Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside

Base Information

• Chemical Name: Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside
• CAS No.: 130539-43-4
• Molecular Formula: C16H19NO6S
• Molecular Weight: 353.396
• Mol file: 130539-43-4.mol

Synonyms:Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside

Chemical Property of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside

Chemical Property:

• Boiling Point: 594.3±50.0 °C(Predicted)
• PKA: 13.00±0.70(Predicted)
• PSA: 132.60000
• Density: 1.52±0.1 g/cm3(Predicted)
• LogP: -0.21880

Purity/Quality:

98% ^*data from raw suppliers

Ethyl2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside

There total 12 articles about Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-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: 100.0%

ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (99409-32-2) → ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (130539-43-4)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2h; Inert atmosphere;

Reference yield:

phthalic anhydride (85-44-9) → ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (130539-43-4)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydroxide / water / 24 h / 20 °C

2: pyridine

3: boron trifluoride diethyl etherate / chloroform / Reflux

4: methanol; sodium methylate

With pyridine; methanol; boron trifluoride diethyl etherate; sodium methylate; sodium hydroxide; In chloroform; water;

DOI:10.1016/j.carres.2011.05.024

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (130539-43-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 62.5 percent / BF₃*Et₂O / CH₂Cl₂ / 22 h

2: 69.5 percent / sodium methoxide / methanol / 3 h

With boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane;

DOI:10.1081/CAR-120020480

upstream raw materials:

ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

tetra-O-acetyl-2-(2-carboxy-benzoylamino)-2-deoxy-β-D-glucopyranose

Downstream raw materials:

ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-trifluoromethanesulfonyl-1-thio-β-D-glucopyranoside

ethyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-allopyranoside

ethyl 2-azido-4,6-O-benzylidene-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside

ethyl 2-azido-4,6-di-O-benzyl-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside

Refernces

• 1、 -. "LOW CONTAMINANT ANTIMICROBIAL VACCINES". Paragraph 0081; 0085. . Retrieved 2021/05/21.
• 2、 -. "Methods for inhibiting biofilm formation". Page/Page column 16; 18. . Retrieved 2020/11/23.