Benzyl 2-Acetamido-2-deoxy-4,6-O-isopropylidene-b-D-glucopyranoside

Base Information

• Chemical Name: Benzyl 2-Acetamido-2-deoxy-4,6-O-isopropylidene-b-D-glucopyranoside
• CAS No.: 50605-12-4
• Molecular Formula: C18H25NO6
• Molecular Weight: 351.4
• Hs Code.: 29389090
• Mol file: 50605-12-4.mol

Synonyms:N-[(6R,7S,8R,8aS)-6-Benzyloxy-8-hydroxy-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide;

Chemical Property of Benzyl 2-Acetamido-2-deoxy-4,6-O-isopropylidene-b-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 173.5-175.5 °C
• Refractive Index: 1.561
• Boiling Point: 567.57 °C at 760 mmHg
• Flash Point: 297.056 °C
• PSA: 86.25000
• Density: 1.259 g/cm³
• LogP: 1.33610
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: An intermediate in the synthesis of Lipid A, which is known to be responsible for most of the biological activities of the lipopolysaccharide of gram-negative bacteria

Technology Process of Benzyl 2-Acetamido-2-deoxy-4,6-O-isopropylidene-b-D-glucopyranoside

There total 7 articles about Benzyl 2-Acetamido-2-deoxy-4,6-O-isopropylidene-b-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: 68.0%

2,2-dimethoxy-propane (77-76-9) + benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside (3055-51-4,3554-93-6,10380-86-6,13343-62-9,13343-67-4,19374-70-0,33423-30-2,33501-36-9,41355-95-7,86834-14-2,111003-11-3,347411-88-5) → benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (50605-12-4)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; for 4h; Ambient temperature;

DOI:10.1016/S0008-6215(00)81873-X

Reference yield:

benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside (3055-51-4,3554-93-6,10380-86-6,13343-62-9,13343-67-4,19374-70-0,33423-30-2,33501-36-9,41355-95-7,86834-14-2,111003-11-3,347411-88-5) + 2,2-dimethoxy-propane (77-76-9) → N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide (66026-10-6) + benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (50605-12-4)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; for 6h;

DOI:10.1021/jo9621534

Reference yield:

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3) → benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (50605-12-4)

Guidance literature:

Multi-step reaction with 3 steps

1: iron(III) trifluoromethanesulfonate / dichloromethane / 24 h / 20 °C / Inert atmosphere

2: sodium methylate; methanol / 0.5 h / 20 °C / Inert atmosphere

3: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 1 h / 40 °C / 187.52 Torr / Inert atmosphere

With methanol; iron(III) trifluoromethanesulfonate; sodium methylate; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/c7ob01201b

upstream raw materials:

2,2-dimethoxy-propane

benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside

benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside

2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate

Downstream raw materials:

benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranoside

C₁₉H₂₉NO₁₀*ClH

benzyl O-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

Refernces

• 1、 Sutherlin, Daniel P.,Armstrong, Robert W.. "Synthesis of 12 Stereochemically and Structurally Diverse C-Trisaccharides". . p. 5267 - 5283. Retrieved 2007/10/03.
• 2、 Rana,Barlow,Matta. "The chemical synthesis of O-alpha-L-fucopyranosyl-(1 goes to 2)-O-beta-D-galactopyranosyl-(1 goes to 3)-O-[alpha-L-fucopyranosyl-(1 goes to 4)]-2-acetamido-2-deoxy-D-glucopyranose, the Lewis b blood-group antigenic determinant.". . p. 231 - 239. Retrieved 2007/10/02.