(3beta,5beta,8xi,9xi,12beta)-3-(beta-D-glycero-hexopyranosyloxy)-12,14-dihydroxycard-20(22)-enolide

Base Information

• Chemical Name: (3beta,5beta,8xi,9xi,12beta)-3-(beta-D-glycero-hexopyranosyloxy)-12,14-dihydroxycard-20(22)-enolide
• CAS No.: 25817-75-8
• Molecular Formula: C₂₉H₄₄O₁₀
• Molecular Weight: 552.662
• Mol file: 25817-75-8.mol

Synonyms:5b-Card-20(22)-enolide, 3b-(b-D-glucopyranosyloxy)-12b,14-dihydroxy- (8CI); Glucopyranoside, 3b,12b,14-trihydroxy-5b-card-20(22)-enolide-3, b-D- (8CI); Glucopyranoside, digoxigenin-3, b-D- (8CI)

Chemical Property of (3beta,5beta,8xi,9xi,12beta)-3-(beta-D-glycero-hexopyranosyloxy)-12,14-dihydroxycard-20(22)-enolide

Chemical Property:

• Vapor Pressure: 1.88E-27mmHg at 25°C
• Boiling Point: 771.1°Cat760mmHg
• Flash Point: 251.3°C
• Density: 1.41g/cm³

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3beta,5beta,8xi,9xi,12beta)-3-(beta-D-glycero-hexopyranosyloxy)-12,14-dihydroxycard-20(22)-enolide

There total 11 articles about (3beta,5beta,8xi,9xi,12beta)-3-(beta-D-glycero-hexopyranosyloxy)-12,14-dihydroxycard-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: 61.0%

3β-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-12-O-acetyldigoxigenin → digoxigenin 3β-β-D-glucoside (25817-75-8)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 5h; pH=9;

DOI:10.1016/j.ejmech.2017.12.086

Reference yield: 14.0%

digoxigenin 3β-β-D-glucoside tetraacetate (79317-29-6) → digoxigenin 3β-β-D-glucoside (25817-75-8)

Guidance literature:

With water; triethylamine; In methanol; for 72h; Ambient temperature;

Reference yield:

UDP-glucose (133-89-1) + digoxigenin (1672-46-4) → digoxigenin 3β-β-D-glucoside (25817-75-8)

Guidance literature:

With UGT₇₄AN₁; magnesium chloride; In aq. buffer; at 37 ℃; for 12h; pH=8; Enzymatic reaction;

DOI:10.1021/acs.orglett.7b03619

upstream raw materials:

digoxigenin 3β-β-D-glucoside tetraacetate

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

digoxigenin

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Refernces

• 1、 Makarevich. "". . . Retrieved 1969.
• 2、 Wen, Chao,Huang, Wei,Zhu, Xue-Lin,Li, Xiao-San,Zhang, Fan,Jiang, Ren-Wang. "UGT74AN1, a Permissive Glycosyltransferase from Asclepias curassavica for the Regiospecific Steroid 3-O-Glycosylation". supporting information. p. 534 - 537. Retrieved 2018/02/10.