Prodrugs of Vitamin C: The reaction of 1-acyloxyalkyl-1-iodides with Vitamin C 5,6-acetonide

Jennifer McGowan; Nikki Thiele; Kenneth B. Sloan

doi:10.1016/j.tetlet.2015.08.023

Prodrugs of Vitamin C: The reaction of 1-acyloxyalkyl-1-iodides with Vitamin C 5,6-acetonide

Jennifer McGowan
, Nikki Thiele
, Kenneth B. Sloan

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	5441-5444
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	40
DOIs	https://doi.org/10.1016/j.tetlet.2015.08.023
State	Published - Sep 30 2015
Externally published	Yes

Keywords

O-alkylation
Prodrugs
Soft alkyl derivatives
Vitamin C
Vitamin C 5,6-acetonide

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10.1016/j.tetlet.2015.08.023

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title = "Prodrugs of Vitamin C: The reaction of 1-acyloxyalkyl-1-iodides with Vitamin C 5,6-acetonide",

abstract = "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.",

keywords = "O-alkylation, Prodrugs, Soft alkyl derivatives, Vitamin C, Vitamin C 5,6-acetonide",

author = "Jennifer McGowan and Nikki Thiele and Sloan, \{Kenneth B.\}",

year = "2015",

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language = "English",

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journal = "Tetrahedron Letters",

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T2 - The reaction of 1-acyloxyalkyl-1-iodides with Vitamin C 5,6-acetonide

AU - McGowan, Jennifer

AU - Thiele, Nikki

AU - Sloan, Kenneth B.

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 - https://www.scopus.com/pages/publications/84940721725

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 -

Prodrugs of Vitamin C: The reaction of 1-acyloxyalkyl-1-iodides with Vitamin C 5,6-acetonide

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Keywords

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