Stereoselective Protection-Free Modification of 3-Keto-saccharides

Nittert Marinus; Nabil Tahiri; Margherita Duca; L M C Marc Mouthaan; Simona Bianca; Marco van den Noort; Bert Poolman; Martin D Witte; Adriaan J Minnaard

doi:10.1021/acs.orglett.0c01986

Stereoselective Protection-Free Modification of 3-Keto-saccharides

Nittert Marinus, Nabil Tahiri, Margherita Duca, L M C Marc Mouthaan, Simona Bianca, Marco van den Noort, Bert Poolman, Martin D Witte, Adriaan J Minnaard^*

^*Bijbehorende auteur voor dit werk

Onderzoeksoutput › Academic › peer review

15 Citaten (Scopus)

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Unprotected 3-keto-saccharides have become readily accessible via site-selective oxidation, but their protection-free functionalization is relatively unexplored. Here we show that protecting groups are obsolete in a variety of stereoselective modifications of our model substrate methyl α-glucopyranoside. This allows the preparation of rare sugars and the installation of click handles and reactive groups. To showcase the applicability of the methodology, maltoheptaose has been converted into a chemical probe, and the rare sugar evalose has been synthesized.

Originele taal-2	English
Pagina's (van-tot)	5622-5626
Aantal pagina's	5
Tijdschrift	Organic letters
Volume	22
Nummer van het tijdschrift	14
DOI's	https://doi.org/10.1021/acs.orglett.0c01986
Status	Published - 17-jul.-2020

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10.1021/acs.orglett.0c01986Licentie: CC BY-NC-ND

Stereoselective Protection-Free Modification of 3‑Keto-saccharidesFinal publisher's version, 1,36 MBLicentie: CC BY-NC-ND

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CCDC 1995088: Experimental Crystal Structure Determination
Marinus, N. (Contributor), Tahiri, N. (Contributor), Duca, M. (Contributor), Mouthaan, M. (Contributor), Bianca, S. (Contributor), van den Noort, M. (Contributor), Poolman, B. (Contributor), Witte, M. (Contributor) & Minnaard, A. (Contributor), University of Groningen, 6-apr.-2020
DOI: 10.5517/ccdc.csd.cc24z1pw
Dataset
CCDC 1995084: Experimental Crystal Structure Determination
Marinus, N. (Contributor), Tahiri, N. (Contributor), Duca, M. (Contributor), Mouthaan, M. (Contributor), Bianca, S. (Contributor), van den Noort, M. (Contributor), Poolman, B. (Contributor), Witte, M. (Contributor) & Minnaard, A. (Contributor), University of Groningen, 6-apr.-2020
DOI: 10.5517/ccdc.csd.cc24z1kr
Dataset

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@article{f84bbb4a98854f889b59a7daa40022cb,

title = "Stereoselective Protection-Free Modification of 3-Keto-saccharides",

abstract = "Unprotected 3-keto-saccharides have become readily accessible via site-selective oxidation, but their protection-free functionalization is relatively unexplored. Here we show that protecting groups are obsolete in a variety of stereoselective modifications of our model substrate methyl α-glucopyranoside. This allows the preparation of rare sugars and the installation of click handles and reactive groups. To showcase the applicability of the methodology, maltoheptaose has been converted into a chemical probe, and the rare sugar evalose has been synthesized.",

keywords = "BRANCHED-CHAIN SUGARS, REGIOSELECTIVE OXIDATION, EVALOSE",

author = "Nittert Marinus and Nabil Tahiri and Margherita Duca and Mouthaan, {L M C Marc} and Simona Bianca and {van den Noort}, Marco and Bert Poolman and Witte, {Martin D} and Minnaard, {Adriaan J}",

year = "2020",

month = jul,

day = "17",

doi = "10.1021/acs.orglett.0c01986",

language = "English",

volume = "22",

pages = "5622--5626",

journal = "Org.Lett.",

issn = "1523-7060",

publisher = "AMER CHEMICAL SOC INC",

number = "14",

}

TY - JOUR

T1 - Stereoselective Protection-Free Modification of 3-Keto-saccharides

AU - Marinus, Nittert

AU - Tahiri, Nabil

AU - Duca, Margherita

AU - Mouthaan, L M C Marc

AU - Bianca, Simona

AU - van den Noort, Marco

AU - Poolman, Bert

AU - Witte, Martin D

AU - Minnaard, Adriaan J

PY - 2020/7/17

Y1 - 2020/7/17

N2 - Unprotected 3-keto-saccharides have become readily accessible via site-selective oxidation, but their protection-free functionalization is relatively unexplored. Here we show that protecting groups are obsolete in a variety of stereoselective modifications of our model substrate methyl α-glucopyranoside. This allows the preparation of rare sugars and the installation of click handles and reactive groups. To showcase the applicability of the methodology, maltoheptaose has been converted into a chemical probe, and the rare sugar evalose has been synthesized.

AB - Unprotected 3-keto-saccharides have become readily accessible via site-selective oxidation, but their protection-free functionalization is relatively unexplored. Here we show that protecting groups are obsolete in a variety of stereoselective modifications of our model substrate methyl α-glucopyranoside. This allows the preparation of rare sugars and the installation of click handles and reactive groups. To showcase the applicability of the methodology, maltoheptaose has been converted into a chemical probe, and the rare sugar evalose has been synthesized.

KW - BRANCHED-CHAIN SUGARS

KW - REGIOSELECTIVE OXIDATION

KW - EVALOSE

U2 - 10.1021/acs.orglett.0c01986

DO - 10.1021/acs.orglett.0c01986

M3 - Article

C2 - 32635733

VL - 22

SP - 5622

EP - 5626

JO - Org.Lett.

JF - Org.Lett.

SN - 1523-7060

IS - 14

ER -

Stereoselective Protection-Free Modification of 3-Keto-saccharides

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Datasets

CCDC 1995088: Experimental Crystal Structure Determination

CCDC 1995084: Experimental Crystal Structure Determination

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