Diallyl N,N-diisopropylphosphoramidite

Base Information

• Chemical Name: Diallyl N,N-diisopropylphosphoramidite
• CAS No.: 126429-21-8
• Molecular Formula: C12H24 N O2 P
• Molecular Weight: 245.302
• European Community (EC) Number: 625-730-2
• DSSTox Substance ID: DTXSID20405573
• Nikkaji Number: J1.108.929A
• Wikidata: Q82210190
• Mol file: 126429-21-8.mol

Synonyms:126429-21-8;Diallyl N,N-diisopropylphosphoramidite;diallyl diisopropylphosphoramidite;N-bis(prop-2-enoxy)phosphanyl-N-propan-2-ylpropan-2-amine;Phosphoramidous acid, N,N-bis(1-methylethyl)-, di-2-propen-1-yl ester;bis(allyloxy)(diisopropylamino)phosphine;Phosphoramidous acid, bis(1-methylethyl)-, di-2-propenyl ester;SCHEMBL386395;diallyldiisopropylphosphoramidite;DTXSID20405573;QBLCHHSGJTUNSJ-UHFFFAOYSA-N;MFCD00216647;AKOS015895011;di-allyl-N,N-diisopropylphosphoramidite;Diallyl N,N-di isopropyl phosphoramidite;SY121067;DIALLYLN,N-DIISOPROPYLPHOSPHORAMIDITE;FT-0756764;E80445;A929831;J-005381

Chemical Property of Diallyl N,N-diisopropylphosphoramidite

Chemical Property:

• Vapor Pressure: 0.111mmHg at 25°C
• Refractive Index: n20/D 1.456(lit.)
• Boiling Point: 220.8°Cat760mmHg
• PKA: 4.96±0.70(Predicted)
• Flash Point: 87.4°C
• PSA: 35.29000
• Density: g/cm³
• LogP: 3.73730
• Storage Temp.: 2-8°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 245.15446601
• Heavy Atom Count: 16
• Complexity: 187

Purity/Quality:

98%,99%, ^*data from raw suppliers

Diallyl N,N-diisopropylphosphoramidite ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)N(C(C)C)P(OCC=C)OCC=C
• Uses: Precursor involved in the synthesis of pharmacologically active molecules including:? ;Selective orally active S1P1 agonists1? ;Water-soluble prodrugs of triazole CS-758 with antifungal activity2? ;Fostriecin analogs as antitumor agents3Reactant involved in: ? ;Phosphitylation of alcohols4? ;Deallylation for the synthesis of nucleoside phosphoramidite5? ;Posphitylation and stereoselective Pudovik rearrangement6 Diallyl N,N-diisopropylphosphoramidite is a reagent used in the synthesis of Leustroducsin B that exhibits large variety of biological activities. It also acts as a reagent in the synthesis of water-soluble prodrugs of triazole CS-758 with antifungal activities. Precursor involved in the synthesis of pharmacologically active molecules including:Selective orally active S1P1 agonistsWater-soluble prodrugs of triazole CS-758 with antifungal activityFostriecin analogs as antitumor agentsReactant involved in: Phosphitylation of alcoholsDeallylation for the synthesis of nucleoside phosphoramiditePosphitylation and stereoselective Pudovik rearrangement

Technology Process of Diallyl N,N-diisopropylphosphoramidite

There total 2 articles about Diallyl N,N-diisopropylphosphoramidite 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: 84.0%

(allyloxy)bis(diisopropylamino)phosphine (108554-72-9) + allyl alcohol (107-18-6) → diallyl diisopropylphosphoramidite (126429-21-8)

Guidance literature:

With N,N-diisopropylamine tetrazolide; In dichloromethane; for 3h;

DOI:10.1016/S0040-4039(01)80694-8

Reference yield:

diisopropylamine (108-18-9) → diallyl diisopropylphosphoramidite (126429-21-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) pyridine, PCl₃ / 1.) one equivalent 2-propen-1-ol, -78 deg C, 90 min, diethyl ether 2.) -10 deg C, 60 min

2: 84 percent / diisopropylammonium tetrazolide / CH₂Cl₂ / 3 h

With pyridine; N,N-diisopropylamine tetrazolide; phosphorus trichloride; In dichloromethane;

DOI:10.1016/S0040-4039(01)80694-8

Reference yield: 99.0%

C39H53NO11 + diallyl diisopropylphosphoramidite (126429-21-8) → C45H62NO14P

Guidance literature:

C₃₉H₅₃NO₁₁; diallyl diisopropylphosphoramidite; With pyridinium trifluroacetate; In dichloromethane; at 20 - 25 ℃;

With dihydrogen peroxide; In dichloromethane; water; at 0 - 5 ℃; for 0.25h;

upstream raw materials:

(allyloxy)bis(diisopropylamino)phosphine

allyl alcohol

diisopropylamine

Downstream raw materials:

(S)-3-(Bis-allyloxy-phosphoryloxy)-2-((S)-2-phenylacetylamino-propionylamino)-propionic acid tert-butyl ester

(2S,3R)-3-(Bis-allyloxy-phosphoryloxy)-2-((S)-2-phenylacetylamino-propionylamino)-butyric acid tert-butyl ester

(S)-3-(Bis-allyloxy-phosphoryloxy)-2-[(S)-2-((S)-2-phenylacetylamino-propionylamino)-propionylamino]-propionic acid tert-butyl ester

Refernces

Synthesis, cleavage, and antifungal activity of a number of novel, water-soluble ester prodrugs of antifungal triazole CS-758

10.1016/j.bmcl.2009.04.135

The research focuses on the synthesis, cleavage, and antifungal activity of novel, water-soluble ester prodrugs of the antifungal triazole CS-758, aimed at developing an injectable antifungal agent for severe deep mycoses in hospitalized patients. The study describes the synthesis of several esters of CS-758, with a particular emphasis on phosphoryl ester 1a, which demonstrated good water solubility and efficient conversion to CS-758 in human liver microsomes and rats. The experiments involved various chemical reactions, including phosphorylation, oxidation, and esterification, utilizing reagents such as diallyl diisopropylphosphoramidite, t-butyl hydroperoxide, and bis(triphenylphosphine)dichloropalladium. The synthesized compounds were analyzed for their water solubility and ability to release CS-758 in vitro using human plasma and liver microsomes, and in vivo by administering the prodrugs to rats and measuring the bioavailability and conversion to CS-758. The antifungal activity of the prodrug 1a was evaluated in a murine systemic Candida albicans infection model, showing comparable or slightly superior effects to orally administered CS-758.