Aldophosphamide

Base Information

• Chemical Name: Aldophosphamide
• CAS No.: 35144-64-0
• Molecular Formula: C7H15Cl2N2O3P
• Molecular Weight: 277.087
• UNII: 7AM2ILM9FI
• DSSTox Substance ID: DTXSID60956594
• Nikkaji Number: J415.698F
• Wikipedia: Aldophosphamide
• Wikidata: Q15711205
• Metabolomics Workbench ID: 68083
• ChEMBL ID: CHEMBL1593
• Mol file: 35144-64-0.mol

Synonyms:aldophosphamide;cyclophosphamide-mustard;Cyp-mustard

Chemical Property of Aldophosphamide

Chemical Property:

• Vapor Pressure: 2.95E-06mmHg at 25°C
• Boiling Point: 388.9°C at 760 mmHg
• Flash Point: 189°C
• PSA: 82.44000
• Density: 1.347g/cm³
• LogP: 2.13870
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 276.0197347
• Heavy Atom Count: 15
• Complexity: 224

Purity/Quality:

99% ^*data from raw suppliers

ALDOPHOSPHAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(COP(=O)(N)N(CCCl)CCCl)C=O

Technology Process of Aldophosphamide

There total 7 articles about Aldophosphamide 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:

trans-4-hydroperoxycyclophosphamide (39800-16-3,56922-83-9,61903-31-9,62435-42-1,146566-40-7) → aldophosphamide (35144-64-0) + cis-4-hydroxycyclophosphamide (61903-29-5,88852-77-1,40277-05-2,61903-30-8,88852-78-2)

Guidance literature:

With triphenylphosphine; In dichloromethane; for 0.25h; Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/jm00370a008

Reference yield:

cis-Mosfosfamide (84210-72-0,88859-04-5) → aldophosphamide (35144-64-0) + aldophosphamide hydrate (88685-78-3) + cis-4-hydroxycyclophosphamide (61903-29-5,88852-77-1,40277-05-2,61903-30-8,88852-78-2) + trans-4-hydroxycyclophosphamide (61903-30-8,88852-78-2,40277-05-2,61903-29-5,88852-77-1) + C9H21Cl2N2O6PS2 (105639-84-7) + 2-{(2S,4S)-2-[Bis-(2-chloro-ethyl)-amino]-2-oxo-2λ5-[1,3,2]oxazaphosphinan-4-ylsulfanyl}-ethanesulfonic acid (92745-18-1,88859-04-5)

Guidance literature:

With acetate bufer; In water; at 37 ℃; Rate constant; Mechanism; var. buffer conc., var. pH, var. ionic strength;

DOI:10.1021/jm00385a023

Reference yield:

trans-4-hydroperoxycyclophosphamide (39800-16-3,56922-83-9,61903-31-9,62435-42-1,146566-40-7) → phosphoramide mustard (10159-53-2) + aldophosphamide (35144-64-0) + C4H11N2O8PS4(2-)*2Na(1+) (88802-97-5) + aldophosphamide hydrate (88685-78-3) + cis-4-hydroxycyclophosphamide (61903-29-5,88852-77-1,40277-05-2,61903-30-8,88852-78-2) + trans-4-hydroxycyclophosphamide (61903-30-8,88852-78-2,40277-05-2,61903-29-5,88852-77-1)

Guidance literature:

With lutidine buffer; sodium thiosulfate; at 37 ℃; Product distribution;

DOI:10.1021/jm00370a008

upstream raw materials:

cyclophosphamide

mesna

cis-4-hydroxycyclophosphamide

trans-4-hydroperoxycyclophosphamide

Downstream raw materials:

C₈H₁₆Cl₂N₃O₃P

phosphoramide mustard

aldophosphamide hydrate

cis-4-hydroxycyclophosphamide

Refernces

• 1、 Kwon, Chul-Hoon,Borch, Richard F.,Engel, Jurgen,Niemeyer, Ulf. "Activation Mechanisms of Mafosfamide and the Role of Thiols in Cyclophosphamide Metabolism". . p. 395 - 399. Retrieved 2007/10/02.
• 2、 Borch,Hoye,Swanson. "In situ preparation and fate of cis-4-hydroxycyclophosphamide and aldophosphamide: 1H and 31P NMR evidence for equilibration of cis- and trans-4-hydroxycyclophosphamide with aldophosphamide and its hydrate in aqueous solution". . p. 490 - 494. Retrieved 2007/10/02.