Nucleoside, V. 6‐Dimethylamino‐purin‐Nucleoside der 3‐Amino‐3‐desoxy‐β‐<scp>D</scp>‐glucose, ‐mannose und ‐galaktose

Lichtenthaler, Frieder W.; Albrecht, Hans

doi:10.1002/cber.19691020331

Chem. Ber.

1969

DOI: 10.1002/cber.19691020331

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Nucleoside, V. 6‐Dimethylamino‐purin‐Nucleoside der 3‐Amino‐3‐desoxy‐β‐D‐glucose, ‐mannose und ‐galaktose

Frieder W. Lichtenthaler

Hans Albrecht

Abstract: Perjodat-Oxydation von 6-Dimethylamino-9-[P-~-ribofuranosyl]-purin (4) und anschlieRende Nitromethan-Cyclisierung liefert ein Gemisch von 3'-Nitro-hexosyl-dimethylaminopurinen (75 %), das durch fraktionierte Kristallisation in die gluco-, manno-und galakto-Isomeren

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Cited by 9 publications

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“…The nitroaldol 8a was converted into the amine 12 by catalytic hydrogenation. 13 Cyclization of 12 with the Appel reagent (Ph 3 P, CCl 4 , Et 3 N), 14 followed by ion exchange chromatography and hydrochloric acid treatment, afforded the d-iminomannitol 1 in 74% yield after conversion into the hydrochloride (Scheme 3); the overall yield from d-mannitol was 10% (seven steps). Starting from 9a, the d-gulo isomer 15 was accessible likewise, as confirmed by crystal structure analysis.…”

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confidence: 99%

Synthesis of iminopolyols via Henry reaction: a short route to the α-manno- sidase inhibitor 1,4-dideoxy-1,4-imino-D-mannitol and to amino analogues†,1

Kieß¹,

Poggendorf²,

Jäger³

et al. 1998

Chem. Commun.

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confidence: 99%

Synthesis of iminopolyols via Henry reaction: a short route to the α-manno- sidase inhibitor 1,4-dideoxy-1,4-imino-D-mannitol and to amino analogues†,1

Kieß¹,

Poggendorf²,

Jäger³

et al. 1998

Chem. Commun.

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Synthese von D‐ und L‐2‐Amino‐2‐desoxyarabinose sowie von D‐ und L‐1,4‐Didesoxy‐1,4‐iminolyxit durch (C₂ + C₃)‐Nitroaldol‐Addition mit 2‐O‐Benzylglycerinaldehyd

Wehner¹,

Jäger²

1990

Angewandte Chemie

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Mit der hochstereoselektiven Nitroaldol‐Addition von Nitroacetaldehyd‐diethylacetal 1 und 2‐O‐Benzylglycerinaldehyd 2 zu nur zwei der vier möglichen Diastereomere von 3 im Verhältnis 88:12 wurde ein ergiebiger Zugang zu beiden Enantiomeren von 2‐Arabinosamin sowie zu 1,4‐Didesoxy‐1,4‐iminolyxit (Glucosidase‐Inhibitor) eröffnet. Die Gesamtausbeute über acht Stufen zum Lyxit beträgt 17%.

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Synthesis of D‐ and L‐2‐Amino‐2‐deoxyarabinose and 1,4‐Dideoxy‐1,4‐iminolyxitol by (C₂ + C₃)‐Nitroaldol Addition with 2‐O‐Benzylglyceraldehyde

Wehner

Jäger

1990

Angew. Chem. Int. Ed. Engl.

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P-02-C1 angle is less acute than in epo~ides.[~l The most interesting feature of this structure is that it keeps the "memory" of its phosphaalkene precursor. The sum of the W-P-C6, W-P-C1, and Cl-P-C6 angles (357.3') is close to 360°, as in the parent phosphaalkene complex.r3b1 The plane of the oxaphosphirane ring is almost orthogonal to the WPCl C6 mean plane [90.3(0.2)"]. The phosphorus atom appears to retain its initial sp2 hybridization. Even the P-C1 bond [1.778(6) A] is shorter than expected for a normal P-C single bond. The structure of 3 also shows that the epoxidation of the P = C double bond takes place with retention of the initial trans stereochemistry of 1 [C3-P-CI-C6 dihedral angle 161.3(5)"]. However, with the less hindered phosphaalkene complex 2, this retention is not complete. Indeed, the epoxidation of 2 mainly leads to 4.[*] The 'H-NMR spectrum of 4, like that of 3 shows no H-C1-P coupling.r41 Thus, 4 probably has the same trans stereochemistry as 3. However, besides 4 (h31P = +2.9 in C,D,), another compound 5 (h31P = +6.2) is produced in minor amounts (ca. 10%). This compound is probably the cis isomer corresponding to 4. Finally, the main decomposition path of the oxaphosphiranes 3 and 4 in the mass spectrometer involves splitting of the ring into the terminal phosphinidene complex [Mes-P=W(CO),] and the aldehydes RCHO. This process is exactly the reverse of the first described synthesis of this ring."] ExperimentalA solution of m-chloroperbenzoic acid (1.9 g, 1.1 x lo-, mol) in THF (10 mL) was added dropwise to a solution of the phosphaalkene complex 1 (5.3 g, 1 x lo-, mol) in THF (30 mL). The reaction was slightly exothermic. After evaporation of T H E the residue was extracted with hexane. The extract after removal of hexane was recrystallized from pentane/CH,CN. 5.0 g of 3 (-86%). colorless crystals: m.p. 68-69 "C. The same procedure with 2 gave 4 in 40% yield after recrystallization; m.p. 61 -64°C (along with ca 10% of the cis isomer).

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Nucleoside, V. 6‐Dimethylamino‐purin‐Nucleoside der 3‐Amino‐3‐desoxy‐β‐D‐glucose, ‐mannose und ‐galaktose

Abstract: Perjodat-Oxydation von 6-Dimethylamino-9-[P-~-ribofuranosyl]-purin (4) und anschlieRende Nitromethan-Cyclisierung liefert ein Gemisch von 3'-Nitro-hexosyl-dimethylaminopurinen (75 %), das durch fraktionierte Kristallisation in die gluco-, manno-und galakto-Isomeren

Cited by 9 publications

References 20 publications

Synthesis of iminopolyols via Henry reaction: a short route to the α-manno- sidase inhibitor 1,4-dideoxy-1,4-imino-D-mannitol and to amino analogues†,1

Synthesis of iminopolyols via Henry reaction: a short route to the α-manno- sidase inhibitor 1,4-dideoxy-1,4-imino-D-mannitol and to amino analogues†,1

Synthese von D‐ und L‐2‐Amino‐2‐desoxyarabinose sowie von D‐ und L‐1,4‐Didesoxy‐1,4‐iminolyxit durch (C₂ + C₃)‐Nitroaldol‐Addition mit 2‐O‐Benzylglycerinaldehyd

Synthesis of D‐ and L‐2‐Amino‐2‐deoxyarabinose and 1,4‐Dideoxy‐1,4‐iminolyxitol by (C₂ + C₃)‐Nitroaldol Addition with 2‐O‐Benzylglyceraldehyde

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Nucleoside, V. 6‐Dimethylamino‐purin‐Nucleoside der 3‐Amino‐3‐desoxy‐β‐D‐glucose, ‐mannose und ‐galaktose

Abstract: Perjodat-Oxydation von 6-Dimethylamino-9-[P-~-ribofuranosyl]-purin (4) und anschlieRende Nitromethan-Cyclisierung liefert ein Gemisch von 3'-Nitro-hexosyl-dimethylaminopurinen (75 %), das durch fraktionierte Kristallisation in die gluco-, manno-und galakto-Isomeren

Cited by 9 publications

References 20 publications

Synthesis of iminopolyols via Henry reaction: a short route to the α-manno- sidase inhibitor 1,4-dideoxy-1,4-imino-D-mannitol and to amino analogues†,1

Synthesis of iminopolyols via Henry reaction: a short route to the α-manno- sidase inhibitor 1,4-dideoxy-1,4-imino-D-mannitol and to amino analogues†,1

Synthese von D‐ und L‐2‐Amino‐2‐desoxyarabinose sowie von D‐ und L‐1,4‐Didesoxy‐1,4‐iminolyxit durch (C2 + C3)‐Nitroaldol‐Addition mit 2‐O‐Benzylglycerinaldehyd

Synthesis of D‐ and L‐2‐Amino‐2‐deoxyarabinose and 1,4‐Dideoxy‐1,4‐iminolyxitol by (C2 + C3)‐Nitroaldol Addition with 2‐O‐Benzylglyceraldehyde

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Product

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Synthese von D‐ und L‐2‐Amino‐2‐desoxyarabinose sowie von D‐ und L‐1,4‐Didesoxy‐1,4‐iminolyxit durch (C₂ + C₃)‐Nitroaldol‐Addition mit 2‐O‐Benzylglycerinaldehyd

Synthesis of D‐ and L‐2‐Amino‐2‐deoxyarabinose and 1,4‐Dideoxy‐1,4‐iminolyxitol by (C₂ + C₃)‐Nitroaldol Addition with 2‐O‐Benzylglyceraldehyde