2-(3-Methyl-3-nitrosoureido)-2-deoxy-D-mannopyranose 1,3,4,6-tetraacetate

Base Information

• Chemical Name: 2-(3-Methyl-3-nitrosoureido)-2-deoxy-D-mannopyranose 1,3,4,6-tetraacetate
• CAS No.: 136598-81-7
• Molecular Formula: C₁₆H₂₃N₃O₁₁
• Molecular Weight: 433.372
• Mol file: 136598-81-7.mol

Synonyms:1-Methyl-1-nitroso-3-(2-deoxy-1-O,3-O,4-O,6-O-tetraacetyl-D-mannopyranos-2-yl)urea;2-(3-Methyl-3-nitrosoureido)-2-deoxy-D-mannopyranose 1,3,4,6-tetraacetate

Chemical Property of 2-(3-Methyl-3-nitrosoureido)-2-deoxy-D-mannopyranose 1,3,4,6-tetraacetate

Chemical Property:

• Melting Point: 105 - 110 °C
• PSA: 176.20000
• LogP: -0.21680

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(3-Methyl-3-nitrosoureido)-2-deoxy-D-mannopyranose 1,3,4,6-tetraacetate

There total 3 articles about 2-(3-Methyl-3-nitrosoureido)-2-deoxy-D-mannopyranose 1,3,4,6-tetraacetate 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: 26.0%

1-methyl-1-nitroso-3-(2-deoxy-D-mannos-2-yl)urea (66395-17-3,66395-18-4,72521-89-2) + acetic anhydride (108-24-7) → 1-methyl-1-nitroso-3-(1,3,4,6-tetra-O-acetyl-2-deoxy-D-mannos-2-yl)urea (136598-81-7)

Guidance literature:

With pyridine; at 0 ℃; for 2h;

DOI:10.1002/jps.2600800717

Reference yield:

D-mannosamine (90-76-6,90-77-7,530-23-4,579-32-8,579-33-9,643-68-5,2596-19-2,6490-68-2,6490-70-6,6490-72-8,6490-73-9,6490-74-0,14196-84-0,14196-86-2,14257-69-3,58381-21-8) → 1-methyl-1-nitroso-3-(1,3,4,6-tetra-O-acetyl-2-deoxy-D-mannos-2-yl)urea (136598-81-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / 1M NaOH / diethyl ether; CHCl₃ / 1.) 0 deg C, 3 h, 2.) 25 deg C, 3 h

2: 27 percent / NaNO₂, HCl / ethanol; H₂O / 1.) 0 deg C, 30 min, 2.) 25 deg C, 1 h

3: 26 percent / pyridine / 2 h / 0 °C

With pyridine; hydrogenchloride; sodium hydroxide; sodium nitrite; In diethyl ether; ethanol; chloroform; water;

DOI:10.1002/jps.2600800717

Reference yield:

1-methyl-3-(2-deoxy-D-mannos-2-yl)urea (26922-56-5,72521-86-9) → 1-methyl-1-nitroso-3-(1,3,4,6-tetra-O-acetyl-2-deoxy-D-mannos-2-yl)urea (136598-81-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 27 percent / NaNO₂, HCl / ethanol; H₂O / 1.) 0 deg C, 30 min, 2.) 25 deg C, 1 h

2: 26 percent / pyridine / 2 h / 0 °C

With pyridine; hydrogenchloride; sodium nitrite; In ethanol; water;

DOI:10.1002/jps.2600800717

upstream raw materials:

1-methyl-1-nitroso-3-(2-deoxy-D-mannos-2-yl)urea

acetic anhydride

D-mannosamine

1-methyl-3-(2-deoxy-D-mannos-2-yl)urea

Refernces