(R,S)-4-Hydroxy Cyclophosphamide

Base Information

• Chemical Name: (R,S)-4-Hydroxy Cyclophosphamide
• CAS No.: 61903-30-8
• Molecular Formula: C₇H₁₅Cl₂N₂O₃P
• Molecular Weight: 277.087
• Mol file: 61903-30-8.mol

Synonyms:(2R,4S)-rel-2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorin-4-ol 2-Oxide;(R,S)-4-Hydroxy Cyclophosphamide;(R,S)-4-Hydroxy Cyclophosphamide Discontinued See: H926301;(R,S)-4-Hydroxy Cyclophosphamide Kit;(R,S)-4-Hydroxy Cyclophosphamide See: H926301;(R,S)-4-Hydroxy Cyclophosphamide, Preparation Kit

Chemical Property of (R,S)-4-Hydroxy Cyclophosphamide

Chemical Property:

• PSA: 71.61000
• LogP: 1.53120
• Storage Temp.: Hygroscopic, -86°C Freezer, Under Inert Atmosphere
• Solubility.: Water

Purity/Quality:

99% ^*data from raw suppliers

(R,S)-4-HydroxyCyclophosphamidePreparationKit ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A metabolite of Cyclophosphamide. This Kit consists of a vial of the precursor, 4-hydroperoxycyclophosphamide (H714675), and a vial of a reducing agent. Simply add water to the reducing agent until it is completely dissolved and add this solution to the precursor. This solution has a half-life of approximately 200 minutes at room temperature. Detailed instructions are enclosed.

Technology Process of (R,S)-4-Hydroxy Cyclophosphamide

There total 18 articles about (R,S)-4-Hydroxy Cyclophosphamide 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:

cis-4-Hydroperoxycyclophosphamide (56922-83-9) → cis-4-hydroxycyclophosphamide (61903-29-5,88852-77-1,40277-05-2,61903-30-8,88852-78-2)

Guidance literature:

With dimethylsulfide; In methanol; for 0.0833333h;

DOI:10.1021/jm00127a016

Reference yield:

O-3-buten-1-yl N,N-bis(2-chloroethyl)phosphorodiamidate (39800-29-8) → cis-4-hydroxycyclophosphamide (61903-29-5,88852-77-1,40277-05-2,61903-30-8,88852-78-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 27 percent / ozone, 30percent aq. H₂O₂ / acetone; H₂O / Ambient temperature

2: Ph₃P / CH₂Cl₂ / 0.25 h / Ambient temperature

With dihydrogen peroxide; ozone; triphenylphosphine; In dichloromethane; water; acetone;

DOI:10.1021/jm00370a008

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

upstream raw materials:

aldophosphamide

trans-4-hydroperoxycyclophosphamide

aldophosphamide hydrate

trans-4-hydroxycyclophosphamide

Downstream raw materials:

aldophosphamide

aldophosphamide hydrate

trans-4-hydroxycyclophosphamide

trans-4-hydroxycyclophosphamide

Refernces

• 1、 Borch, Richard F.,Millard, Jo Ann. "The Mechanism of Activation of 4-Hydroxycyclophosphamide". . p. 427 - 431. 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.