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Catalyst-Controlled, Regioselective Reactions of Carbohydrate Derivatives

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Site-Selective Catalysis

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 372))

Abstract

Carbohydrates generally possess multiple hydroxyl groups of similar reactivity, and selective monofunctionalization is often difficult. Catalysis provides a versatile and potentially general solution to this problem. This chapter provides an overview of catalyst-controlled methods for the regioselective activation of carbohydrate derivatives. The catalysts discussed include organocatalysts (Lewis bases, Brønsted acids/bases, and others) as well as those based on main group and transition metal elements.

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Abbreviations

[TMPhA]+ :

Trimethylphenylammonium

Ac:

Acetyl

acac:

Acetylacetonate

AIBN:

Azobis(isobutyronitrile)

Ala:

Alanine

Alloc:

Allyloxycarbonyl

Ar:

Aryl

BINOL:

2,2′-Dihydroxy-1,1′-binaphthyl

Bn:

Benzyl

Boc:

tert-Butoxycarbonyl

BOX:

Bis(oxazoline)

Bu:

Butyl

Bz:

Benzoyl

Cbz:

Benzyloxycarbonyl

COD:

Cyclooctadiene

DCB:

2,6-Dichloro-1,4-benzoquinone

DMAc:

N,N-Dimethylacetamide

DMAP:

4-(Dimethylamino)pyridine

DME:

1,2-Dimethoxyethane

DMF:

Dimethylformamide

DPG:

Directing–protecting group

EPPS:

4-(2-Hydroxyethyl)-1-piperazinepropanesulfonic acid

Et:

Ethyl

Gal:

Galactose

Glc:

Glucose

GlcNAc:

N-Acetylglucosamine

i-Pr:

Isopropyl

M:

Mole per liter

Man:

Mannose

Me:

Methyl

MES:

2-(N-Morpholino)ethanesulfonic acid

Ms:

Methanesulfonyl

MS:

Molecular sieves

NMR:

Nuclear magnetic resonance

PEMP:

1,2,2,6,6-Pentamethylpiperidine

Ph:

Phenyl

Phe:

Phenylalanine

PMH:

Ï€-Methylhistidine

PMP:

4-Methoxyphenyl

PPY:

4-Pyrrolidinopyridine

Pr:

Propyl

T :

Temperature

TBDPS:

tert-Butyldiphenylsilyl

TBS:

tert-Butyldimethylsilyl

t-Bu:

tert-Butyl

TES:

Triethylsilyl

Tf:

Trifluoromethanesulfonyl (triflyl)

THF:

Tetrahydrofuran

THP:

Tetrahydropyranyl

TMEDA:

N,N,N′,N′-Tetramethylethylenediamine

Trp:

Tryptophan

Trt:

Triphenylmethyl

Ts:

Tosyl, 4-toluenesulfonyl

U:

Uracil

X:

Generic leaving group

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  1. Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, Canada, M5S 3H6

    Mark S. Taylor

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  1. Institute for Chemical Research Kyoto University, Kyoto, Japan

    Takeo Kawabata

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Taylor, M.S. (2015). Catalyst-Controlled, Regioselective Reactions of Carbohydrate Derivatives. In: Kawabata, T. (eds) Site-Selective Catalysis. Topics in Current Chemistry, vol 372. Springer, Cham. https://doi.org/10.1007/128_2015_656

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