Acetagastrodine

Base Information

• Chemical Name: Acetagastrodine
• CAS No.: 64291-41-4
• Deprecated CAS: 105054-56-6
• Molecular Formula: C21H26O11
• Molecular Weight: 454.431
• UNII: B8N8L7P6PQ
• DSSTox Substance ID: DTXSID00214509
• Nikkaji Number: J81.913A
• Wikidata: Q72433963
• Mol file: 64291-41-4.mol

Synonyms:acetagastrodine

Chemical Property of Acetagastrodine

Chemical Property:

• Melting Point: 170-171 °C(Solv: ethanol (64-17-5))
• Boiling Point: 551.4 °C at 760 mmHg
• PKA: 14.42±0.10(Predicted)
• Flash Point: 184 °C
• PSA: 143.89000
• Density: 1.33 g/cm³
• LogP: 0.64080
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 12
• Exact Mass: 454.14751164
• Heavy Atom Count: 32
• Complexity: 671

Purity/Quality:

95-99% ^*data from raw suppliers

Acegastrodine >98%,StandardReferencesGrade ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC2=CC=C(C=C2)CO)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=CC=C(C=C2)CO)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of Acetagastrodine

There total 15 articles about Acetagastrodine 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%

4-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (2887-07-2,31873-42-4,148579-45-7) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(hydroxymethyl)phenoxy)-tetrahydro-2H-pyran-3,4,5-triyl triacetate (64291-41-4,105054-56-6)

Guidance literature:

With hydrogen; In methanol; at 20 ℃; for 2h; Reagent/catalyst; chemoselective reaction;

DOI:10.1016/j.tetlet.2015.09.154

Reference yield: 93.0%

4-(bromomethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (78617-45-5,148579-44-6) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(hydroxymethyl)phenoxy)-tetrahydro-2H-pyran-3,4,5-triyl triacetate (64291-41-4,105054-56-6)

Guidance literature:

With sodium hydrogencarbonate; In [⁽²⁾H₆]acetone; water; at 50 ℃; for 10h;

DOI:10.2298/JSC131011026L

Reference yield: 86.0%

gastrodin (62499-27-8,106982-96-1) + acetic acid (64-19-7,77671-22-8) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(hydroxymethyl)phenoxy)-tetrahydro-2H-pyran-3,4,5-triyl triacetate (64291-41-4,105054-56-6)

Guidance literature:

gastrodin; With potassium borohydride; In methanol; at 5 - 8 ℃; for 45h;

acetic acid; In methanol; for 0.0833333h; pH=5 - 6; Solvent; Temperature;

upstream raw materials:

4-(bromomethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

4-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

(4-hydroxyphenyl)methanol

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

Downstream raw materials:

4-(tetra-O-acetyl-β-D-glucopyranosyloxy)benzyl acetate

4-(bromomethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Refernces

• 1、 -. "DUAL PROTECTED PRO-COELENTERAZINE SUBSTRATES". Paragraph 0115; 0118-0119. . Retrieved 2018/03/30.
• 2、 -. "Synthesis method of gastrodin". Paragraph 0031; 0032; 0033; 0034. . Retrieved 2017/07/19.