Sequential removal of the benzyl-type protecting groups PMB and NAP by oxidative cleavage using CAN and DDQ

Joseph A. Wright; Jiangang Yu; Jonathan B. Spencer

doi:10.1016/S0040-4039(01)00563-9

Sequential removal of the benzyl-type protecting groups PMB and NAP by oxidative cleavage using CAN and DDQ

Joseph A. Wright, Jiangang Yu, Jonathan B. Spencer

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

93 Citations (Scopus)

Abstract

The selective cleavage of the PMB (4-methoxybenzyl) group in the presence of the NAP (2-naphthylmethyl) group was achieved using CAN with a range of mono-saccharides. The NAP group can then be removed selectively in the presence of a benzyl group using DDQ. This provides a strategy for sequential deprotection of hydroxyl groups.

Original language	English
Pages (from-to)	4033-4036
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	24
DOIs	https://doi.org/10.1016/S0040-4039(01)00563-9
Publication status	Published - 2001

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10.1016/S0040-4039(01)00563-9

Cite this

@article{fed4462a1eb54b038a2a3304b034664c,

title = "Sequential removal of the benzyl-type protecting groups PMB and NAP by oxidative cleavage using CAN and DDQ",

abstract = "The selective cleavage of the PMB (4-methoxybenzyl) group in the presence of the NAP (2-naphthylmethyl) group was achieved using CAN with a range of mono-saccharides. The NAP group can then be removed selectively in the presence of a benzyl group using DDQ. This provides a strategy for sequential deprotection of hydroxyl groups.",

author = "Wright, {Joseph A.} and Jiangang Yu and Spencer, {Jonathan B.}",

year = "2001",

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TY - JOUR

T1 - Sequential removal of the benzyl-type protecting groups PMB and NAP by oxidative cleavage using CAN and DDQ

AU - Wright, Joseph A.

AU - Yu, Jiangang

AU - Spencer, Jonathan B.

PY - 2001

Y1 - 2001

N2 - The selective cleavage of the PMB (4-methoxybenzyl) group in the presence of the NAP (2-naphthylmethyl) group was achieved using CAN with a range of mono-saccharides. The NAP group can then be removed selectively in the presence of a benzyl group using DDQ. This provides a strategy for sequential deprotection of hydroxyl groups.

AB - The selective cleavage of the PMB (4-methoxybenzyl) group in the presence of the NAP (2-naphthylmethyl) group was achieved using CAN with a range of mono-saccharides. The NAP group can then be removed selectively in the presence of a benzyl group using DDQ. This provides a strategy for sequential deprotection of hydroxyl groups.

U2 - 10.1016/S0040-4039(01)00563-9

DO - 10.1016/S0040-4039(01)00563-9

M3 - Article

VL - 42

SP - 4033

EP - 4036

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 24

ER -