2-Propenyl 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)--D-glucopyranoside

Base Information

• Chemical Name: 2-Propenyl 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)--D-glucopyranoside
• CAS No.: 114853-29-1
• Molecular Formula: C17H19 N O7
• Molecular Weight: 349.34
• Mol file: 114853-29-1.mol

Synonyms:b-D-Glucopyranoside, 2-propenyl2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)- (9CI)

Chemical Property of 2-Propenyl 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)--D-glucopyranoside

Chemical Property:

• Refractive Index: 1.646
• PSA: 116.53000
• LogP: -0.76930
• Solubility.: Methanol

Purity/Quality:

99% ^*data from raw suppliers

Allyl 2-deoxy-2-phthalimido-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Propenyl 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)--D-glucopyranoside

There total 7 articles about 2-Propenyl 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)--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: 90.0%

allyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside (72333-26-7) → allyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (114853-29-1)

Guidance literature:

With hydrogenchloride; In acetone; at 70 ℃;

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-α-D-glucopyranosyl 2,2,2-trichloroacetimidate → allyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (114853-29-1)

Guidance literature:

Multi-step reaction with 2 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -20 °C / Molecular sieve; Inert atmosphere

2: sodium hydroxide; methanol / dichloromethane / 2 h / pH < 10

With methanol; trimethylsilyl trifluoromethanesulfonate; sodium hydroxide; In dichloromethane;

DOI:10.1002/asia.201801486

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → allyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (114853-29-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / HBr / acetic acid

2: 74 percent / Hg(CN)2

3: 53 percent / aq. HCl / acetone

With hydrogenchloride; hydrogen bromide; mercury(II) cyanide; In acetic acid; acetone;

upstream raw materials:

allyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

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

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide

phthalic anhydride

Downstream raw materials:

allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

allyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

allyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Refernces

• 1、 -. "SYNTHETIC OLIGOSACCHARIDES FOR STAPHYLOCOCCUS VACCINE". Page/Page column 40-41. . Retrieved 2012/11/07.
• 2、 Achkar, Jihane,Sanchez-Larraza, Isabel,Johnson, Carol A.,Wei, Alexander. "Synthesis and conformational analysis of 6-C-methyl-substituted 2-acetamido-2-deoxy-β-D-glucopyranosyl mono- and disaccharides". . p. 214 - 226. Retrieved 2007/10/03.