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. Author manuscript; available in PMC: 2014 Dec 1.
Published in final edited form as: European J Org Chem. 2013 Oct 18;2013(36):8162–8173. doi: 10.1002/ejoc.201301089

Table 2.

Preparation of lipid-1-P and the conjugation with GalNAc-1-P forming GalNAc-PP-lipid.

graphic file with name nihms535773u1.jpg
Lipid Geometry Structure R: GalNAc GalNAc-PP-lipids (overall yield)*
undecaprenol 7 Z, 3 E graphic file with name nihms535773t1.jpg
31
59%
heptaprenol 4 Z, 2 E graphic file with name nihms535773t2.jpg
32
36%
pentaprenol 2 Z, 2 E graphic file with name nihms535773t3.jpg
33
49%
(all-Z)-pentaprenol 4 Z, 0 E graphic file with name nihms535773t4.jpg
34
20%
solanesol 0 Z, 8 E graphic file with name nihms535773t5.jpg
35
50%
MS-pentaprenol 1 Z, 2 E graphic file with name nihms535773t6.jpg
36
26%
*

overall yield is based on the polyprenols.