2-Deoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose

Base Information

• Chemical Name: 2-Deoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose
• CAS No.: 66395-17-3
• Molecular Formula: C₈H₁₅N₃O₇
• Molecular Weight: 265.223
• European Community (EC) Number: 242-646-8
• UN Number: 3077
• UNII: 0G5XQ5N8KS
• Nikkaji Number: J1.586.028F
• Wikipedia: Streptozotocin
• Wikidata: Q27236748
• NCI Thesaurus Code: C845
• RXCUI: 10114
• Mol file: 66395-17-3.mol

Synonyms:2-Deoxy-2-((methylnitrosoamino)carbonyl)amino-D-glucose;Streptozocin;Streptozotocin;Streptozotocine;Zanosar

Chemical Property of 2-Deoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose

Chemical Property:

• XLogP3: -1.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 265.09099983
• Heavy Atom Count: 18
• Complexity: 315
• Transport DOT Label: Class 9

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Chemical Classes: Biological Agents -> Bacterial Toxins
• Drug Classes: Antineoplastic Agents
• Canonical SMILES: CN(C(=O)NC1C(C(C(OC1O)CO)O)O)N=O
• Isomeric SMILES: CN(C(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O)CO)O)O)N=O
• Recent ClinicalTrials: Two Chemotherapy Regimens Plus or Minus Bevacizumab
• Recent EU Clinical Trials: Randomized open label study to compare the efficacy and safety of everolimus followed by chemotherapy with STZ-5FU upon progression or the reverse sequence, chemotherapy with STZ-5FU followed by everolimus upon progression, in advanced progressive pNETs (SEQTOR study)

Technology Process of 2-Deoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose

There total 9 articles about 2-Deoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose 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: 28.0%

1-methyl-3-(2-deoxy-D-galactos-2-yl)urea (26922-56-5,72521-86-9) → 1-methyl-1-nitroso-3-(2-deoxy-D-galactos-2-yl)urea (66395-17-3,66395-18-4,72521-89-2)

Guidance literature:

With hydrogenchloride; sodium nitrite; In ethanol; water; 1.) 0 deg C, 30 min, 2.) 25 deg C, 1 h;

DOI:10.1002/jps.2600800717

Reference yield: 27.0%

1-methyl-3-(2-deoxy-D-mannos-2-yl)urea (26922-56-5,72521-86-9) → 1-methyl-1-nitroso-3-(2-deoxy-D-mannos-2-yl)urea (66395-17-3,66395-18-4,72521-89-2)

Guidance literature:

With hydrogenchloride; sodium nitrite; In ethanol; water; 1.) 0 deg C, 30 min, 2.) 25 deg C, 1 h;

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-(2-deoxy-D-mannos-2-yl)urea (66395-17-3,66395-18-4,72521-89-2)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1002/jps.2600800717

upstream raw materials:

N-Methyl-N'-(β-D-mannopyranosyl)-harnstoff

β-mannosamine

D-mannosamine hydrochloride

methyl isocyanate

Downstream raw materials:

1-methyl-1-nitroso-3-(1,3,4,6-tetra-O-acetyl-2-deoxy-D-mannos-2-yl)urea

1-methyl-1-nitroso-3-(1,3,4,6-tetra-O-acetyl-2-deoxy-D-galactos-2-yl)urea