3-O-[2-Acetamido-2-deoxy-beta-D-glucopyranosyl]-D-mannopyranose

Base Information

• Chemical Name: 3-O-[2-Acetamido-2-deoxy-beta-D-glucopyranosyl]-D-mannopyranose
• CAS No.: 210036-24-1
• Molecular Formula: C14H25NO11
• Molecular Weight: 383.35
• Hs Code.: 2932990090
• Mol file: 210036-24-1.mol

Synonyms:N-[(2S,3S,4R,5S)-4,5-Dihydroxy-6-(hydroxymethyl)-2-[(2R,3R,4S,5R)-2,3,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-4-yl]oxy-tetrahydropyran-3-yl]acetamide;

Chemical Property of 3-O-[2-Acetamido-2-deoxy-beta-D-glucopyranosyl]-D-mannopyranose

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 178-181°C
• Refractive Index: 1.624
• Boiling Point: 795.471 °C at 760 mmHg
• Flash Point: 434.886 °C
• PSA: 198.40000
• Density: 1.645 g/cm³
• LogP: -4.86250
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)

Purity/Quality:

98%Min ^*data from raw suppliers

3-O-[2-Acetamido-2-deoxy-β-D-glucopyranosyl]-D-mannopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-O-[2-Acetamido-2-deoxy-beta-D-glucopyranosyl]-D-mannopyranose

There total 38 articles about 3-O-[2-Acetamido-2-deoxy-beta-D-glucopyranosyl]-D-mannopyranose 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:

C21H31NO11 (1225015-63-3) → GalNac β1-3 Glc (491-85-0,22176-27-8,30688-41-6,38711-46-5,51921-39-2,62137-98-8,63121-25-5,79733-84-9,79733-85-0,97101-33-2,130794-38-6,130794-39-7,147127-57-9,210036-24-1)

Guidance literature:

With hydrogen; 1% Pd/C;

Reference yield:

benzyl 3-O-(2-acetamido-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2,4,6-tri-O-benzyl-D-galactopyranose → O-(2-acetamido-2-deoxy-β-D-glucopycanosyl)-<1,3>-D-galactose (491-85-0,210036-24-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; under 760 Torr; Yield given;

DOI:10.1016/S0008-6215(00)85613-X

Reference yield:

D-Glucose (2280-44-6) → O-(2-acetamio-2-deoxy-β-D-glucopyranosyl)-(1->3)-α-D-glucopyranose (62137-98-8,210036-24-1)

Guidance literature:

Multi-step reaction with 7 steps

2: 84 percent / KOH / 2 h / 110 °C

3: (NH₄)2Ce(NO₃)6, NaN₃ / acetonitrile / 1 h / -20 °C

4: 1.21 g / SiO₂ / toluene; butan-2-one / Ambient temperature

5: p-NO₂C₆H₄SO₂Cl, AgOTf, Et₃N / CH₂Cl₂ / 1) -60 deg C to 0 deg C, 2) overnight

6: 1) LiAlH₄ / 1) Et₂O, reflux

7: H₂, H₂O / Pd/C / acetic acid

With potassium hydroxide; lithium aluminium tetrahydride; sodium azide; ammonium cerium(IV) nitrate; water; hydrogen; silver trifluoromethanesulfonate; silica gel; triethylamine; 4-Nitrobenzenesulfonyl chloride; palladium on activated charcoal; In dichloromethane; acetic acid; toluene; acetonitrile; butanone;

DOI:10.1246/bcsj.72.765

upstream raw materials:

C₂₁H₃₁NO₁₁

benzyl O-(2-acetamio-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-glucopyranoside

D-Glucose

3,4,6-tri-O-benzyl-D-glucal

Downstream raw materials:

N-{(2S,3R,4R,5S,6R)-2-[(1R,2S)-1-(1,2-Dihydroxy-ethyl)-2,3,4-trihydroxy-butoxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide