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67746-43-4 - Dibenzyl diethylphosphoramidite, 90+% - DDP - B25619 - Alfa Aesar

B25619 Dibenzyl diethylphosphoramidite, 90+%

CAS Number
67746-43-4
Synonyms
DDP

Size Price ($) Quantity Availability
1g 76.30
5g 259.00
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Dibenzyl diethylphosphoramidite, 90+%

MDL
MFCD00191987

Chemical Properties

Formula
C18H24NO2P
Formula Weight
317.37
Flash Point
73°(163°F)
Density
1.060
Refractive Index
1.5450
Sensitivity
Moisture Sensitive
Solubility
Soluble in chloroform.

Applications

Dibenzyl N,N-diethylphosphoramidite may be used as phosphitylating reagent in the synthesis of glycosyl phosphites and phosphates, in the preparation of 6-dibenzylphosphate-1,3,5-tri-O-PMB-myo-inositol, for phosphorylating the alcohols.

Notes

Store in cool, dry place in a well sealed container. Store away from oxidizing agents.

Literature References

Mui Mui Sim; Hirosato Kondo; Chi Huey Wong. Synthesis of dibenzyl glycosyl phosphites using dibenzyl N, N-diethylphosphoramidite as phosphitylating reagent: an effective route to glycosyl phosphates, nucleotides, and glycosides. J. Am. Chem. Soc. 1993, 115 (6), 2260-2267.

Peter A Jordan; Katherine J Kayser-Bricker; Scott J Miller. Asymmetric phosphorylation through catalytic P(III) phosphoramidite transfer: enantioselective synthesis of D-myo-inositol-6-phosphate. PNAS. 2010, 107 (48), 20620-20624.

Phosphitylating agent which reacts with an alcohol under mild conditions. Subsequent oxidation, e.g. with hydrogen peroxide, followed by hydrogenolysis of the benzyl groups, affords the alkyl phosphate: Tetrahedron, 47, 2643 (1991); J. Org. Chem., 59, 7182 (1994). This sequence provides a convenient route to glycosyl phosphates via the glycosyl phosphites: J. Am. Chem. Soc. 115, 2260 (1993).

GHS Hazard and Precautionary Statements

Hazard Statements: H227-H315-H319-H335

Combustible liquid. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P210u-P261-P280a-P280a-P305+P351+P338-P304+P340-P312a-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Harmonized Tariff Code
2931.39
TSCA
No

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