Synthesis of Macrocyclic Derivatives Containing a Sucrose Unit †

Jarosz, Sławomir; Listkowski, Arkadiusz

doi:10.1081/car-120026473

Cited by 29 publications

(30 citation statements)

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“…Simple sugars can easily be converted into sugar phosphoranes [72,104] or phosphonates, [73,104] which can be used as olefinating agents to provide the α,β-unsaturated enones in good yields (c.f. Figure 11, Section 4.2).…”

Section: Synthesis Of Bicyclo[440]decenesmentioning

confidence: 99%

“…[70] Over recent years we have proposed a general methodology for the preparation of higher-carbon sugars by coupling of two sugar subunits. [71] The precursor 33 is readily obtained from sugar phosphoranes [72] 31, phosphonates [73] 32, or vinyltin derivatives of monosaccharides [74] 34 ( Figure 11). Another class of higher sugar precursors -homoallylic alcohols flanked at both ends with sugar moieties (e.g., 37 in Figure 12) -was recently prepared by us in a boron trifluoride-catalyzed addition of sugar allyltins to sugar aldehydes.…”

Section: Synthesis Of Higher-carbon Sugars From Allyltin Compoundsmentioning

confidence: 99%

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Sugar Allyltin Compounds: Preparation and Application in Organic Synthesis

Jarosz

Gaweł

2005

Eur J Org Chem

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General methodology for the preparation of allyltin derivatives is reported, with special attention paid to sugar allyltins. Typical procedures affording such organometallics involve the conversion of partially protected hexoses or pentoses (Sug–CH2OH) into homologated allylic alcohols (Sug–CH=CH–CH2OH), which are further transformed into the primary or secondary sugar allyltin derivatives of the general formula Sug–CH=CH–CH2SnR3, (E)/(Z) ratio ≈ 5:1, or Sug–CH*(SnR3)–CH=CH2 (single isomer with the (S)‐configuration at the newly created chiral center*). Controlled Lewis acid‐induced fragmentation of these hexose‐derived organometallics provides highly oxygenated dienoaldehydes with the (E) geometry across the internal double bond: CH2=CH–CH=CH–[CH(OR)]3–CHO. The (Z)‐dienoaldehydes are also available by thermal fragmentation of the secondary sugar allyltins. Both these synthons ((E) and (Z)) can be further converted into highly functionalized derivatives of bicyclo[4.3.0]nonene and bicyclo[4.4.0]decene. Stereochemical aspects of reactions between sugar allyltins and sugar aldehydes (in the presence of Lewis acids or under high pressure) are also discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Section: Synthesis Of Bicyclo[440]decenesmentioning

confidence: 99%

Section: Synthesis Of Higher-carbon Sugars From Allyltin Compoundsmentioning

confidence: 99%

Sugar Allyltin Compounds: Preparation and Application in Organic Synthesis

Jarosz

Gaweł

2005

Eur J Org Chem

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“…of bulky pivaloyl chloride preferentially afforded the 6Ј-protected derivative 65, although in low yield (30%). [62] If the hydroxy groups in 60 are activated with tri-n-butyltin oxide, the yield of 65 increases to 45%. However, small amounts of the 6,6Ј-diprotected derivative 65a are isolated in both cases.…”

Section: Differentiation Of the Primary Hydroxy Groups In Penta-o-benmentioning

confidence: 99%

“…However, small amounts of the 6,6Ј-diprotected derivative 65a are isolated in both cases. [62] From these experiments, the following reactivity pattern (towards acylation) can be assigned to the primary hydroxy groups in 2,3,4,3Ј,4Ј-penta-O-benzylsucrose (60): 6Ј-OH Ͼ 6-OH ϾϾ 1Ј-OH. [62] This selectivity is different to that observed for free sucrose activated with tin species, in which the 6-OH is preferentially protected.…”

Section: Differentiation Of the Primary Hydroxy Groups In Penta-o-benmentioning

confidence: 99%

“…[62] From these experiments, the following reactivity pattern (towards acylation) can be assigned to the primary hydroxy groups in 2,3,4,3Ј,4Ј-penta-O-benzylsucrose (60): 6Ј-OH Ͼ 6-OH ϾϾ 1Ј-OH. [62] This selectivity is different to that observed for free sucrose activated with tin species, in which the 6-OH is preferentially protected. [28,29] Chlorination (Ph 3 P/CCl 4 ) of 60 is not as selective as for free sucrose.…”

Section: Differentiation Of the Primary Hydroxy Groups In Penta-o-benmentioning

confidence: 99%

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Regio- and Stereoselective Transformations of Sucrose at the Terminal Positions

Jarosz

Mach

2002

Eur. J. Org. Chem.

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Synthesis of Sugar-Derived 2′- and 3′-Substituted Furans and Their Application in Diels−Alder Reactions

et al. 2001

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A convenient synthesis of 2Ј-and 3Ј-furyl sugars in which the furan and the sugar parts are directly connected is presented. The key step comprises HF·py-induced cyclization of α,β-unsaturated carbonyl compounds (ketones or aldehydes) possessing terminal hydroxymethylene groups protected as TBDPS ethers. Treatment of such furan derivatives with N-Preceding communication: Ref. [1] [a] 2955 phenylmaleimide under high-pressure conditions (11 kbar) produces the corresponding [4+2] adducts, with the endo forms predominating. At p = 1 atm and T = 20°C, however, the exo isomers are formed as the main products. The [4+2] adducts undergo retro Diels−Alder reactions at elevated temperatures at atmospheric pressure.

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Synthesis of Macrocyclic Derivatives Containing a Sucrose Unit †

Cited by 29 publications

References 0 publications

Sugar Allyltin Compounds: Preparation and Application in Organic Synthesis

Sugar Allyltin Compounds: Preparation and Application in Organic Synthesis

Regio- and Stereoselective Transformations of Sucrose at the Terminal Positions

Synthesis of Sugar-Derived 2′- and 3′-Substituted Furans and Their Application in Diels−Alder Reactions

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