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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 21, 1991 - Issue 2
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Original Articles

Preparation and Storage of (R)-2,3-O-Isopropylideneglyceraldehyde (D-Glyceraldehyde Acetonide)

L. W. Hertel Lilly Research Laboratories, Eli Lilly and Company Lilly Corporate Center Indianapolis, Indiana, 46285
,
C. S. Grossman Lilly Research Laboratories, Eli Lilly and Company Lilly Corporate Center Indianapolis, Indiana, 46285
&
J. S. Kroin Lilly Research Laboratories, Eli Lilly and Company Lilly Corporate Center Indianapolis, Indiana, 46285
Pages 151-154 | Received 29 Oct 1990, Published online: 23 Sep 2006

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Jorge L. de O. Domingos, GuilhermeV.M. de A. Vilela, PauloR.R. Costa & Ayres G. Dias. (2004) Crude D‐(+)‐Glyceraldehyde Obtained from D‐Mannitol‐Diacetonide by Oxidative Cleavage with Sodium Periodate: Its Reactions with Nucleophilic Species. Synthetic Communications 34:4, pages 589-598.
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E.E. Nifantyev, A.M. Koroteev, M.P. Koroteev, S.V. Meshkov, V.K. Belsky & A.R. Bekker. (1996) SYNTHESIS AND STRUCTURE OF SOME STABLE PHOSPHOLANE-PHOSPHOLANES. Phosphorus, Sulfur, and Silicon and the Related Elements 113:1-4, pages 1-13.
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P.K. Sharma, S.K. Srivastava & S. Sharma. (1995) A New Synthesis of (4R, 5S)-2,2-Dimethyl-5-[(Z)-2-pentenyl]-1,3-dioxolane-4-carboxaldehyde. Synthetic Communications 25:8, pages 1249-1253.
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Piotr Raubo & Jerzy Wicha. (1993) Enantioselective Silicon-Mediated Synthesis of Glyceraldehyde Derivatives from Propargyl Alcohol. Synthetic Communications 23:9, pages 1273-1288.
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Estefanía Dibello, Margarita Brovetto, Gustavo Seoane & Daniela Gamenara. (2013) Concise synthesis of orthogonally diprotected l-glyceraldehyde. Tetrahedron Letters 54:44, pages 5895-5897.
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Balraj Gopula, Way-Zen Lee & Hsyueh-Liang Wu. (2013) Preparation of Chiral α-Substituted Alaninates through an Efficient Diastereoselective Synthesis of Trisubstituted Allylic Alcohols. Chemistry - An Asian Journal 8:1, pages 80-83.
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Michael Fischer, Christoph Schmölzer, Christina Nowikow & Walther Schmid. (2011) Indium-Mediated Allenylation of Aldehydes and Its Application in Carbohydrate Chemistry: Efficient Synthesis of D-Ribulose and 1-Deoxy-D-ribulose. European Journal of Organic Chemistry 2011:9, pages 1645-1651.
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Abdullah M. Al Majid. (2010) Synthesis of some novel sulfonyl ester derivatives derived from d-mannitol. Journal of Saudi Chemical Society 14:3, pages 257-260.
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Christopher R. Schmid & Jerry D. Bryant. 2003. Organic Syntheses. Organic Syntheses 6 6 .
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Jing-Song You, Ming-Yuan Shao & Han-Mou Gau. (2000) Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by Titanium(IV) Complexes of Diol Derivatives of d -Mannitol and the Spectroscopic Study of the Catalytic System . Organometallics 19:17, pages 3368-3373.
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Raül Fernández, M. Isabel Matheu, Raouf Echarri & Sergio Castillón. (1998) Synthesis of 2-deoxy-3,5-di-O-benzoyl-2,2-difluoro-D-ribose from D-glucose and D-mannose. A formal synthesis of gemcitabine. Tetrahedron 54:14, pages 3523-3532.
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Zoltán Györgydeák & István F. Pelyvás. 1998. Monosaccharide Sugars. Monosaccharide Sugars 375 469 .
William R. Roush, Melissa L. Reilly, Kazuo Koyama & Bradley B. Brown. (1997) A Formal Total Synthesis of (+)-Tetronolide, the Aglycon of the Tetrocarcins:  Enantio- and Diastereoselective Syntheses of the Octahydronaphthalene (Bottom-Half) and Spirotetronate (Top-Half) Fragments. The Journal of Organic Chemistry 62:25, pages 8708-8721.
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Ravi P. Nargund, Meng-Hsin Chen, David B.R. Johnston, Khaled J. Barakat, James R. Tata, Kang Cheng, Thomas M. Jacks, Wanda W.-S. Chan, Liente Wei, Bridget R. Butler, Gerard J. Hickey, Roy G. Smith & Arthur A. Patchett. (1996) Peptidomimetic growth hormone secretagogues: synthesis and biological activities of analogs varied at the indole nucleus of the prototypical spiropiperidine L-162,752. Bioorganic & Medicinal Chemistry Letters 6:14, pages 1731-1736.
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Chuansheng Niu, Teresia Pettersson & Marvin J. Miller. (1996) Enantioselective Total Syntheses of [6 R ,7 R ] and [6 S ,7 S ] Tricyclic β-Lactams . The Journal of Organic Chemistry 61:3, pages 1014-1022.
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Jens Nieschalk, Andrei S Batsanov, David O'Hagan & Judith Howard. (1996) Synthesis of monofluoro- and difluoro- methylenephosphonate analogues of sn-glycerol-3-phosphate as substrates for glycerol-3-phosphate dehydrogenase and the X-ray structure of the fluoromethylenephosphonate moiety. Tetrahedron 52:1, pages 165-176.
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Laurent Dubois, Gilbert Dorey, Pierre Potier & Robert H Dodd. (1995) Preparation of the (R) and (S) enantiomers of 10-hydroxymethylfuro[3,4-c]-β-carboline-2(10H)one, the first example of a benzodiazepine receptor ligand of the β-carboline family having a stereogenic center. Tetrahedron: Asymmetry 6:2, pages 455-462.
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Robert J. DeVita, William R. Schoen, Michael H. Fisher, Alison J. Frontier, Judith M. Pisano, Matthew J. WyvrattJr.Jr., Kang Cheng, Wanda W.-S. Chan, Bridget S. Butler, Gerard J. Hickey, Thomas M. Jacks & Roy G. Smith. (1994) Benzolactam growth hormone secretagogues: Carboxamides as replacements for the 2′-tetrazole moiety of L-692,429. Bioorganic & Medicinal Chemistry Letters 4:18, pages 2249-2254.
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Yung‐Son Hon, Pei‐Pei Sun, Hui‐Ling Lu & Nein‐Chen Chang. (2013) Comparison of Stereoselectivity of Intramolecular Cyclization of Aldehydes Tethered with Conjugated Esters Induced by O ‐Stannyl and O ‐Samarium Ketyls to Form the Tetrahydrofuran Ring Systems . Journal of the Chinese Chemical Society 41:4, pages 445-458.
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Wei Zou & Walter A. Szarek. (1994) An efficient conversion of d-mannitol into d-fructose and 1,5-dideoxy-1,5-imino-d-mannitol (1-deoxymannojirimycin). Carbohydrate Research 254, pages 25-33.
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Wolfgang H. Binder, Reinhard H. Prenner & Walther Schmid. (1994) Indium-mediated allylation of aldehydes: A convenient route to 2-deoxy and 2,6-dideoxy carbohydrates. Tetrahedron 50:3, pages 749-758.
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Peter Metz & Andreas Schoop. (1993) Diastereoselective addition of lower order vinylcuprates to (R)-2,3-O-Isopropylideneglyceraldehyde. Tetrahedron 49:46, pages 10597-10608.
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Jeffrey Aubé, Craig J. Mossman & Susan Dickey. (1992) (2S, 3S, 5S)- and (2S, 3S, 5R)-5-carboxaldehyde-2,3-diphenyl-1,4-dioxane as surrogates for optically pure 2,3-O-isopropylideneglyceraldehyde in asymmetric synthesis. Tetrahedron 48:45, pages 9819-9826.
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L. W. HERTEL, C. S. GROSSMAN & J. S. KROIN. (2010) ChemInform Abstract: Preparation and Storage of (R)‐2,3‐O‐Isopropylideneglyceraldehyde (D‐ Glyceraldehyde Acetonide).. ChemInform 22:48.
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