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

Base Information

• Chemical Name: diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside
• CAS No.: 211797-93-2
• Molecular Formula: C₅₈H₈₆O₁₅Si
• Molecular Weight: 1051.4
• Mol file: 211797-93-2.mol

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

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

There total 7 articles about diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-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: 100.0%

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate (113893-72-4) + diosgenyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-β-D-glucopyranside → diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside (211797-93-2)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; for 3h; 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)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside (211797-93-2)

Guidance literature:

Multi-step reaction with 5 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

With 1H-imidazole; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; silver trifluoromethanesulfonate; In 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)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside (211797-93-2)

Guidance literature:

Multi-step reaction with 3 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

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

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

upstream raw materials:

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

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

benzaldehyde dimethyl acetal

diosgenin

Downstream raw materials:

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

ophiopogonin C

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

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

Refernces