TY - JOUR
T1 - Prodrugs of Vitamin C
T2 - The reaction of 1-acyloxyalkyl-1-iodides with Vitamin C 5,6-acetonide
AU - McGowan, Jennifer
AU - Thiele, Nikki
AU - Sloan, Kenneth B.
N1 - Publisher Copyright:
© 2015 Elsevier Ltd.All rights reserved.
PY - 2015/9/30
Y1 - 2015/9/30
N2 - The reaction of 2 equiv of 1-acyloxyalkyl-1-iodides with vitamin C 5,6-acetonide gave mixtures of products that were O-alkylated on the 3-position and either O-alkylated, 7, or O-acylated, 8, on the 2-position. The 8 products comprised the majority of the mixtures: 56:54 to 94:6. The 3-alkylated-2-acylated prodrugs, 8, hydrolyzed to vitamin C 5,6-acetonide chemically at pH 7.4 with half-lives of 6-12 h.
AB - The reaction of 2 equiv of 1-acyloxyalkyl-1-iodides with vitamin C 5,6-acetonide gave mixtures of products that were O-alkylated on the 3-position and either O-alkylated, 7, or O-acylated, 8, on the 2-position. The 8 products comprised the majority of the mixtures: 56:54 to 94:6. The 3-alkylated-2-acylated prodrugs, 8, hydrolyzed to vitamin C 5,6-acetonide chemically at pH 7.4 with half-lives of 6-12 h.
KW - O-alkylation
KW - Prodrugs
KW - Soft alkyl derivatives
KW - Vitamin C
KW - Vitamin C 5,6-acetonide
UR - http://www.scopus.com/inward/record.url?scp=84940721725&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2015.08.023
DO - 10.1016/j.tetlet.2015.08.023
M3 - Article
AN - SCOPUS:84940721725
SN - 0040-4039
VL - 56
SP - 5441
EP - 5444
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 40
ER -