benzyl 3-O-(methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate))-18β-glycyrrhetinate

Base Information

• Chemical Name: benzyl 3-O-(methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate))-18β-glycyrrhetinate
• CAS No.: 127290-97-5
• Molecular Formula: C₅₀H₆₈O₁₃
• Molecular Weight: 877.082
• Mol file: 127290-97-5.mol

Synonyms:benzyl 3-O-(methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate))-18β-glycyrrhetinate

Chemical Property of benzyl 3-O-(methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate))-18β-glycyrrhetinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 3-O-(methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate))-18β-glycyrrhetinate

There total 4 articles about benzyl 3-O-(methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate))-18β-glycyrrhetinate 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: 54.0%

benzyl (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate (51984-75-9) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → benzyl 3-O-(methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate))-18β-glycyrrhetinate (127290-97-5)

Guidance literature:

With silver zeolite; In dichloromethane; at 20 ℃; for 96h; Darkness;

DOI:10.1016/j.carres.2009.04.015

Reference yield: 25.4%

benzyl (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate (51984-75-9) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → benzyl 11-oxo-A-neooleana-3(5),12-dien-30-oate + benzyl 3β-acetyloxy-11-oxo-olean-12-en-30-oate (127290-98-6) + benzyl 3-O-(methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate))-18β-glycyrrhetinate (127290-97-5)

Guidance literature:

With calcium sulfate; mercury(II) cyanide; In nitromethane; benzene; Heating;

DOI:10.1248/cpb.38.221

Reference yield:

enoxolone (471-53-4) → benzyl 3-O-(methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate))-18β-glycyrrhetinate (127290-97-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / CHCl₃ / 5 h / Heating

2: 46.4 percent / Ag₂CO₃, CaSO₄ / 1,2-dichloro-ethane

With calcium sulfate; silver carbonate; In chloroform; 1,2-dichloro-ethane;

DOI:10.1248/cpb.38.221

upstream raw materials:

benzyl (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

enoxolone

O-benzyl-N,N'-dicyclohexylisourea

Downstream raw materials:

benzyl 3β-(glucuron-1'β-yl)-glycyrrhetate

succinimidyl N-<3β-(tert-butylglucuron-1'β-yl)-glycyrrhetyl>-Amcha

benzyl N-<3β-(tert-butylglucuron-1'β-yl)-glycyrrhetyl>-Amcha

benzyl N-<3β-(tert-butylglucuron-1'β-yl)-glycyrrhetyl>-glycinate