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[ CAS No. 18549-40-1 ] {[proInfo.proName]}

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Chemical Structure| 18549-40-1
Chemical Structure| 18549-40-1
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Product Details of [ 18549-40-1 ]

CAS No. :18549-40-1 MDL No. :MFCD00063244
Formula : C9H16O6 Boiling Point : -
Linear Structure Formula :- InChI Key :BGGCXQKYCBBHAH-OZRXBMAMSA-N
M.W : 220.22 Pubchem ID :87704
Synonyms :

Calculated chemistry of [ 18549-40-1 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 6.0
Num. H-bond donors : 3.0
Molar Refractivity : 47.93
TPSA : 88.38 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.45
Log Po/w (XLOGP3) : -0.28
Log Po/w (WLOGP) : -1.42
Log Po/w (MLOGP) : -1.34
Log Po/w (SILICOS-IT) : -0.69
Consensus Log Po/w : -0.46

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.9
Solubility : 27.9 mg/ml ; 0.127 mol/l
Class : Very soluble
Log S (Ali) : -1.12
Solubility : 16.8 mg/ml ; 0.0764 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.94
Solubility : 1920.0 mg/ml ; 8.71 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.33

Safety of [ 18549-40-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 18549-40-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 18549-40-1 ]

[ 18549-40-1 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 76-83-5 ]
  • [ 18549-40-1 ]
  • [ 33737-08-5 ]
YieldReaction ConditionsOperation in experiment
61% With pyridine; at 20℃; for 48h; 1,2-O-Isopropylidene-a-D-glucofuranoside (14) (6.40 g,29 mmol) was dissolved in pyridine (60 mL) and triphyenlmethylchloride(10.44 g, 37.5 mmol) was added.The resulting solution was allowed to stand at rt. withoccasional stirring for 48 h. Then, water was added untilpermanent turbidity has been observed. After 2 h, themixture was poured into ice-water (1000 mL). The whiteprecipitate was filtered, washed with water three times, anddissolved in CHCl3. The solution was washed with 3 % aq.acetic acid until the pH of the aqueous phase becameacidic, after that the organic phase was washed with wateruntil neutrality, and dried (Na2SO4). After evaporation ofthe solvent, the crude product was crystallized from diethylether to provide compound 15 (7.88 g, 61 %); m.p. 137-139 C; a22D = -19.9 (c = 2, CH3OH); 1H NMR(300 MHz, CDCl3), d (ppm): 7.46 (d, J = 8.1 Hz, 6H,ArH), 7.36-7.20 (m, 9H, ArH), 5.95 (d, J = 3.3 Hz, 1H,H-1), 4.51 (d, J = 3.3 Hz, 1H, H-2), 4.34-4.27 (m, 1H,H-3), 4.25-4.16 (m, 1H, H-5), 4.15-4.08 (m, 1H, H-4),3.47-3.41 (m, 1H, H-6a), 3.38-3.29 (m, 2H, H-6b, OH),2.73 (br s, 1H, OH), 1.47 (s, 3H, CCH3), 1.31 (s, 3H,CCH3); 13C NMR (75 MHz, CDCl3), d (ppm): 144.02,128.86, 127.91, 127.35, 111.86, 105.24, 86.46, 82.11,81.74, 78.76, 69.45, 64.62, 26.83, 26.25; HRMS calcd forC28H30O6 462.2042, found 462.2048.
  • 2
  • [ 98-88-4 ]
  • [ 18549-40-1 ]
  • [ 3254-32-8 ]
YieldReaction ConditionsOperation in experiment
75% With pyridine; In dichloromethane; at 20℃; for 4.16667h; To a stirred solution of 2 (1.00 g, 4.54 mmol) in a 1:1 mixture CH2Cl2/Py (10 mL) was added BzCl (0.54 mL, 4.54 mmol) during 10 min. The mixture was stirred at room temperature for 4 h and then evaporated. The residue was purified by flash column chromatography (1:1 EtOAc/toluene) to afford pure 3 (1.10 g, 75%) as a colourless solid.
72% To a mixture of Bu2SnO (7.92 g, 31.8 mmol) and triol compound 6 (7.0 g, 31.8 mmol) dry methanol (210 mL) was added. The mixture was heated at reflux for 10 h. The solvent was evaporated and residue was dried under vacuum. The crude product was dissolved in 1,4-dioxane (210 mL), after which were added benzoyl chloride (4.92 g, 35.0 mmol) and DMAP (0.1 mol equiv). The mixture was left for 12-16 h and the reaction was monitored by TLC. The mixture was concentrated in vacuo at 40 C. The tin compounds were removed on silica gel column chromatography by eluting with CHCl3, and a pure compound was obtained by ethyl acetate elute to give mono 6-O-benzoylated 7 7.4 g (22.9 mmol, 72%). [alpha]D20 = +7.1 (c 1.05, CHCl3); IR (KBr): 3485, 2952, 2795, 1690, 1275, 1235, 1075, 1029 cm-1. 1H NMR (300 MHz, CDCl3): delta 1.32 (s,3H), 1.48 (s, 3H), 3.11 (d, J = 3.8 Hz, 1H), 3.20 (d, J = 3.2 Hz, 1H), 4.19 (dd, J = 3.0, 6.8 Hz, 1H), 4.33-4.40 (m, 1H), 4.41-4.43 (m, 1H), 4.50 (dd, J = 6.04, 11.3 Hz, 1H), 4.56 (d, J = 3.78, 1H), 5.99 (d, J -3.8, 1H), 7.45 (t, J = 7.4, 2H), 7.57 (t, J = 7.4 Hz, 1H), 8.05 (d, J = 7.1 Hz, 2H). 13C NMR (75 MHz, CDCl3): delta 24.9, 25.5, 66.0, 66.5, 73.3, 79.3, 84.5, 104.5, 111.0, 127.6, 128.8, 132.4, 132.8, 166.4. HRMS (ESI-MS): m/z [M+H]+ calcd for C16H21O7: 325.1287; found: 325.1281.
  • 3
  • [ 582-52-5 ]
  • [ 18549-40-1 ]
YieldReaction ConditionsOperation in experiment
93% With solid catalyst supported on silica gel, sulfuric acid, acetic acid; In dichloromethane; at 30℃; for 14h; 1) weigh the 0.1 mol of diacetone glucose and 3mol ofdichloromethane and stirred until it mixed evenly; 2) into the above mentioned reaction system added 0.01mol ofSilica-Supported Sulfuric Acid-glacial acetic acid (with the content count of hydrogen titration) and stirred at 30oC for14h; 3) filtering, washing the filter cake methanol and the combined filtrate and washings, 40 C and concentrated under reduced pressure to a solid, was added a molar ratio of 1: 2: 6 tert-butyl methyl ether and iso-hexane, 3 C crystallization 3h, get monopropyl fork glucose 0. 093mol, 97% purity, 93% yield.
85% With water; acetic acid; at 25℃; d-Glucose diacetonide 5 (10 g 38.4 mmol) was dissolved in a mixture of acetic acid (100 mL) and water (50 mL). The mixture was stirred for 12 h at 25 C. The crude was concentrated under vacuum at 50 C. A pure compound was obtained by recrystallization from ethyl acetate to give triol compound 6 (7.2 g, 32.64 mmol, 85%).[alpha]D20 = -11.2 (c 1.1, H2O); IR (KBr): 3420, 2952, 2795, 1434, 1322, 1275, 1235, 1095, 1043 cm-1. 1H NMR (300 MHz, CD3OD): delta 1.32 (s, 3H), 1.47 (s, 3H), 3.62 (dd, J = 6.0, 11.7 Hz, 1H), 3.79 (dd, J = 3.0, 11.8 Hz, 1H), 3.90-3.94 (m, 1H), 4.04 (dd, J = 2.6, 8.3 Hz, 1H), 4.22 (d, J = 2.3 Hz, 1H), 4.51 (d, J = 3.4 Hz, 1H), 5.90 (d, J = 3.4 Hz, 1H). 13C NMR (75 MHz, CD3OD): delta 26.4, 27.0, 65.3, 70.4, 75.5, 81.3, 86.5, 106.4, 112.7. HRMS (ESI-MS): m/z [M+Na]+ calcd for C9H16O6Na: 243.0845; found: 243.0850.
85% With silica supported polyphosphoric acid; In acetonitrile; at 55℃; for 0.5h; General procedure: 3-O-Benzyl-1,2:5,6-di-O-isopropylidene-a-D-allofuranose (1) (100 mg) wasdissolved in CH3CN (2 ml) and PPA-SiO2 (100mg, 0.16 mmol, based uponPPA weight) was added.[3] The reaction mixture was stirred at 55 C for30 min. After completion of the reaction (monitored by TLC), the mixturewas allowed to cool to room temperature. Further, the reaction mixturewas filtered through filter paper, washed with CH3CN (1 x 5 ml).Evaporation of the solvent under reduced pressure yielded 3-O-Benzyl-1,2-O-isopropylidene-a-D-allofuranose (2)[17] as a crude oily compound. Thecrude compound 2 was purified by column chromatography to obtain colorless oily compound (75 mg, 85%); Rf0.31 (petroleum ether: EtOAc 1:1).
78% With water; iodine; In acetonitrile; at 20℃; for 7h; 1,2-O-isopropylidene-alpha-D-glucofuranosewas prepared by a modification of the method of Yadav et al.[32] Iodine (1.47 g, 5.8 mmol, 0.3eq.) was added to a solution of 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose (5.00 g, 19.2mmol) in MeCN (270 mL). H2O (2 mL) was added, and the reaction mixture was stirred atroom temperature for 7 h. The reaction was quenched with saturated aqueous Na2S2O3 solutionand extracted into EtOAc (5 x 200 mL). The organic layers were dried over anhydrousNa2SO4, the solvent removed and the crude mixture was purified by column chromatography(silica) using EtOAc/hexane 2:1, EtOAc and EtOAc/MeOH 1:0.01 to give the product as awhite powder (3.29 g, 14.9 mmol, 78% yield). Rf 0.23 (EtOAc, silica); [alpha]26D -18.3 (c 1.00, H2O)(lit. [alpha]22D -12.0 (c 1.0, H2O)[33]).

Reference: [1]Carbohydrate Research,1995,vol. 274,p. 263 - 268
[2]Journal of Organic Chemistry,2007,vol. 72,p. 9782 - 9785
[3]European Journal of Organic Chemistry,2013,p. 7941 - 7951
[4]Journal of Organic Chemistry,2020
[5]Carbohydrate Research,1985,vol. 137,p. 259 - 264
[6]Carbohydrate Research,2008,vol. 343,p. 1801 - 1807
[7]RSC Advances,2016,vol. 6,p. 63445 - 63462
[8]Synlett,2000,p. 110 - 112
[9]Tetrahedron,2004,vol. 60,p. 11465 - 11475
[10]Carbohydrate Research,2005,vol. 340,p. 1661 - 1667
[11]Russian Journal of Organic Chemistry,2014,vol. 50,p. 670 - 677
    Zh. Org. Khim.,2014,vol. 50,p. 684 - 690,7
[12]Tetrahedron,1989,vol. 45,p. 327 - 336
[13]Tetrahedron,2002,vol. 58,p. 253 - 259
[14]Patent: CN104031099,2016,B .Location in patent: Paragraph 0034-0037
[15]Synthetic Communications,2003,vol. 33,p. 1185 - 1193
[16]Tetrahedron Letters,2005,vol. 46,p. 8745 - 8748
[17]Tetrahedron Letters,2007,vol. 48,p. 9073 - 9076
[18]Synthesis,2005,p. 708 - 710
[19]Tetrahedron Letters,2012,vol. 53,p. 1287 - 1291
[20]Chemistry Letters,2001,p. 430 - 431
[21]Tetrahedron Letters,2006,vol. 47,p. 6987 - 6991
[22]Journal of Carbohydrate Chemistry,2013,vol. 32,p. 184 - 192
[23]Tetrahedron Asymmetry,2016,vol. 27,p. 788 - 790
[24]Journal of Carbohydrate Chemistry,2020,vol. 39,p. 63 - 74
[25]Carbohydrate Research,1994,vol. 258,p. 59 - 76
[26]Tetrahedron Letters,1986,vol. 27,p. 3827 - 3830
[27]Synthetic Communications,1999,vol. 29,p. 2807 - 2815
[28]PLoS ONE,2019,vol. 14
[29]Synthetic Communications,2000,vol. 30,p. 2019 - 2028
[30]European Journal of Medicinal Chemistry,1989,vol. 24,p. 471 - 474
[31]Synlett,2011,p. 821 - 825
[32]Journal of the American Chemical Society,1929,vol. 51,p. 519,522
[33]Journal of the Chemical Society,1945,p. 119,121
[34]Helvetica Chimica Acta,1946,vol. 29,p. 139,144
[35]Zhurnal Obshchei Khimii,1957,vol. 27,p. 2972,2973; engl. Ausg. S. 2877
[36]Chemische Berichte,1928,vol. 61,p. 1735,1738
[37]Acta Chemica Scandinavica (1947),1954,vol. 8,p. 866
[38]Tetrahedron,1994,vol. 50,p. 10167 - 10182
[39]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 3978 - 3986
[40]Heterocycles,2000,vol. 52,p. 519 - 523
[41]Journal of labelled compounds and radiopharmaceuticals,2005,vol. 48,p. 845 - 854
[42]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2597 - 2621
[43]Tetrahedron Asymmetry,2006,vol. 17,p. 819 - 821
[44]Organic and Biomolecular Chemistry,2006,vol. 4,p. 551 - 557
[45]Analytical Chemistry,2006,vol. 78,p. 8406 - 8411
[46]Tetrahedron Letters,2008,vol. 49,p. 1961 - 1964
[47]Journal of Organic Chemistry,2009,vol. 74,p. 3179 - 3182
[48]Chemistry - A European Journal,2016,vol. 22,p. 12884 - 12890
[49]Journal of Organic Chemistry,2018,vol. 83,p. 185 - 193
  • 6
  • [ 100-39-0 ]
  • [ 18549-40-1 ]
  • [ 53928-30-6 ]
YieldReaction ConditionsOperation in experiment
97% With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃; for 2.5h; To a cooled (0 C) and stirred solution of 2 (1.00 g, 4.54 mmol) in dry DMF (30 mL) were added successively 80% NaH (0.817 g, 34.06 mmol) and BnBr (2.0 mL, 16.82 mmol). The mixture was stirred at 0 C for 0.5 h and then at room temperature for 2 h. Methanol (7 mL) was finally added, and the mixture was stirred at room temperature for the additional 15 min and evaporated. The residue was suspended in water (150 mL), and extracted first with CH2Cl2 (3×20 mL) and finally with EtOAc (30 mL). The combined organic solutions were dried and evaporated. The remaining crude 7 was purified by flash column chromatography (3:1 light petroleum/Et2O) to afford pure 7 (2.166 g, 97%) as a colourless glassy solid
90% With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20℃; for 24.5h;Inert atmosphere; Under N2, 1 (1.00 g,4.5 mmol) was dissolved in anhydrous DMF (24 mL). Sodium hydride in a 60% oily dispersion(0.90 g, 22.5 mmol, 5 eq.) was added portionwise with vigorous stirring. After stirring for 30min, benzyl bromide (2.80 mL, 22.5 mmol, 5 eq.) was added dropwise. The reaction mixturewas stirred at room temperature, under N2 for 24 h and then treated with H2O (150 mL) andneutralised with 1Mhydrochloric acid. The product was extracted into DCM (3 x 150 mL),and the organic layer was dried over Na2SO4 and the solvent removed. The product was purified by column chromatography (silica) with hexane/EtOAc 8:1 eluent to yield 2 as a lightyellow oil (2.01 g, 4.1 mmol, 90% yield).Rf 0.46 (hexane/EtOAc 2:1, silica); [alpha]26D -33.8 (c 2.03, CHCl3) (lit. [alpha]20D -36 (c 1.0, CHCl3)[34]; [alpha]25D -33 (c 9.3, CHCl3)[35]).
  • 7
  • [ 18162-48-6 ]
  • [ 18549-40-1 ]
  • [ 85951-10-6 ]
YieldReaction ConditionsOperation in experiment
90% With 1H-imidazole; In dichloromethane; at 0 - 60℃; will1,2-O-isopropylidene-alpha-D-glucofuranose (2 g, 9.09 mmol)Was dissolved in 20 mL of dichloromethane, and imidazole (0.74 g, 10.91 mmol) and TBSCl (1.64 g, 10.91 mmol) were added,After stirring at 0-60 C for 2-36 hours, the reaction solution was poured into ice water,Extracted with dichloromethane, and the organic layer was collected and washed twice with saturated brine,Dried over anhydrous sodium sulfate, filtered, concentrated,Separation by column (n-hexane / ethyl acetate: 5/1) gave colorless oily substance 2 (2.72 g, 8.14 mmol, 90%).
  • 8
  • [ 18549-40-1 ]
  • [ 19684-32-3 ]
YieldReaction ConditionsOperation in experiment
98% To a 150 mL three-necked flask was added 2.20 g (10.67 mmol) of 1,2-O-isopropylidene-alpha-D-glucofuranose,12.72 g (21.34 mmol) of tributyltin oxide, 1.3 g of 4A molecular sieves and 60 mL of trichloromethane were added and the mixture was stirred under reflux for about 1 h until 1,2-O-isopropylidene-alpha-D- Furan Glucose is completely dissolved. The system will naturally cool to room temperature and then placed in the ice bath conditions, drop by adding liquid bromine and continue to stir until the liquid bromine drops after the reddish brown no longer fade so far, continue to stir for 5min, then the system color is still light reddish brown, You can stop the reaction. The reaction mixture was directly passed through a column chromatography on silica gel, the tin compound was removed with trichloromethane as an eluent, and the target product was eluted with ethyl acetate as an eluent. The eluate containing the desired product And the resulting mixture was dried to obtain 2.13 g of a pale yellow syrupy liquid 1,2-O-isopropylidene-5-oxo-alpha-glucofuran, and the yield was 98%.
  • 10
  • [ 18549-40-1 ]
  • [ 3067-56-9 ]
  • [ 20513-98-8 ]
  • 11
  • [ 18549-40-1 ]
  • [ 72599-27-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) dibutylin oxide hemihydrate, 2.) Br2 / 1.) MeOH, reflux, 1.5 h, 2.) CH2Cl2, 0 deg C, 10 min 2: 70 percent / Dowex 50W-X8 / H2O / 36 h / 25 °C 3: 55 percent / HOAc, NaBH3CN / methanol / 1.) -78 deg C, 2 h, 2.) r.t., 20 h
  • 12
  • (1S,2S)-2-[(3,4-dichlorophenyl)carbonyl]cyclopropane-1-carboxylic acid [ No CAS ]
  • [ 18549-40-1 ]
  • [(5R,6S,6aR)-6-hydroxy-tetrahydro-2H-furo[2,3-d] [1,3] dioxol-5-yl]methyl (1S,2S)-2-[(3,4-dichlorophenyl)carbonyl]cyclopropane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With pyridine; pivaloyl chloride; triethylamine; In tetrahydrofuran; at 20℃; for 19h;Inert atmosphere; Step 1, [(5R,6S,6aR)-6-Hydroxy-tetrahydro-2H-furo [2,3-dj [1 ,3j dioxol-5-ylj methyl (1S,2S)- 2- [(3,4-dichlorophenyl)carbonylj cyclopropane- 1-carboxylate[00203j See, e.g., Smith et al, Journal of Organic Chemistry, 1980, 5000-5002. [00204j Triethylamine (0.08 mL, 0.61 mmol) and 2,2-dimethylpropanoyl chloride (0.07 mL, 0.61 mmol) were added dropwise sequentially to a stirred solution of(1S,2S)-2-[(3,4- dichlorophenyl)carbonyl]cyclopropane-1-carboxylic acid (0.16 g, 0.61 mmol) in THF (5 mL) and the mixture was stirred at room temperature for 1 hour. After this time the mixture wasadded portion wise to a solution of (1 R)- 1- [(3 aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro- 2H-furo[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol (0.4 g, 1.82 mmol) in pyridine (5 mL) and the reaction mixture was stirred at room temperature under a nitrogen atmosphere for 18 hours. The resulting mixture was concentrated and the residue partitioned between DCM (50m1) and water (lOml). The organic layer was separated, dried (MgSO4), filtered and concentrated. The resulting residue was then purified by flash column chromatography (elution: 100% ethyl acetate) to give the title compound (0.3 g, 99% yield) as a white solid. Tr = 2.03 mm m/z (ESj (M+Na) 485.
  • 13
  • [ 18549-40-1 ]
  • [ 18422-58-7 ]
YieldReaction ConditionsOperation in experiment
64% With periodic acid; In acetonitrile; at 20℃; for 20h; Procedure B. A solution of 4 (1.948 g, 8.85 mmol) and H5IO6 (4.032 g, 17.69 mmol) in dry CH3CN (210 mL) was stirred at room temperature for 20h. The mixture was filtered through a Celite pad and evaporated. The residue was purified by flash column chromatography (1:2, 1:1, 2:1 t2/light petroleum) to afford pure 5 (1.226 g, 64%) as a white solid.
  • 14
  • C9H16O7S [ No CAS ]
  • [ 100-58-3 ]
  • [ 945-51-7 ]
  • [ 18549-40-1 ]
YieldReaction ConditionsOperation in experiment
1: 89% 2: 65% In tetrahydrofuran at 0℃; for 1.5h; Inert atmosphere; 3.4. Reaction of (R)-1,2-O-Isopropylidene-3,5-O-Sulfinyl- -d-Glucofuranose (+)-(R)-4 withPhenylmagnesium Bromide A solution of (+)-(R)-4 (0.133 g, 0.5 mmol) in of THF (5 mL) was cooled to 0 C and treated with a solution of freshly prepared phenylmagnesium bromide (1.5 mmol) in THF (10 mL). The progressof the reaction was monitored with TLC and after disappearance of the substrate (1.5 h) themixture was treated with aqueous, saturated ammonium chloride solution (7 mL) and extractedwith chloroform (4 10 mL). The combined organic phase was dried over magnesium sulfate andevaporated. The residue was separated on a silica gel column using DCM: ethyl acetate 2:1 and, nally,with ethyl acetate as eluents for diphenyl sulfoxide 9b (88 mg, 89%) m.p. 69-71 C; 1H NMR (CDCl3): = 7.22-7.36 (m, 6H), 7.47-7.62 (m, 4H) (these data are in accordance with literature data [35-37])and 1,2-O-isopropylidene--d-glucofuranose 13 (71 mg, 65% []D = 11.2 (c = 1.2, H2O- this valueis in accordance with literature data [38]). Substrate (+)-(R)-4 was not detected. A similar reaction of (+)-(R)-4 (0.133 g, 0.5 mmol) with p-toluenemagnesium bromide (1.5 mmol) aorded di-p-tolylsulfoxide 9c (92 mg, 80%) m.p. 92-94 C; 1H NMR (CDCl3): = 2.35, 7.25, and 7.52 (AB system,J = 7.2 Hz, 4H) (these data are in accordance with literature data [39]).
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