40733-25-3

Basic information

• Product Name: thymidine 5'-O-pivaloate
• Synonyms: thymidine 5'-O-pivaloate
• CAS NO: 40733-25-3
• Molecular Formula: C₁₅H₂₂N₂O₆
• Molecular Weight: 326.345
• Mol File: 40733-25-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.278g/cm³
• Refractive Index: 1.532
• CAS DataBase Reference: thymidine 5'-O-pivaloate(CAS DataBase Reference)
• NIST Chemistry Reference: thymidine 5'-O-pivaloate(40733-25-3)
• EPA Substance Registry System: thymidine 5'-O-pivaloate(40733-25-3)

Safety Data

• Hazardous Substances Data: 40733-25-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H22N2O6/c1-8-6-17(14(21)16-12(8)19)11-5-9(18)10(23-11)7-22-13(20)15(2,3)4/h6,9-11,18H,5,7H2,1-4H3,(H,16,19,21)

Upstream product

• 3282-30-2 pivaloyl chloride 
• 50-89-5 thymidine 
• 1228354-89-9 N₃,5'-O-bis(trimethylacetyl)thymidine 

Downstream Products

• 1228354-90-2 3'-O-(4,4'-diemthoxytrityl)-5'-O-(trimethylacetyl)thymidine 
• 13084-61-2 3'-O-(4-methoxytriphenylmethyl)thymidine 
• 132062-93-2 3-N,3'-O-bis(benzyloxymethyl)-2'-deoxy-5'-O-(p-toluenosulfonyl)thymidine 
• 132062-87-4 3-N,3'-O-bis(benzylomethyl)-2'-deoxy-5'-O-phosphonomethylthymidine diethyl ester 
• 132062-81-8 3-N,3'-O-bis(benzyloxymethyl)-2'-deoxy-5'-O-pivaloylthymidine 
• 132063-01-5 3-N,3'-O-bis(benzyloxymethyl)-2'-deoxythymidine 
• 120826-44-0 2',3'-didehydro-2',3'-dideoxy-5-methylcytidine 
• 107036-56-6 2',3'-dideoxy-5-methylcytidine 
• 357610-49-2 2,2-Dimethyl-propionic acid (2R,3S,5R)-3-[{2-benzoyl-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-oxo-butoxy}-(2-methoxy-ethoxy)-phosphoryloxy]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 357610-48-1 2,2-Dimethyl-propionic acid (2R,3S,5R)-3-[{3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-2,2-dicyano-propoxy}-(2-methoxy-ethoxy)-phosphoryloxy]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 357610-47-0 3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-2-cyano-2-[[(2R,3S,5R)-2-(2,2-dimethyl-propionyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-(2-methoxy-ethoxy)-phosphoryloxymethyl]-propionic acid methyl ester 
• 357610-46-9 2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-[[(2R,3S,5R)-2-(2,2-dimethyl-propionyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-(2-methoxy-ethoxy)-phosphoryloxymethyl]-malonic acid diethyl ester 
• 132062-80-7 3-N-benzylomethyl-2'-deoxy-5'-O-pivaloylthymidine 

Relevant articles and documents

LINKAGE MODIFIED OLIGOMERIC COMPOUNDS

The present invention provides gapped oligomeric compounds comprising from 1 to about 3 internucleoside linkages having one of formulas I to XVI. In certain embodiments, inclusion of from 1 to about 3 internucleoside linkages of one of formulas I to XVI,

4-Acetylthio-2,2-dimethyl-3-oxobutyl group as an esterase- And thermo-labile protecting group for oligomeric phosphodiesters

(4-Acetylthio-2,2-dimethyl-3-oxobutyl)-protected oligomeric phosphodiesters 1 and 2 were synthesized and removal of the protecting groups in the presence and absence of hog liver esterase was followed at pH 7.5 and 37 °C. Phosphotriesters 1 and 2 were successfully converted into the desired fully deprotected phosphodiesters 3 and 4, respectively. Some cleavage of internucleosidic P-O bonds took place, which reduced the yield of 3 and 4. Non-enzymatic removal of the protecting group was only modestly retarded by accumulation of negative charge on the molecule. With 1, the half-lives for the departure of the first and second protecting groups were 7.8 and 10.7 h, respectively, and with 2, 6.2 and 7.2 h, respectively. After 4 d, 70% of both starting materials 1 and 2 were converted into the unprotected phosphodiester. The presence of hog liver esterase (2.6 units mL-1) resulted in fast removal of the first protecting group (τ1/2 2.7 min and 36 min with 1 and 2, respectively), but the appearance of fully deprotected 3 and 4 was accelerated only by a factor of 2, consistent with dramatic retardation of the enzymatic reaction upon accumulation of the negative charge.

A convenient protection for 4-oxopyrimidine moieties in nucleosides by the pivaloyl group

Application of the pivaloyl group as a protection for the N3 position of thymidine and uridine was investigated. Pivaloylation of thymidine is a very rapid reaction proceeding under mild conditions with excellent regioselectivity for sugar or thymine moiety, depending on the amines used. Several pivaloylated thymidine derivatives were obtained by treatment of unprotected thymidine with pivaloyl chloride under various experimental conditions. Stability of the N3-pivaloyl protecting group under basic and acidic conditions was evaluated and the conditions for its selective removal were found.