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^*

^*Corresponding author for this work

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

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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.

Original language	English
Pages (from-to)	5622-5626
Number of pages	5
Journal	Organic letters
Volume	22
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.0c01986
Publication status	Published - 17-Jul-2020

Keywords

BRANCHED-CHAIN SUGARS
REGIOSELECTIVE OXIDATION
EVALOSE

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10.1021/acs.orglett.0c01986Licence: CC BY-NC-ND

Stereoselective Protection-Free Modification of 3‑Keto-saccharidesFinal publisher's version, 1.36 MBLicence: CC BY-NC-ND

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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. D. (Contributor) & Minnaard, A. J. (Contributor), University of Groningen, 6-Apr-2020
DOI: 10.5517/ccdc.csd.cc24z1kr
Dataset
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. D. (Contributor) & Minnaard, A. J. (Contributor), University of Groningen, 6-Apr-2020
DOI: 10.5517/ccdc.csd.cc24z1pw
Dataset

Cite this

@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 = "Organic letters",

issn = "1523-7060",

publisher = "AMER CHEMICAL SOC INC",

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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

SN - 1523-7060

VL - 22

SP - 5622

EP - 5626

JO - Organic letters

JF - Organic letters

IS - 14

ER -

Stereoselective Protection-Free Modification of 3-Keto-saccharides

Abstract

Keywords

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Datasets

CCDC 1995084: Experimental Crystal Structure Determination

CCDC 1995088: Experimental Crystal Structure Determination

Cite this