betulinic acid 3β-O-3'-O-allyl-4',6'-O-benzylidene-β-D-glucopyranoside

Base Information

• Chemical Name: betulinic acid 3β-O-3'-O-allyl-4',6'-O-benzylidene-β-D-glucopyranoside
• CAS No.: 1334393-34-8
• Molecular Formula: C₄₆H₆₆O₈
• Molecular Weight: 747.025

Synonyms:betulinic acid 3β-O-3'-O-allyl-4',6'-O-benzylidene-β-D-glucopyranoside

Chemical Property of betulinic acid 3β-O-3'-O-allyl-4',6'-O-benzylidene-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of betulinic acid 3β-O-3'-O-allyl-4',6'-O-benzylidene-β-D-glucopyranoside

There total 2 articles about betulinic acid 3β-O-3'-O-allyl-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: 86.0%

3β-O-3'-O-allyl-2'-O-benzoyl-4',6'-O-benzylidene-β-D-glucopyranoside (1334393-19-9) → betulinic acid 3β-O-3'-O-allyl-4',6'-O-benzylidene-β-D-glucopyranoside (1334393-34-8)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; methanol; at 40 ℃;

DOI:10.1021/ol202232v

Reference yield:

Betulinic acid (472-15-1) → betulinic acid 3β-O-3'-O-allyl-4',6'-O-benzylidene-β-D-glucopyranoside (1334393-34-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere

2.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve

2.2: 20 °C / Inert atmosphere

3.1: water; sodium hydroxide / tetrahydrofuran; methanol / 40 °C

With 1H-imidazole; dmap; water; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol202232v

Reference yield: 92.0%

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate (1221151-98-9) + betulinic acid 3β-O-3'-O-allyl-4',6'-O-benzylidene-β-D-glucopyranoside (1334393-34-8) → 28-O-2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosylbetulinate 3β-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-3'-O-allyl-4',6'-O-benzylidene-β-D-glucopyranoside (1334393-36-0)

Guidance literature:

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate; betulinic acid 3β-O-3'-O-allyl-4',6'-O-benzylidene-β-D-glucopyranoside; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol202232v

upstream raw materials:

3β-O-3'-O-allyl-2'-O-benzoyl-4',6'-O-benzylidene-β-D-glucopyranoside

Betulinic acid

Downstream raw materials:

28-O-2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosylbetulinate 3β-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-3'-O-allyl-4',6'-O-benzylidene-β-D-glucopyranoside

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