1-Naphthylmethyl and 1-naphthylmethoxymethyl protecting groups

New members of the benzyl- and benzyloxymethyl-type family

Takuya Sato, Yohei Joh, Tohru Oishi, Kohei Torikai

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

1-Naphthylmethyl (NAPI) and 1-naphthylmethoxymethyl (NAPOMI) protecting groups were developed as new members of the benzyl- and benzyloxymethyl-type family. NAPI and NAPOMI can be introduced under conventional conditions, such as NAPIBr/NaH/room temperature (rt), or NAPOMICl/i-Pr2EtN/rt. They can also be removed under conventional conditions, e.g., by dichlorodicyanobenzoquinone (DDQ)- or ceric ammonium nitrate (CAN)-mediated oxidation, or by hydrogenolysis. The specific advantages of these new protecting groups are: i) a less costly synthesis of NAPOMICl compared to NAPOMIICl, ii) the possibility to remove NAPOMII selectively in the presence of NAPOMI by DDQ-mediated oxidation, and iii) the compatibility with strong acids even in the presence of hard nucleophiles.

Original languageEnglish
Pages (from-to)2178-2181
Number of pages4
JournalTetrahedron Letters
Volume58
Issue number23
DOIs
Publication statusPublished - Jan 1 2017

Fingerprint

Oxidation
Hydrogenolysis
Nucleophiles
Temperature
Acids
dichlorodicyanobenzoquinone
ceric ammonium nitrate

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

1-Naphthylmethyl and 1-naphthylmethoxymethyl protecting groups : New members of the benzyl- and benzyloxymethyl-type family. / Sato, Takuya; Joh, Yohei; Oishi, Tohru; Torikai, Kohei.

In: Tetrahedron Letters, Vol. 58, No. 23, 01.01.2017, p. 2178-2181.

Research output: Contribution to journalArticle

@article{24bba7380f8e4f9fae71681491cfb3b4,
title = "1-Naphthylmethyl and 1-naphthylmethoxymethyl protecting groups: New members of the benzyl- and benzyloxymethyl-type family",
abstract = "1-Naphthylmethyl (NAPI) and 1-naphthylmethoxymethyl (NAPOMI) protecting groups were developed as new members of the benzyl- and benzyloxymethyl-type family. NAPI and NAPOMI can be introduced under conventional conditions, such as NAPIBr/NaH/room temperature (rt), or NAPOMICl/i-Pr2EtN/rt. They can also be removed under conventional conditions, e.g., by dichlorodicyanobenzoquinone (DDQ)- or ceric ammonium nitrate (CAN)-mediated oxidation, or by hydrogenolysis. The specific advantages of these new protecting groups are: i) a less costly synthesis of NAPOMICl compared to NAPOMIICl, ii) the possibility to remove NAPOMII selectively in the presence of NAPOMI by DDQ-mediated oxidation, and iii) the compatibility with strong acids even in the presence of hard nucleophiles.",
author = "Takuya Sato and Yohei Joh and Tohru Oishi and Kohei Torikai",
year = "2017",
month = "1",
day = "1",
doi = "10.1016/j.tetlet.2017.04.046",
language = "English",
volume = "58",
pages = "2178--2181",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "23",

}

TY - JOUR

T1 - 1-Naphthylmethyl and 1-naphthylmethoxymethyl protecting groups

T2 - New members of the benzyl- and benzyloxymethyl-type family

AU - Sato, Takuya

AU - Joh, Yohei

AU - Oishi, Tohru

AU - Torikai, Kohei

PY - 2017/1/1

Y1 - 2017/1/1

N2 - 1-Naphthylmethyl (NAPI) and 1-naphthylmethoxymethyl (NAPOMI) protecting groups were developed as new members of the benzyl- and benzyloxymethyl-type family. NAPI and NAPOMI can be introduced under conventional conditions, such as NAPIBr/NaH/room temperature (rt), or NAPOMICl/i-Pr2EtN/rt. They can also be removed under conventional conditions, e.g., by dichlorodicyanobenzoquinone (DDQ)- or ceric ammonium nitrate (CAN)-mediated oxidation, or by hydrogenolysis. The specific advantages of these new protecting groups are: i) a less costly synthesis of NAPOMICl compared to NAPOMIICl, ii) the possibility to remove NAPOMII selectively in the presence of NAPOMI by DDQ-mediated oxidation, and iii) the compatibility with strong acids even in the presence of hard nucleophiles.

AB - 1-Naphthylmethyl (NAPI) and 1-naphthylmethoxymethyl (NAPOMI) protecting groups were developed as new members of the benzyl- and benzyloxymethyl-type family. NAPI and NAPOMI can be introduced under conventional conditions, such as NAPIBr/NaH/room temperature (rt), or NAPOMICl/i-Pr2EtN/rt. They can also be removed under conventional conditions, e.g., by dichlorodicyanobenzoquinone (DDQ)- or ceric ammonium nitrate (CAN)-mediated oxidation, or by hydrogenolysis. The specific advantages of these new protecting groups are: i) a less costly synthesis of NAPOMICl compared to NAPOMIICl, ii) the possibility to remove NAPOMII selectively in the presence of NAPOMI by DDQ-mediated oxidation, and iii) the compatibility with strong acids even in the presence of hard nucleophiles.

UR - http://www.scopus.com/inward/record.url?scp=85018989380&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85018989380&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2017.04.046

DO - 10.1016/j.tetlet.2017.04.046

M3 - Article

VL - 58

SP - 2178

EP - 2181

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 23

ER -