4A, BF₃*Et₂O / CH₂Cl₂ / 3 h / Ambient temperature

6: 84 percent / nBu₄NF / tetrahydrofuran / 5.5 h / Ambient temperature

7: 84 percent / mol. sieves 4A, BF₃/*Et₂O / CH₂Cl₂ / 7 h / Ambient temperature

With 1H-imidazole; diethyl ether; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; boron trifluoride; tetrabutyl ammonium fluoride; sodium methylate; silver trifluoromethanesulfonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0008-6215(97)10050-7

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-3)-4,6-O-benzylidene-β-D-glucopyranoside (211797-95-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / CSA / dimethylformamide / 3 h / 40 °C

2: imidazole / dimethylformamide / 3 h / 40 - 50 °C

3: 100 percent / mol. sieves 4A, BF₃*Et₂O / CH₂Cl₂ / 3 h / Ambient temperature

4: 84 percent / nBu₄NF / tetrahydrofuran / 5.5 h / Ambient temperature

5: 84 percent / mol. sieves 4A, BF₃/*Et₂O / CH₂Cl₂ / 7 h / Ambient temperature

With 1H-imidazole; diethyl ether; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; boron trifluoride; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(97)10050-7

upstream raw materials:

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate

diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-β-D-glucopyranoside

2,3,4,6-tetra-O-benzoylglucosyl bromide

benzaldehyde dimethyl acetal

Downstream raw materials:

diosgenyl α-L-rhamnopyranosyl-(1->2)-[β-D-glucopyranosyl-(1->3)]-β-D-glucopyranoside

Refernces