ChemicalBook CAS DataBase List 1-(3-beta-Azido-2,3-dideoxy-5-O-trityl-beta-D-threopenta-furanosyl)thyMine

1-(3-beta-Azido-2,3-dideoxy-5-O-trityl-beta-D-threopenta-furanosyl)thyMine synthesis

6synthesis methods

Product Name:1-(3-beta-Azido-2,3-dideoxy-5-O-trityl-beta-D-threopenta-furanosyl)thyMine
CAS Number:66503-47-7
Molecular formula:C29H27N5O4
Molecular Weight:509.5558

2,5-Methano-5H,9H-pyrimido[2,1-b][1,5,3]dioxazepin-9-one, 2,3,10,10a-tetrahydro-8-methyl-3-[(triphenylmethoxy)methyl]-, (2R,3R,5R)-

909256-85-5
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1-(3-beta-Azido-2,3-dideoxy-5-O-trityl-beta-D-threopenta-furanosyl)thyMine

66503-47-7
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Yield:66503-47-7 96.3 %

Reaction Conditions:

with sodium azide;phosphoric acid in dimethyl sulfoxide at 100;Temperature;

Steps:

1-2; 1 Example 1

In the pre-reaction bottle, add 75.0g (1.0eq) of the formula II compound (prepared with reference to US5124442 preparation method), 19.9g (1.9eq) sodium azide,150ml dimethyl sulfoxide solvent, 7.5g 85% phosphoric acid solution,The reaction mixture was heated to 100°C and stirred for 10-15 minutes.After most of the solids are dissolved, keep the system warm and set aside;Raise the temperature of the heating medium oil bath of the tubular reactor to 155-160°C,Peristaltic pump set flow rate 1.5ml/min,The pre-prepared reaction mixture was fed to the tubular reactor through a peristaltic pump,At the same time, the pump head and tube of the peristaltic pump need to be kept warm at 90-100°C;Run for about 15 minutes,Receive the effluent with a receiving bottle, and the effluent is the reaction solution containing the compound of formula I.Pump the reaction solution containing the compound of formula I into a reaction flask with water added, stir for 0.5 to 1 hour, filter, wash the filter cake with water,The filter cake was dried in a vacuum oven to constant weight,Obtain 78.6g of compound of formula I (yield 96.3%, purity 96.7%)

References:

CN115368424,2022,A Location in patent:Paragraph 0012; 0048-0057

42214-24-4 Synthesis