Einecs 254-989-0

Base Information

• Chemical Name: Einecs 254-989-0
• CAS No.: 40591-65-9
• Molecular Formula: C15H22 N2 O9 S . Br H
• Molecular Weight: 487.326
• NSC Number: 409734,129246
• DSSTox Substance ID: DTXSID00961001
• Mol file: 40591-65-9.mol

Synonyms:NSC 409734;EINECS 254-989-0;2,3,4,6-Tetra-O-acetyl-1-carbamimidoyl-1-thio-beta-D-glucopyranosemonohydrobromide;Diethyl4-methoxybenzalmalonate;DTXSID00961001;[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-carbamimidoylsulfanyloxan-2-yl]methyl acetate;hydrobromide;NSC129246;NSC409734;NSC-129246;NSC-409734;BS-25070;FT-0674894;FT-0674902;2,3,4,6-Tetra-O-acetyl-1-S-carbamimidoyl-1-thiohexopyranose--hydrogen bromide (1/1)

Chemical Property of Einecs 254-989-0

Chemical Property:

• Appearance/Colour: White Crystalline Solid
• Melting Point: 205-216°C
• Boiling Point: 490.9 °C at 760 mmHg
• Flash Point: 250.7 °C
• PSA: 189.60000
• Density: 1.49g/cm³
• LogP: 1.45430
• Solubility.: Chloroform, Dichloromethane, Ethanol, Methanol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 486.03076
• Heavy Atom Count: 28
• Complexity: 612

Purity/Quality:

99% ^*data from raw suppliers

2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)thiopseudoUreaHydrobromide ^*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)SC(=N)N)OC(=O)C)OC(=O)C)OC(=O)C.Br
• Uses: 2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)thiopseudo Urea Hydrobromide (cas# 40591-65-9) is a compound useful in organic synthesis.

Technology Process of Einecs 254-989-0

There total 18 articles about Einecs 254-989-0 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%

thiourea (17356-08-0) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide (40591-65-9)

Guidance literature:

In acetone; at 60 ℃; Inert atmosphere; Reflux;

DOI:10.3987/COM-20-S(K)73

Reference yield: 88.0%

thiourea (17356-08-0) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → 2,3,4,6-tetra-O-acetylgalactopyranosyl-1-β-pseudothiourea hydrobromide (40591-65-9,51224-13-6,51898-28-3,57030-42-9,106818-92-2)

Guidance literature:

In acetone; for 0.05h; microwave irradiation;

DOI:10.1080/07328300500282540

Reference yield: 76.0%

D-Galactose (10257-28-0) + acetic anhydride (108-24-7) + thiourea (17356-08-0) → 2,3,4,6-tetra-O-acetylgalactopyranosyl-1-β-pseudothiourea hydrobromide (40591-65-9,51224-13-6,51898-28-3,57030-42-9,106818-92-2)

Guidance literature:

D-Galactose; acetic anhydride; With perchloric acid; at 20 - 25 ℃; for 1.5h;

With hydrogen bromide; at 15 ℃; for 1h;

thiourea; In acetonitrile; at 60 - 70 ℃; for 0.5h;

upstream raw materials:

thiourea

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

α-D-glucopyranose peracetylate

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

Downstream raw materials:

methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

2-(trifluoroacetylamino)ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranose

phenyl 4-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-thioglucopyranoside

Refernces

• 1、 Erfurt, Karol,Hadasik, Agnieszka,Krawczyk, Monika,Pastuch-Gawo?ek, Gabriela. "8-Hydroxyquinoline glycoconjugates containing sulfur at the sugar anomeric position—synthesis and preliminary evaluation of their cytotoxicity". . . Retrieved 2020/09/18.
• 2、 Brink?, Anne,Risinger, Christian,Lambert, Annie,Blixt, Ola,Grandjean, Cyrille,Jensen, Henrik H.. "Combining Click Reactions for the One-Pot Synthesis of Modular Biomolecule Mimetics". supporting information. p. 7544 - 7548. Retrieved 2019/10/08.