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De novo Synthesis of Monosaccharides

  • Reference work entry
Glycoscience

Abstract

Recent approaches to asymmetric total synthesis of monosaccharides and derivatives are reviewed. They imply biochemical methods or chemical methods, or combinations of both. Aldoses, alditols, deoxysugars, aminodeoxymonosaccharides, and their analogues are considered, including aza- and thiosugars (with nitrogen and sulfur in the pyranose or furanose ring). Most common monosaccharides have three to six carbon‐chains, but examples of long-chain and branched-chain carbohydrates will also be described. Organization of the review is based on the synthetic methodology rather than on the types of targeted sugar, starting with aldolase‐catalyzed aldol reactions of achiral precursors, and the now popular amino-acid‐catalyzed aldol and Mannich reactions. Chain elongations of small aldose derivatives with one, two, three, or four carbons remain very useful approaches as they allow one to reach a large structural and stereochemical diversity. Other methods apply Diels–Alder or hetero-Diels–Alder additions. Enantiomerically pure monosaccharides have been derived from achiral alkene, diene, and triene derivatives. Almost any targeted natural or non-natural sugar and derivative can be obtained in a few synthetic steps from inexpensive starting materials.

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Abbreviations

9-BBN:

9-borabicyclo[3.3.1]nonane

Ac:

MeCO

AIBN:

azoisobutyronitrile

Bn:

benzyl

Boc:

(t-Bu)OCO

BOM:

PhCH2OCH2

Bu:

n-butyl

Bz:

PhCO

Cbz:

BnOCO

CDI:

carbonyldiimidazole

Co(II)(salen)2 :

salcomine: N,N′-bis(salicylidene)ethylenediaminocobalt (II)

RAMP:

(R)‑(+)‑amino-2-(methoxymethyl)pyrrolidine

dba:

dibenzylideneacetone

DBN:

1,5-diazabicyclo[4.3.0]non-5-ene

DBU:

1,8-diazabicyclo[5.4.0]undec-7-ene

DDQ:

dichlorodicyanobenzoquinone

DERA:

2-deoxyribose-5-phosphate aldolase

DFT:

density functional theory

DHA:

dihydroxyacetone

DHAP:

dihydroxyacetone phosphate

DIBAL-H:

(i-Bu)2AlH

DMAP:

4-(dimethylamino)pyridine

DMF:

dimethylformamide

DMSO:

dimethylsulfoxide

DMTC:

5,5-dimethyl thiazolidinium-4-carboxylate

dr:

diastereomeric ratio

ee:

enantiomeric excess

FDP:

fructose-1,6-diphosphate

fod:

6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedienoate

Grubbs I:

[(cyclohexyl)3P]2Ru(Cl)2CHPh

Grubbs II:

[(cyclohexyl)3P][1,3‑(2,4,6‑trimethylphenyl)‐1,3‑diazolidinylidene]Ru(Cl)2CHPh

hfc:

3-(heptafluoropropylhydroxymethylene)-(+)‑camphorate

HMPA:

hexamethyl phosphortriamide

i-Pr:

isopropyl

LDA:

lithium diisopropylamide

K-Selectride:

KB[CH(Me)Et]3H

l-(+)‑DIPT:

l-(+)‑diisopropyl tartrate

l‑KDO:

3-deoxy-l-manno-oct-2-ulosonic acid

l‑Selectride:

LiB[CH(Me)Et]3H

LTMP:

lithium 2,2,6,6-tetramethylpiperidine

mCPBA:

meta-chloroperbenzoic acid

MEM:

MeOCH2CH2OCH2

Ms:

methanesulfonyl (MeSO2)

“naked aza-sugar”:

enantiomerically pure 7-oxa-bicyclo[2.2.1]hept-2-ene derivative

“naked sugar”:

enantiomerically pure 7-aza-bicyclo[2.2.2]hept-2-ene derivative

NCS:

N‑chlorosuccinimide

NMO:

N‑methylmorpholine N‑oxide

NMP:

N‑methylpyrrolidone

PEP:

phosphoreol pyruvate

Piv:

pivaloyl (t-BuCO)

PMBz:

4-MeOC6H4CO

py:

pyridine

RADO(Et)OH:

(1R,7R)-3-ethyl-2-oxo-3-aza-6,8-dioxabicyclo[3.2.1]octane‐7‐exo‐carboxylic acid

RAMA:

rabbit muscle aldolase

Red-Al:

(MeOCH2CH2O)2AlH2Na

SADO(Et)OH:

(1S,7S)-3-ethyl-2-oxo-3-aza-6,8-dioxabicyclo[3.2.1]octane‐7‐exo‐carboxylic acid

SAMP:

(S)‑(−)‑amino-2-(methoxymethyl)pyrrolidine

Sia2BH:

(Me2CHCHMe)2BH

S-Pro:

l-proline

TBS:

(t-Bu)Me2Si

t-Bu:

tert-butyl

TES:

Et3Si

Tf:

triflyl (CF3SO2)

THF:

tetrahydrofurane

THP:

2-tetrahydropyranyl

TIPS:

(i-Pr)3Si

TMS:

Me3Si

Ts:

para-toluenesulfonyl (4-MeC6H4SO2)

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Author information

Authors and Affiliations

  1. Laboratoire de glycochimie et de synthèse asymétrique, Ecole Polytechnique Fédérale de Lausanne (EPFL), BCH, 1015, Lausanne-Dorigny, Switzerland

    Pierre Vogel

  2. Departamento de Química Orgánica, Universidad de Sevilla, 41071, Sevilla, Spain

    Inmaculada Robina

Authors
  1. Pierre Vogel
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  2. Inmaculada Robina
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Editors and Affiliations

  1. Natural Products and Glycotechnology Research Institute Inc., North Caroline State University, 4118 Swarthmore Road, Durham, NC, 27707, USA

    Bertram O. Fraser-Reid Prof. Dr.

  2. University Graduate School of Science and Engineering, 3-4-1 Ohkubo, Shinjuku, Tokyo, Japan

    Kuniaki Tatsuta Prof. Dr.

  3. Faculty of ScienceDepartment of Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany

    Joachim Thiem Prof. Dr.

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Vogel, P., Robina, I. (2008). De novo Synthesis of Monosaccharides. In: Fraser-Reid, B.O., Tatsuta, K., Thiem, J. (eds) Glycoscience. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-30429-6_20

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