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Volumn 34, Issue 4, 2004, Pages 589-598

Crude D-(+)-Glyceraldehyde Obtained from D-Mannitol-Diacetonide by Oxidative Cleavage with Sodium Periodate: Its Reactions with Nucleophilic Species

Author keywords

D (+) Glyceraldehyde; D (+) Mannitol diacetonide; Nucleophilic additions; Oxidative cleavage

Indexed keywords

AMINE; GLYCERALDEHYDE; MANNITOL; MANNITOL DIACETONIDE; NITRONATE; NITRONE DERIVATIVE; OLIGOMER; ORGANOMETALLIC COMPOUND; PERIODATE SODIUM; PHOSPHONIC ACID DERIVATIVE; PHOSPHORANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 1542426204     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120027706     Document Type: Article
Times cited : (7)

References (21)
  • 1
    • 0001025429 scopus 로고
    • Studies on acetone-glyceraldehyde. IV. Preparation of D-(+)-acetone glycerol
    • (a) Baer, E.; Fischer, H.O.L. Studies on acetone-glyceraldehyde. IV. Preparation of D-(+)-acetone glycerol. J. Biol. Chem. 1939, 128 (2), 463-473;
    • (1939) J. Biol. Chem. , vol.128 , Issue.2 , pp. 463-473
    • Baer, E.1    Fischer, H.O.L.2
  • 2
    • 0000150874 scopus 로고
    • An improved preparation of (+)-2,3-O-isopropylidene-D-glyceraldehyde
    • (b) Jackson, D.Y. An improved preparation of (+)-2,3-O-isopropylidene-D-glyceraldehyde. Synth. Comm. 1988, 18 (4), 337-341;
    • (1988) Synth. Comm. , vol.18 , Issue.4 , pp. 337-341
    • Jackson, D.Y.1
  • 3
    • 33751498908 scopus 로고
    • Synthesis of 2,3-O-isopropylidene-D-glyceraldehyde in high chemical and optical purity-Observations on the development of a practical bulk process
    • (c) Schmid, C.R.; Bryant, J.D.; Dowlatzedah, M.; Phillips, J.L.; Prather, D.E.; Schantz, R.D.; Sear, N.L.; Vianco, C.S. Synthesis of 2,3-O-isopropylidene-D-glyceraldehyde in high chemical and optical purity-Observations on the development of a practical bulk process. J. Org. Chem. 1991, 56 (12), 4056-4058;
    • (1991) J. Org. Chem. , vol.56 , Issue.12 , pp. 4056-4058
    • Schmid, C.R.1    Bryant, J.D.2    Dowlatzedah, M.3    Phillips, J.L.4    Prather, D.E.5    Schantz, R.D.6    Sear, N.L.7    Vianco, C.S.8
  • 4
    • 0002591784 scopus 로고
    • D-(R)-glyceraldehyde acetonide
    • (d) Schmid, C.R.; Bryant, J.D. D-(R)-glyceraldehyde acetonide. Org. Synth. 1995, 72, 6-13;
    • (1995) Org. Synth. , vol.72 , pp. 6-13
    • Schmid, C.R.1    Bryant, J.D.2
  • 5
    • 0025828998 scopus 로고
    • Preparation and storage of (R)-2,3-O-isopropylideneglyceraldehyde (D-glyceraldehyde acetonide)
    • (e) Hertel, L.W.; Grossman, C.S.; Kroin, J.S. Preparation and storage of (R)-2,3-O-isopropylideneglyceraldehyde (D-glyceraldehyde acetonide). Synth. Comm. 1991, 21 (2), 151-154;
    • (1991) Synth. Comm. , vol.21 , Issue.2 , pp. 151-154
    • Hertel, L.W.1    Grossman, C.S.2    Kroin, J.S.3
  • 6
    • 34250667360 scopus 로고
    • (R)-2,3-O-isopropylideneglyceraldehyde and (S)-2,3-O-isopropylideneglyceraldehyde in stereoselective organic synthesis
    • (f) Jurczak, J.; Pikul, S.; Bauer, T. (R)-2,3-O-isopropylideneglyceraldehyde and (S)-2,3-O-isopropylideneglyceraldehyde in stereoselective organic synthesis. Tetrahedron 1986, 42 (2), 447-488.
    • (1986) Tetrahedron , vol.42 , Issue.2 , pp. 447-488
    • Jurczak, J.1    Pikul, S.2    Bauer, T.3
  • 7
    • 84988055616 scopus 로고
    • Convenient one-pot conversion of alcohols into esters via hemiacetal intermediates
    • Lichtenthaler, F.W.; Jarglis, P.; Lorenz, K. Convenient one-pot conversion of alcohols into esters via hemiacetal intermediates. Synthesis 1988, (10), 790-792.
    • (1988) Synthesis , Issue.10 , pp. 790-792
    • Lichtenthaler, F.W.1    Jarglis, P.2    Lorenz, K.3
  • 8
    • 0029987021 scopus 로고    scopus 로고
    • Straightforward synthesis of L-isoserinal
    • Junquera, F.; Merchan, F.L.; Merino, P.; Tejero, T. Straightforward synthesis of L-isoserinal. Tetrahedron 1996, 52 (20), 7045-7052.
    • (1996) Tetrahedron , vol.52 , Issue.20 , pp. 7045-7052
    • Junquera, F.1    Merchan, F.L.2    Merino, P.3    Tejero, T.4
  • 9
    • 0030691081 scopus 로고    scopus 로고
    • Diasteroselective nucleophilic addition of acetylide to N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN). Stereodivergent synthesis of β-hydroxy-α-(hydroxyamino)-and β-hydroxy-α -amino acids
    • Merino, P.; France, S.; Merchan, F.L.; Tejero, T. Diasteroselective nucleophilic addition of acetylide to N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN). Stereodivergent synthesis of β-hydroxy-α-(hydroxyamino)-and β-hydroxy-α -amino acids. Tetrahedron-Asymmetry 1997, 8 (20), 3489-3496.
    • (1997) Tetrahedron-Asymmetry , vol.8 , Issue.20 , pp. 3489-3496
    • Merino, P.1    France, S.2    Merchan, F.L.3    Tejero, T.4
  • 10
    • 0029996372 scopus 로고    scopus 로고
    • Enantioselective synthesis of 1,2-acetonide of (2S,3R)-3-N-boc-3-amino-4-phenyl-1,2-butanediol
    • Remuzon, P.; Dussy, C.; Jacquet, J.P.; Roty, P.; Bouzard, D. Enantioselective synthesis of 1,2-acetonide of (2S,3R)-3-N-boc-3-amino-4-phenyl-1,2-butanediol. Tetrahedron-Asymmetry 1996, 7 (4), 1181-1188.
    • (1996) Tetrahedron-Asymmetry , vol.7 , Issue.4 , pp. 1181-1188
    • Remuzon, P.1    Dussy, C.2    Jacquet, J.P.3    Roty, P.4    Bouzard, D.5
  • 11
    • 0021056504 scopus 로고
    • β-1-selective adrenoceptor antagonists. 1. Synthesis and beta-adrenergic blocking activity of a series of binary (aryloxy)propanolamines
    • Kierstead, R.W.; Faraone, A.; Mennona, F.; Mullin, J.; Guthrie, R.W.; Crowley, H.; Simko, B.; Blaber, L.C. β-1-selective adrenoceptor antagonists. 1. Synthesis and beta-adrenergic blocking activity of a series of binary (aryloxy)propanolamines. J. Med. Chem. 1983, 26 (11), 1561-1569.
    • (1983) J. Med. Chem. , vol.26 , Issue.11 , pp. 1561-1569
    • Kierstead, R.W.1    Faraone, A.2    Mennona, F.3    Mullin, J.4    Guthrie, R.W.5    Crowley, H.6    Simko, B.7    Blaber, L.C.8
  • 12
    • 0000437889 scopus 로고
    • A practical synthesis of (S)-5-hydroxymethylfuran-2(5H)-one from 1,2-5,6-di-O-isopropylidene-D-mannose
    • Mann, J.; Partlett, N.K.; Thomas, A. A practical synthesis of (S)-5-hydroxymethylfuran-2(5H)-one from 1,2-5,6-di-O-isopropylidene-D-mannose. J. Chem. Res. 1987, (11), 369.
    • (1987) J. Chem. Res. , Issue.11 , pp. 369
    • Mann, J.1    Partlett, N.K.2    Thomas, A.3
  • 13
    • 0037140816 scopus 로고    scopus 로고
    • A general procedure for a one-pot oxidative cleavage/Wittig reaction of glycols
    • (a) Dunlap, N.K.; Mergo, W.; Jones, J.M.; Carrick, J.D. A general procedure for a one-pot oxidative cleavage/Wittig reaction of glycols. Tetrahedron Lett. 2002, 43 (21), 3923-3925;
    • (2002) Tetrahedron Lett. , vol.43 , Issue.21 , pp. 3923-3925
    • Dunlap, N.K.1    Mergo, W.2    Jones, J.M.3    Carrick, J.D.4
  • 14
    • 0037179167 scopus 로고    scopus 로고
    • In situ oxidative diol cleavage-Wittig processes
    • (b) Outram, H.S.; Raw, S.A.; Taylor, R.J.K. In situ oxidative diol cleavage-Wittig processes. Tetrahedron Lett. 2002, 43 (35), 6185-6187.
    • (2002) Tetrahedron Lett. , vol.43 , Issue.35 , pp. 6185-6187
    • Outram, H.S.1    Raw, S.A.2    Taylor, R.J.K.3
  • 15
    • 33845378126 scopus 로고
    • A nitrile oxide based entry to 2,3-dihydropyran-4-ones-Synthesis of a protected version of compactin lactone in racemic and optically-active forms
    • Kozikowski, A.P.; Li, C.S. A nitrile oxide based entry to 2,3-dihydropyran-4-ones-Synthesis of a protected version of compactin lactone in racemic and optically-active forms. J. Org. Chem. 1985, 50 (6), 778-785.
    • (1985) J. Org. Chem. , vol.50 , Issue.6 , pp. 778-785
    • Kozikowski, A.P.1    Li, C.S.2
  • 16
    • 0028998327 scopus 로고
    • Silica gel-catalyzed addition of methyl nitroacetate to 1,2-3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose and 2,3-O-isopropylidene-D-glyceraldehyde-crystal-structure of methyl 7-acetamido-7-deoxy-1,2-3,4-di-O-isopropylidene-L-threo-α -D-galacto-octopyranuronate
    • Borrachero, P.; Dianez, M.J.; Estrada, M.D.; Gómez-Guillén, M.; Gómez-Sánchez, A.; López-Castro, A.; Pérez-Garrido, S. Silica gel-catalyzed addition of methyl nitroacetate to 1,2-3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose and 2,3-O-isopropylidene-D-glyceraldehyde-crystal-structure of methyl 7-acetamido-7-deoxy-1,2-3,4-di-O-isopropylidene-L-threo-α -D-galacto-octopyranuronate. Carbohydrate Res. 1995, 271 (1), 79-99.
    • (1995) Carbohydrate Res. , vol.271 , Issue.1 , pp. 79-99
    • Borrachero, P.1    Dianez, M.J.2    Estrada, M.D.3    Gómez-Guillén, M.4    Gómez-Sánchez, A.5    López-Castro, A.6    Pérez-Garrido, S.7
  • 17
    • 0032575902 scopus 로고    scopus 로고
    • Synthesis and absolute configuration of the insecticidal sesquilignan (+)-haedoxan A
    • Ishibashi, F.; Taniguchi, E. Synthesis and absolute configuration of the insecticidal sesquilignan (+)-haedoxan A. Phytochemistry 1998, 49 (2), 613-622.
    • (1998) Phytochemistry , vol.49 , Issue.2 , pp. 613-622
    • Ishibashi, F.1    Taniguchi, E.2
  • 18
    • 0001354758 scopus 로고
    • On the steric course of the addition of some organometallic reagents to (R)-2,3-isopropylidene glyceraldehyde - Synthesis of optically-active α-benzyloxy aldehydes, alcohols, carboxylic-acids and 1,2-diols
    • Mulzer, J.; Angermann, A. On the steric course of the addition of some organometallic reagents to (R)-2,3-isopropylidene glyceraldehyde - Synthesis of optically-active α-benzyloxy aldehydes, alcohols, carboxylic-acids and 1,2-diols. Tetrahedron Lett. 1983, 24 (28), 2843-2846.
    • (1983) Tetrahedron Lett. , vol.24 , Issue.28 , pp. 2843-2846
    • Mulzer, J.1    Angermann, A.2
  • 19
    • 0343695074 scopus 로고    scopus 로고
    • Effect of a phosphazene base on the diastereoselectivity of addition of α-sulfonyl carbanions to butyraldehyde and isopropylidene glyceraldehyde
    • Solladié-Cavallo, A.; Roche, D.; Fischer, J.; Decian, A. Effect of a phosphazene base on the diastereoselectivity of addition of α-sulfonyl carbanions to butyraldehyde and isopropylidene glyceraldehyde. J. Org. Chem. 1996, 61 (8), 2690-2694.
    • (1996) J. Org. Chem. , vol.61 , Issue.8 , pp. 2690-2694
    • Solladié-Cavallo, A.1    Roche, D.2    Fischer, J.3    Decian, A.4
  • 20
    • 33947303222 scopus 로고
    • O and S methylation of ambident P-toluenesulfinate anion
    • Meek, J.S.; Fowler, J.S. O and S methylation of ambident P-toluenesulfinate anion. J. Org. Chem. 1968, 33 (9), 3422-3424.
    • (1968) J. Org. Chem. , vol.33 , Issue.9 , pp. 3422-3424
    • Meek, J.S.1    Fowler, J.S.2
  • 21
    • 84980173028 scopus 로고
    • Synthesen in der carotinoid-reihe. 10. Mitteilung - Anwendung der Wittig-reaktion zur synthese von estern des bixins und crocetins
    • Isler, O.; Gutmann, H.; Montavon, M.; Ruegg, R.; Ryser, G.; Zeller, P. Synthesen in der carotinoid-reihe. 10. Mitteilung - Anwendung der Wittig-reaktion zur synthese von estern des bixins und crocetins. Helv. Chim. Acta 1957, 40 (5), 1242.
    • (1957) Helv. Chim. Acta , vol.40 , Issue.5 , pp. 1242
    • Isler, O.1    Gutmann, H.2    Montavon, M.3    Ruegg, R.4    Ryser, G.5    Zeller, P.6


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