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[ CAS No. 488-82-4 ] {[proInfo.proName]}

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Chemical Structure| 488-82-4
Chemical Structure| 488-82-4
Structure of 488-82-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 488-82-4 ]

CAS No. :488-82-4 MDL No. :
Formula : C5H12O5 Boiling Point : -
Linear Structure Formula :- InChI Key :HEBKCHPVOIAQTA-QWWZWVQMSA-N
M.W : 152.15 Pubchem ID :94154
Synonyms :
D-Arabinitol;NSC 25288

Safety of [ 488-82-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 488-82-4 ]

* 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 [ 488-82-4 ]

[ 488-82-4 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 10323-20-3 ]
  • [ 488-82-4 ]
YieldReaction ConditionsOperation in experiment
After 24 hours a 50% conversion of D-arabitol may be obtained with a 95% selectivity to D-arabinose and D-lyxose.
palladium on charcoal; In hydrogen; EXAMPLE 4 Preparation of arabinitol Another aliquot of the arabinose solution obtained from Example 2 above is subjected to hydrogenation, in that hydrogen is passed into the solution after adding 10% palladium on charcoal thereto as a catalyst. After about 25 minutes the reaction is completed, and arabinitol is obtained by evaporation in vacuo in the form of white crystals.
  • 2
  • [ 1114-34-7 ]
  • [ 488-82-4 ]
YieldReaction ConditionsOperation in experiment
85% With sodium tetrahydroborate In water Reduction of D-lyxose to D-lyxitol To a solution of d-lyxose (1g) in water (10ml) was added an aqueous solution of sodium borohydride (0.2g/5ml H2O). When the reduction was complete the reaction mixture was acidified with a few drops of acetic acid, deionized with cation/anion ion-exchange resin and evaporated to dryness. Crystallization from methanol afforded d-lyxitol. Yield 85%
With sodium amalgam
With monospecific xylose reductase from yeast Candida intermedia; NADPH In phosphate buffer at 25℃;
  • 4
  • [ 488-82-4 ]
  • [ 106-95-6 ]
  • [ 81866-62-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide at 70 - 75℃; und weiteren Umsetzen des teilweise allylierten Produkts mit Natrium und Allylbromid;
  • 5
  • [ 2280-44-6 ]
  • [ 909878-64-4 ]
  • [ 488-82-4 ]
  • [ 1198-69-2 ]
  • [ 90-80-2 ]
YieldReaction ConditionsOperation in experiment
With 1-methyl-pyrrolidin-2-one; Wilkinson's catalyst at 130℃; for 6h; other unprotected aldose sugars; other rhodium-catalysts; var. temp. and reaction times;
  • 6
  • [ 133-99-3 ]
  • [ 909878-64-4 ]
  • [ 488-82-4 ]
  • [ 50-70-4 ]
  • [ 122795-46-4 ]
  • [ 63699-83-2 ]
  • [ 585-88-6 ]
  • 7
  • [ 488-82-4 ]
  • [ 3999-31-3 ]
YieldReaction ConditionsOperation in experiment
5 % Chromat. With hydrogenchloride In methanol at 85℃; for 24h;
  • 8
  • [ 154-17-6 ]
  • [ 64-18-6 ]
  • [ 488-82-4 ]
  • [ 5729-75-9 ]
  • 9
  • [ 154-17-6 ]
  • [ 64-18-6 ]
  • [ 488-82-4 ]
  • [ 5729-75-9 ]
  • [ 75754-51-7 ]
  • 10
  • [ 154-17-6 ]
  • [ 488-82-4 ]
  • [ 75754-51-7 ]
  • 11
  • [ 3445-24-7 ]
  • [ 488-82-4 ]
  • [ 488-81-3 ]
  • [ 488-84-6 ]
  • [ 50-69-1 ]
YieldReaction ConditionsOperation in experiment
70 % Chromat. With hydrogen In water at 80℃; for 0.5h;
  • 12
  • [ 488-82-4 ]
  • [ 108-24-7 ]
  • D-arabinitol pentaacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With iodine at 50℃; for 0.0833333h; Microwave irradiation; 2.3. Typical procedure for per-O-acetylation of D-glucose General procedure: To a 10.0 mL round bottom flask, D-glucose (2.0 mmol) and acetic anhydride (12.0 mmol, 1.2 equiv. per OH) in the IL400 (2.0mL) was added I2 (0.05 mmol) at room temperature. Then themixture was heated to 50 °C under MW irradiation (200 W) until the TLC analysis showed that the reaction was complete.Then the reaction mixture was cooled to room temperature,and toluene (2.0 mL × 3) was added. The mixture was vigorously stirred for several minutes and then kept stationary. The upper toluene layer containing the product was collected. Toluene was removed by a rotary evaporator, and the crude product was purified by recrystallization in ethyl alcohol. The desired peracetylated sugars were obtained in 90%-99% yields. The bottom phase was the ionic liquid containing the I2 catalyst and produced acetic acid. The I2/IL400 system was reused after the removal of the acetic acid under reduced pressure.
With sulfuric acid Yield given;
With pyridine
With dmap In pyridine for 24h; Ambient temperature;
With pyridine Yield given;
408 mg With pyridine; dmap at 20℃; for 2h;

  • 14
  • [ 81076-14-4 ]
  • [ 488-82-4 ]
YieldReaction ConditionsOperation in experiment
With Dowex 50X8-200 resin In water at 25℃; for 3h;
  • 15
  • (R)-2-((4S,5R)-5-Methoxymethoxy-2,2-dimethyl-[1,3]dioxan-4-yl)-1,4-dioxa-spiro[4.5]decane [ No CAS ]
  • [ 488-82-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In diethyl ether for 5h; Ambient temperature;
  • 16
  • [ 488-82-4 ]
  • [ 98-59-9 ]
  • [ 20703-96-2 ]
YieldReaction ConditionsOperation in experiment
75% With pyridine at 0℃; for 0.5h;
With pyridine at -10℃; for 1h;
  • 17
  • [ 488-82-4 ]
  • (2S,4S)-1,5-Dibromo-pentane-2,3,4-triol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Acetyl bromide In 1,4-dioxane at 20℃;
  • 18
  • [ 488-82-4 ]
  • [ 1005-56-7 ]
  • D-arabinitol-1,2:4,5-bis-thionocarbonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: D-Arabitol With di(n-butyl)tin oxide In toluene Stage #2: phenylcarbonochloridothioate In chloroform at 20℃; for 4h;
55% Stage #1: D-Arabitol With di(n-butyl)tin oxide In toluene Heating; Stage #2: phenylcarbonochloridothioate In chloroform at 20℃; for 4h;
  • 19
  • [ 488-30-2 ]
  • [ 909878-64-4 ]
  • [ 488-82-4 ]
  • [ 87-99-0 ]
  • [ 488-81-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In water at 80℃;
  • 20
  • [ 25636-49-1 ]
  • [ 488-82-4 ]
  • [ 457630-79-4 ]
YieldReaction ConditionsOperation in experiment
90% With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 38℃;
72% With camphorsulfonic acid In tetrahydrofuran
Acidic conditions;
  • 21
  • [ 488-82-4 ]
  • [ 87-99-0 ]
YieldReaction ConditionsOperation in experiment
98% for 27h; Microbiological reaction;
With potassium phosphate buffer; Gluconobacter oxydans ATCC 621 membrane fraction; Gluconobacter oxydans phosphate buffer-soluble fraction at 30℃; for 40h;
  • 22
  • [ 488-82-4 ]
  • Bis-((R)-2-oxo-2λ4-[1,3,2]dioxathiolan-4-yl)-methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With 1H-imidazole; thionyl chloride In tetrahydrofuran at -10℃; for 0.5h;
  • 23
  • [ 488-82-4 ]
  • [ 77-76-9 ]
  • [ 73543-86-9 ]
YieldReaction ConditionsOperation in experiment
37% With toluene-4-sulfonic acid In N,N-dimethyl-formamide; acetone at 20℃; for 10h;
With camphor-10-sulfonic acid In tetrahydrofuran for 0.25h; Reflux;
  • 24
  • [ 4143-61-7 ]
  • 2-3-dimethylethyl acetal of D-ribolactone [ No CAS ]
  • [ 23288-49-5 ]
  • [ 488-82-4 ]
  • [ 50-69-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium hydroxide; acetic acid; sodium sulfate; triphenylphosphine In tetrahydrofuran; methanol; dichloromethane; water 2 D-arabitol, 5-O-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenyl] and D-ribose, 5-O-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenyl] Example 2 D-arabitol, 5-O-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenyl] and D-ribose, 5-O-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenyl] Probucol (21 g, 40.4 mmol) was dissolved in THF (250 mL), and treated with the 2-3-dimethylethyl acetal of D-ribolactone (33.8 mmol, 6.9 g), triphenylphosphine (10.6 g, 40.4 mmol), and diethylazo-dicarboxylate (6.4 mL, 40.4 mmol). The reaction was refluxed for 3 h followed by evaporation of the solvent and chromatography (ether/hexane 20%-40%) to give 3.2 g (13.5%) of the intermediate lactone. The lactone (4.36 g) was dissolved in 100 ml of methanol, 10 ml of acetic acid and 2 mL of water. The reaction was refluxed 72 hours. The reaction solvents were evaporated and the resulting oil dissolved in methylene chloride, washed with 1 N NaOH, and water. The organic layer was dried over sodium sulfate and concentrated to yield 4 g of a white fluffy solid. The white fluffy solid was dissolved in 50 mL of THF and treated with 25 mL of 1N NaOH and stirred overnight at RT. The solvent was evaporated and the residue dissolved in methylene chloride and treated with 1N HCl to pH=7. The water layer was extracted with methylene chloride and then washed with water. The organic layer was dried over sodium sulfate, filtered, and concentrated to dryness to give 4.1 g of light green syrup. The light green syrup was dissolved in 150 mL of THF and 20 mL of 1M lithium aluminum hydride in ether was added at RT and stirred for 4 hours. The reaction was quenched with 50 mL of sat. sodium sulfate and stirred overnight. The organics were extracted with ether, dried over sodium sulfate and concentrated to dryness. The reaction products were purified by column chromatography (50% ether/hex to 100% ether). Three reaction products were separated and identified: 980 mg lactone, 600 mg lactol (15% yield; D-ribose, 5-O-[4-[[1-[[3,5-bis(1,1]-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1 -dimethylethyl)phenyl]), and 600 mg of alcohol (15% yield; D-arabitol, 5-O-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenyl]).
  • 25
  • [ 50-99-7 ]
  • [ 488-82-4 ]
YieldReaction ConditionsOperation in experiment
71% With pyridine In diethylene glycol dimethyl ether; N,N-dimethyl acetamide at 162℃; for 8h;
  • 26
  • [ 3458-28-4 ]
  • [ 3999-31-3 ]
  • [ 488-82-4 ]
YieldReaction ConditionsOperation in experiment
1: 72% 2: 20% With pyridine In diethylene glycol dimethyl ether; N,N-dimethyl acetamide at 162℃; for 8h;
  • 27
  • [ 59-23-4 ]
  • [ 488-82-4 ]
YieldReaction ConditionsOperation in experiment
56% With pyridine In diethylene glycol dimethyl ether; N,N-dimethyl acetamide at 162℃; for 8h;
  • 28
  • [ 488-82-4 ]
  • (R)-6-Benzyloxy-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-yl}-5-hydroxy-6-(R)-oxiranyl-hexan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: PPTS / CH2Cl2 2: CH2Cl2 3: 50 percent / NaH / dimethylformamide 4: 70 percent / BF3*THF; nBuLi 5: PdCl2(CH3CN)2 / CH2Cl2; H2O / 20 °C
  • 29
  • [ 488-82-4 ]
  • [ 909534-03-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: PPTS / CH2Cl2 2: CH2Cl2 3: 50 percent / NaH / dimethylformamide 4: 70 percent / BF3*THF; nBuLi 5: PdCl2(CH3CN)2 / CH2Cl2; H2O / 20 °C 6: imidazole / CH2Cl2
  • 30
  • [ 488-82-4 ]
  • [ 909534-04-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: PPTS / CH2Cl2 2: CH2Cl2 3: 50 percent / NaH / dimethylformamide 4: 70 percent / BF3*THF; nBuLi 5: PdCl2(CH3CN)2 / CH2Cl2; H2O / 20 °C 6: imidazole / CH2Cl2 7: NaBH4
  • 31
  • [ 488-82-4 ]
  • (2R,5R)-6-Benzyloxy-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-yl}-6-(R)-oxiranyl-5-triethylsilanyloxy-hexan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: PPTS / CH2Cl2 2: CH2Cl2 3: 50 percent / NaH / dimethylformamide 4: 70 percent / BF3*THF; nBuLi 5: PdCl2(CH3CN)2 / CH2Cl2; H2O / 20 °C 6: imidazole / CH2Cl2 7: NaBH4
  • 32
  • [ 488-82-4 ]
  • 4-Amino-benzoic acid (1S,4R)-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-ylmethyl}-5-hydroxy-5-(R)-oxiranyl-4-triethylsilanyloxy-pentyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: PPTS / CH2Cl2 2: CH2Cl2 3: 50 percent / NaH / dimethylformamide 4: 70 percent / BF3*THF; nBuLi 5: PdCl2(CH3CN)2 / CH2Cl2; H2O / 20 °C 6: imidazole / CH2Cl2 7: NaBH4 8: 83 percent / Et3N 9: 75 percent / H2 / Pd/C / toluene
  • 33
  • [ 488-82-4 ]
  • 4-Amino-benzoic acid (1R,4R)-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-ylmethyl}-5-hydroxy-5-(R)-oxiranyl-4-triethylsilanyloxy-pentyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: PPTS / CH2Cl2 2: CH2Cl2 3: 50 percent / NaH / dimethylformamide 4: 70 percent / BF3*THF; nBuLi 5: PdCl2(CH3CN)2 / CH2Cl2; H2O / 20 °C 6: imidazole / CH2Cl2 7: NaBH4 8: Et3N 9: H2 / Pd/C / toluene
  • 34
  • [ 488-82-4 ]
  • [ 909699-55-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: PPTS / CH2Cl2 2: CH2Cl2 3: 50 percent / NaH / dimethylformamide 4: 70 percent / BF3*THF; nBuLi 5: PdCl2(CH3CN)2 / CH2Cl2; H2O / 20 °C 6: imidazole / CH2Cl2 7: NaBH4 8: 83 percent / Et3N
  • 35
  • [ 488-82-4 ]
  • [ 909699-54-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: PPTS / CH2Cl2 2: CH2Cl2 3: 50 percent / NaH / dimethylformamide 4: 70 percent / BF3*THF; nBuLi 5: PdCl2(CH3CN)2 / CH2Cl2; H2O / 20 °C 6: imidazole / CH2Cl2 7: NaBH4 8: Et3N
  • 36
  • [ 488-82-4 ]
  • 1,5-anhydro-3-O-methyl-L-arabinitol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: 37 percent / p-toluenesulfonic acid monohydrate / dimethylformamide; acetone / 10 h / 20 °C 2.1: 86.6 percent / sodium hydroxide / H2O; dimethylsulfoxide 3.1: AcOH / H2O / 0.5 h / Heating 3.2: 90.7 percent / pyridine / 20 °C 4.1: 100 percent / sodium methoxide / methanol / 48 h / 20 °C 5.1: pyridine / 1 h / 20 °C 5.2: 20 °C 6.1: 1.43 g / sodium methoxide / methanol; CHCl3 / 0.5 h / 10 °C 7.1: 85 percent / water / (S,S)-(salen)Co(III)OAc / 48 h / 20 °C
  • 37
  • [ 488-82-4 ]
  • [ 570414-16-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: 91 percent / HCl / 18 h / 20 °C 2.1: 100 percent / Et3N; Bu2SnO / CH2Cl2 / 21 h / 20 °C 3.1: 91 percent / t-BuOK / tetrahydrofuran / 38 h / 20 °C 4.1: CuI / tetrahydrofuran; hexane / 0.5 h / -30 °C 4.2: 98 percent / tetrahydrofuran; hexane / 3 h / -20 °C 5.1: 93 percent / pyridine / 21 h / -40 - 20 °C 6.1: 100 percent / H2 / Pd(OH)2 / ethanol / 16 h / 20 °C / atmospheric pressure 7.1: 66 percent / NaN3 / dimethylformamide / 3 h / 95 °C
  • 38
  • [ 488-82-4 ]
  • [ 570414-15-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 91 percent / HCl / 18 h / 20 °C 2.1: 100 percent / Et3N; Bu2SnO / CH2Cl2 / 21 h / 20 °C 3.1: 91 percent / t-BuOK / tetrahydrofuran / 38 h / 20 °C 4.1: CuI / tetrahydrofuran; hexane / 0.5 h / -30 °C 4.2: 98 percent / tetrahydrofuran; hexane / 3 h / -20 °C 5.1: 93 percent / pyridine / 21 h / -40 - 20 °C 6.1: 100 percent / H2 / Pd(OH)2 / ethanol / 16 h / 20 °C / atmospheric pressure
  • 39
  • [ 488-82-4 ]
  • [ 383187-82-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1.1: 91 percent / HCl / 18 h / 20 °C 2.1: 100 percent / Et3N; Bu2SnO / CH2Cl2 / 21 h / 20 °C 3.1: 91 percent / t-BuOK / tetrahydrofuran / 38 h / 20 °C 4.1: CuI / tetrahydrofuran; hexane / 0.5 h / -30 °C 4.2: 98 percent / tetrahydrofuran; hexane / 3 h / -20 °C 5.1: 93 percent / pyridine / 21 h / -40 - 20 °C 6.1: 100 percent / H2 / Pd(OH)2 / ethanol / 16 h / 20 °C / atmospheric pressure 7.1: 66 percent / NaN3 / dimethylformamide / 3 h / 95 °C 8.1: p-TsOH*H2O / 2 h / 20 °C 8.2: 75 percent / methanol / 1 h / 20 °C 9.1: 68 percent / Bu4NBr / toluene; dimethylformamide / 120 h / 20 °C 10.1: 100 percent / H2 / Pd/CaCO3 / ethanol / 16 h / 20 °C / atmospheric pressure 11.1: EDCI; HOBt / dimethylformamide; CH2Cl2 / 0.5 h / 20 °C 11.2: 89 percent / i-Pr2NEt / dimethylformamide; CH2Cl2 / 16 h / 30 °C 12.1: aq. HCl / methanol; CH2Cl2; dioxane / 2 h / 20 °C 13.1: 46 mg / H2 / Pd(OH)2 / methanol; CHCl3 / 3 h / 20 °C / atmospheric pressure
Multi-step reaction with 13 steps 1.1: 91 percent / HCl / 18 h / 20 °C 2.1: 100 percent / Et3N; Bu2SnO / CH2Cl2 / 21 h / 20 °C 3.1: 91 percent / t-BuOK / tetrahydrofuran / 38 h / 20 °C 4.1: CuI / tetrahydrofuran; hexane / 0.5 h / -30 °C 4.2: 98 percent / tetrahydrofuran; hexane / 3 h / -20 °C 5.1: 93 percent / pyridine / 21 h / -40 - 20 °C 6.1: 100 percent / H2 / Pd(OH)2 / ethanol / 16 h / 20 °C / atmospheric pressure 7.1: 66 percent / NaN3 / dimethylformamide / 3 h / 95 °C 8.1: p-TsOH*H2O / 2 h / 20 °C 8.2: 75 percent / methanol / 1 h / 20 °C 9.1: 57 percent / BF3*OEt2 / CHCl3 / 14 h / -50 °C 10.1: 100 percent / H2 / Pd/CaCO3 / ethanol / 16 h / 20 °C / atmospheric pressure 11.1: EDCI; HOBt / dimethylformamide; CH2Cl2 / 0.5 h / 20 °C 11.2: 89 percent / i-Pr2NEt / dimethylformamide; CH2Cl2 / 16 h / 30 °C 12.1: aq. HCl / methanol; CH2Cl2; dioxane / 2 h / 20 °C 13.1: 46 mg / H2 / Pd(OH)2 / methanol; CHCl3 / 3 h / 20 °C / atmospheric pressure
  • 40
  • [ 488-82-4 ]
  • [ 745041-56-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: 91 percent / HCl / 18 h / 20 °C 2.1: 100 percent / Et3N; Bu2SnO / CH2Cl2 / 21 h / 20 °C 3.1: 91 percent / t-BuOK / tetrahydrofuran / 38 h / 20 °C 4.1: CuI / tetrahydrofuran; hexane / 0.5 h / -30 °C 4.2: 98 percent / tetrahydrofuran; hexane / 3 h / -20 °C 5.1: 93 percent / pyridine / 21 h / -40 - 20 °C 6.1: 100 percent / H2 / Pd(OH)2 / ethanol / 16 h / 20 °C / atmospheric pressure 7.1: 66 percent / NaN3 / dimethylformamide / 3 h / 95 °C 8.1: p-TsOH*H2O / 2 h / 20 °C 8.2: 75 percent / methanol / 1 h / 20 °C
  • 41
  • [ 488-82-4 ]
  • [ 745041-72-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: 91 percent / HCl / 18 h / 20 °C 2.1: 100 percent / Et3N; Bu2SnO / CH2Cl2 / 21 h / 20 °C 3.1: 91 percent / t-BuOK / tetrahydrofuran / 38 h / 20 °C 4.1: CuI / tetrahydrofuran; hexane / 0.5 h / -30 °C 4.2: 98 percent / tetrahydrofuran; hexane / 3 h / -20 °C 5.1: 93 percent / pyridine / 21 h / -40 - 20 °C 6.1: 100 percent / H2 / Pd(OH)2 / ethanol / 16 h / 20 °C / atmospheric pressure 7.1: 66 percent / NaN3 / dimethylformamide / 3 h / 95 °C 8.1: p-TsOH*H2O / 2 h / 20 °C 8.2: 75 percent / methanol / 1 h / 20 °C 9.1: 68 percent / Bu4NBr / toluene; dimethylformamide / 120 h / 20 °C 10.1: 100 percent / H2 / Pd/CaCO3 / ethanol / 16 h / 20 °C / atmospheric pressure
Multi-step reaction with 10 steps 1.1: 91 percent / HCl / 18 h / 20 °C 2.1: 100 percent / Et3N; Bu2SnO / CH2Cl2 / 21 h / 20 °C 3.1: 91 percent / t-BuOK / tetrahydrofuran / 38 h / 20 °C 4.1: CuI / tetrahydrofuran; hexane / 0.5 h / -30 °C 4.2: 98 percent / tetrahydrofuran; hexane / 3 h / -20 °C 5.1: 93 percent / pyridine / 21 h / -40 - 20 °C 6.1: 100 percent / H2 / Pd(OH)2 / ethanol / 16 h / 20 °C / atmospheric pressure 7.1: 66 percent / NaN3 / dimethylformamide / 3 h / 95 °C 8.1: p-TsOH*H2O / 2 h / 20 °C 8.2: 75 percent / methanol / 1 h / 20 °C 9.1: 57 percent / BF3*OEt2 / CHCl3 / 14 h / -50 °C 10.1: 100 percent / H2 / Pd/CaCO3 / ethanol / 16 h / 20 °C / atmospheric pressure
  • 42
  • [ 488-82-4 ]
  • (2S,3S,4R)-2-azido-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-1,3,4-nonanetriol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: 91 percent / HCl / 18 h / 20 °C 2.1: 100 percent / Et3N; Bu2SnO / CH2Cl2 / 21 h / 20 °C 3.1: 91 percent / t-BuOK / tetrahydrofuran / 38 h / 20 °C 4.1: CuI / tetrahydrofuran; hexane / 0.5 h / -30 °C 4.2: 98 percent / tetrahydrofuran; hexane / 3 h / -20 °C 5.1: 93 percent / pyridine / 21 h / -40 - 20 °C 6.1: 100 percent / H2 / Pd(OH)2 / ethanol / 16 h / 20 °C / atmospheric pressure 7.1: 66 percent / NaN3 / dimethylformamide / 3 h / 95 °C 8.1: p-TsOH*H2O / 2 h / 20 °C 8.2: 75 percent / methanol / 1 h / 20 °C 9.1: 25 percent / BF3*OEt2 / CHCl3 / 14 h / -50 °C
  • 43
  • [ 488-82-4 ]
  • [ 745041-64-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: 91 percent / HCl / 18 h / 20 °C 2.1: 100 percent / Et3N; Bu2SnO / CH2Cl2 / 21 h / 20 °C 3.1: 91 percent / t-BuOK / tetrahydrofuran / 38 h / 20 °C 4.1: CuI / tetrahydrofuran; hexane / 0.5 h / -30 °C 4.2: 98 percent / tetrahydrofuran; hexane / 3 h / -20 °C 5.1: 93 percent / pyridine / 21 h / -40 - 20 °C 6.1: 100 percent / H2 / Pd(OH)2 / ethanol / 16 h / 20 °C / atmospheric pressure 7.1: 66 percent / NaN3 / dimethylformamide / 3 h / 95 °C 8.1: p-TsOH*H2O / 2 h / 20 °C 8.2: 75 percent / methanol / 1 h / 20 °C 9.1: 68 percent / Bu4NBr / toluene; dimethylformamide / 120 h / 20 °C
Multi-step reaction with 9 steps 1.1: 91 percent / HCl / 18 h / 20 °C 2.1: 100 percent / Et3N; Bu2SnO / CH2Cl2 / 21 h / 20 °C 3.1: 91 percent / t-BuOK / tetrahydrofuran / 38 h / 20 °C 4.1: CuI / tetrahydrofuran; hexane / 0.5 h / -30 °C 4.2: 98 percent / tetrahydrofuran; hexane / 3 h / -20 °C 5.1: 93 percent / pyridine / 21 h / -40 - 20 °C 6.1: 100 percent / H2 / Pd(OH)2 / ethanol / 16 h / 20 °C / atmospheric pressure 7.1: 66 percent / NaN3 / dimethylformamide / 3 h / 95 °C 8.1: p-TsOH*H2O / 2 h / 20 °C 8.2: 75 percent / methanol / 1 h / 20 °C 9.1: 57 percent / BF3*OEt2 / CHCl3 / 14 h / -50 °C
  • 44
  • [ 488-82-4 ]
  • [ 745041-79-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1.1: 91 percent / HCl / 18 h / 20 °C 2.1: 100 percent / Et3N; Bu2SnO / CH2Cl2 / 21 h / 20 °C 3.1: 91 percent / t-BuOK / tetrahydrofuran / 38 h / 20 °C 4.1: CuI / tetrahydrofuran; hexane / 0.5 h / -30 °C 4.2: 98 percent / tetrahydrofuran; hexane / 3 h / -20 °C 5.1: 93 percent / pyridine / 21 h / -40 - 20 °C 6.1: 100 percent / H2 / Pd(OH)2 / ethanol / 16 h / 20 °C / atmospheric pressure 7.1: 66 percent / NaN3 / dimethylformamide / 3 h / 95 °C 8.1: p-TsOH*H2O / 2 h / 20 °C 8.2: 75 percent / methanol / 1 h / 20 °C 9.1: 68 percent / Bu4NBr / toluene; dimethylformamide / 120 h / 20 °C 10.1: 100 percent / H2 / Pd/CaCO3 / ethanol / 16 h / 20 °C / atmospheric pressure 11.1: EDCI; HOBt / dimethylformamide; CH2Cl2 / 0.5 h / 20 °C 11.2: 89 percent / i-Pr2NEt / dimethylformamide; CH2Cl2 / 16 h / 30 °C
Multi-step reaction with 11 steps 1.1: 91 percent / HCl / 18 h / 20 °C 2.1: 100 percent / Et3N; Bu2SnO / CH2Cl2 / 21 h / 20 °C 3.1: 91 percent / t-BuOK / tetrahydrofuran / 38 h / 20 °C 4.1: CuI / tetrahydrofuran; hexane / 0.5 h / -30 °C 4.2: 98 percent / tetrahydrofuran; hexane / 3 h / -20 °C 5.1: 93 percent / pyridine / 21 h / -40 - 20 °C 6.1: 100 percent / H2 / Pd(OH)2 / ethanol / 16 h / 20 °C / atmospheric pressure 7.1: 66 percent / NaN3 / dimethylformamide / 3 h / 95 °C 8.1: p-TsOH*H2O / 2 h / 20 °C 8.2: 75 percent / methanol / 1 h / 20 °C 9.1: 57 percent / BF3*OEt2 / CHCl3 / 14 h / -50 °C 10.1: 100 percent / H2 / Pd/CaCO3 / ethanol / 16 h / 20 °C / atmospheric pressure 11.1: EDCI; HOBt / dimethylformamide; CH2Cl2 / 0.5 h / 20 °C 11.2: 89 percent / i-Pr2NEt / dimethylformamide; CH2Cl2 / 16 h / 30 °C
  • 45
  • [ 488-82-4 ]
  • [ 745042-02-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1.1: 91 percent / HCl / 18 h / 20 °C 2.1: 100 percent / Et3N; Bu2SnO / CH2Cl2 / 21 h / 20 °C 3.1: 91 percent / t-BuOK / tetrahydrofuran / 38 h / 20 °C 4.1: CuI / tetrahydrofuran; hexane / 0.5 h / -30 °C 4.2: 98 percent / tetrahydrofuran; hexane / 3 h / -20 °C 5.1: 93 percent / pyridine / 21 h / -40 - 20 °C 6.1: 100 percent / H2 / Pd(OH)2 / ethanol / 16 h / 20 °C / atmospheric pressure 7.1: 66 percent / NaN3 / dimethylformamide / 3 h / 95 °C 8.1: p-TsOH*H2O / 2 h / 20 °C 8.2: 75 percent / methanol / 1 h / 20 °C 9.1: 68 percent / Bu4NBr / toluene; dimethylformamide / 120 h / 20 °C 10.1: 100 percent / H2 / Pd/CaCO3 / ethanol / 16 h / 20 °C / atmospheric pressure 11.1: EDCI; HOBt / dimethylformamide; CH2Cl2 / 0.5 h / 20 °C 11.2: 89 percent / i-Pr2NEt / dimethylformamide; CH2Cl2 / 16 h / 30 °C 12.1: aq. HCl / methanol; CH2Cl2; dioxane / 2 h / 20 °C
Multi-step reaction with 12 steps 1.1: 91 percent / HCl / 18 h / 20 °C 2.1: 100 percent / Et3N; Bu2SnO / CH2Cl2 / 21 h / 20 °C 3.1: 91 percent / t-BuOK / tetrahydrofuran / 38 h / 20 °C 4.1: CuI / tetrahydrofuran; hexane / 0.5 h / -30 °C 4.2: 98 percent / tetrahydrofuran; hexane / 3 h / -20 °C 5.1: 93 percent / pyridine / 21 h / -40 - 20 °C 6.1: 100 percent / H2 / Pd(OH)2 / ethanol / 16 h / 20 °C / atmospheric pressure 7.1: 66 percent / NaN3 / dimethylformamide / 3 h / 95 °C 8.1: p-TsOH*H2O / 2 h / 20 °C 8.2: 75 percent / methanol / 1 h / 20 °C 9.1: 57 percent / BF3*OEt2 / CHCl3 / 14 h / -50 °C 10.1: 100 percent / H2 / Pd/CaCO3 / ethanol / 16 h / 20 °C / atmospheric pressure 11.1: EDCI; HOBt / dimethylformamide; CH2Cl2 / 0.5 h / 20 °C 11.2: 89 percent / i-Pr2NEt / dimethylformamide; CH2Cl2 / 16 h / 30 °C 12.1: aq. HCl / methanol; CH2Cl2; dioxane / 2 h / 20 °C
  • 46
  • [ 488-82-4 ]
  • (3Z,5E,14E)-(9S,10S,12S,13S,19S,20R)-9,10,12,13-Tetrahydroxy-4,19-dimethyl-20-[(2R,3S)-3-((S)-1-methyl-butyl)-oxiranyl]-8,11,17-trimethylene-oxacycloicosa-3,5,14-trien-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 20 steps 1.1: 90 percent / CSA / dimethylformamide / 38 °C 2.1: SO3*pyridine; i-Pr2NEt / dimethylsulfoxide / 1 h / 20 °C 3.1: NaHMDS / 0 - 20 °C 3.2: 4 h / 0 °C 4.1: CSA; H2O / methanol; CH2Cl2 / 7 h / 40 °C 5.1: imidazole; DMAP / dimethylformamide; CH2Cl2 / 12 h / 20 °C 6.1: 38 percent / CSA / 48 h / 40 °C 7.1: TBAF / tetrahydrofuran / 1.5 h 8.1: pyridine / CH2Cl2 / 0 - 20 °C 9.1: 98 percent / DMP; pyridine / CH2Cl2 10.1: t-BuLi; MgBr2*Et2O / benzene / 25 h / -78 - 20 °C 10.2: 70 percent / MgBr2*Et2O / CH2Cl2; benzene / 0.75 h / 0 °C 11.1: 81 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 88 percent / super-hydride / tetrahydrofuran / 0.58 h / 0 °C 13.1: 98 percent / DMP / pyridine / 1.5 h / 20 °C 14.1: MgBr2*Et2O / CH2Cl2; benzene 14.2: 60 percent / CH2Cl2; benzene; tetrahydrofuran / 1 h / 0 °C 15.1: 92 percent / NBS; AgNO3 / acetone / 20 °C 16.1: Bu3SnF; Red-Sil; TBAF / (PPh3)2PdCl2 / diethyl ether / 2.5 h / 20 °C 16.2: Cu(I) thiophenecarboxylate; NMP / 0 - 20 °C 17.1: PhHC=Ru(PCy3)(IMes-H2)Cl2 / CH2Cl2 / 40 °C 18.1: 2,6-lutidine / CH2Cl2 / 0 °C 19.1: DDQ / 2-methyl-propan-2-ol; CH2Cl2; various solvent(s) / 20 °C / pH 7 20.1: TBAF; AcOH / tetrahydrofuran / 20 °C
  • 47
  • [ 488-82-4 ]
  • (3E,5E,14E)-(9S,10S,12S,13S,19S,20R)-9,10,12,13-Tetrahydroxy-4,19-dimethyl-20-[(2R,3S)-3-((S)-1-methyl-butyl)-oxiranyl]-8,11,17-trimethylene-oxacycloicosa-3,5,14-trien-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 20 steps 1.1: 90 percent / CSA / dimethylformamide / 38 °C 2.1: SO3*pyridine; i-Pr2NEt / dimethylsulfoxide / 1 h / 20 °C 3.1: NaHMDS / 0 - 20 °C 3.2: 4 h / 0 °C 4.1: CSA; H2O / methanol; CH2Cl2 / 7 h / 40 °C 5.1: imidazole; DMAP / dimethylformamide; CH2Cl2 / 12 h / 20 °C 6.1: 38 percent / CSA / 48 h / 40 °C 7.1: TBAF / tetrahydrofuran / 1.5 h 8.1: pyridine / CH2Cl2 / 0 - 20 °C 9.1: 98 percent / DMP; pyridine / CH2Cl2 10.1: t-BuLi; MgBr2*Et2O / benzene / 25 h / -78 - 20 °C 10.2: 70 percent / MgBr2*Et2O / CH2Cl2; benzene / 0.75 h / 0 °C 11.1: 81 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 88 percent / super-hydride / tetrahydrofuran / 0.58 h / 0 °C 13.1: 98 percent / DMP / pyridine / 1.5 h / 20 °C 14.1: MgBr2*Et2O / CH2Cl2; benzene 14.2: 60 percent / CH2Cl2; benzene; tetrahydrofuran / 1 h / 0 °C 15.1: 92 percent / NBS; AgNO3 / acetone / 20 °C 16.1: Bu3SnF; Red-Sil; TBAF / (PPh3)2PdCl2 / diethyl ether / 2.5 h / 20 °C 16.2: Cu(I) thiophenecarboxylate; NMP / 0.75 h / 0 - 20 °C 17.1: 35 percent / PhHC=Ru(PCy3)(IMes-H2)Cl2 / CH2Cl2 / 24 h / 40 °C 18.1: 92 percent / 2,6-lutidine / CH2Cl2 / 1.25 h / 0 °C 19.1: 52 percent / DDQ / 2-methyl-propan-2-ol; CH2Cl2; various solvent(s) / 4 h / 20 °C / pH 7 20.1: 25 percent / TBAF; AcOH / tetrahydrofuran / 21 h / 20 °C
  • 48
  • [ 488-82-4 ]
  • (2S,4S)-3-methylenepentane-1,2,4,5-tetraol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 90 percent / CSA / dimethylformamide / 38 °C 2.1: SO3*pyridine; i-Pr2NEt / dimethylsulfoxide / 1 h / 20 °C 3.1: NaHMDS / 0 - 20 °C 3.2: 4 h / 0 °C 4.1: CSA; H2O / methanol; CH2Cl2 / 7 h / 40 °C
Multi-step reaction with 4 steps 1: camphorsulfonic acid / tetrahydrofuran 2: sulfur trioxide pyridine complex; dimethyl sulfoxide 3: sodium hexamethyldisilazane 4: camphorsulfonic acid / methanol; dichloromethane / 16 h / Reflux
  • 49
  • [ 488-82-4 ]
  • Bis-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / CSA / dimethylformamide / 38 °C 2: SO3*pyridine; i-Pr2NEt / dimethylsulfoxide / 1 h / 20 °C
Multi-step reaction with 2 steps 1: camphorsulfonic acid / tetrahydrofuran 2: sulfur trioxide pyridine complex; dimethyl sulfoxide
  • 50
  • [ 488-82-4 ]
  • [ 457630-80-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 90 percent / CSA / dimethylformamide / 38 °C 2.1: SO3*pyridine; i-Pr2NEt / dimethylsulfoxide / 1 h / 20 °C 3.1: NaHMDS / 0 - 20 °C 3.2: 4 h / 0 °C
Multi-step reaction with 3 steps 1: camphorsulfonic acid / tetrahydrofuran 2: sulfur trioxide pyridine complex; dimethyl sulfoxide 3: sodium hexamethyldisilazane
  • 51
  • [ 488-82-4 ]
  • (3Z,5E,14E)-(9S,10S,12S,19S,20R)-9,13-Bis-(tert-butyl-dimethyl-silanyloxy)-10,12-dihydroxy-4,19-dimethyl-20-[(2R,3S)-3-((S)-1-methyl-butyl)-oxiranyl]-8,11,17-trimethylene-oxacycloicosa-3,5,14-trien-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 19 steps 1.1: 90 percent / CSA / dimethylformamide / 38 °C 2.1: SO3*pyridine; i-Pr2NEt / dimethylsulfoxide / 1 h / 20 °C 3.1: NaHMDS / 0 - 20 °C 3.2: 4 h / 0 °C 4.1: CSA; H2O / methanol; CH2Cl2 / 7 h / 40 °C 5.1: imidazole; DMAP / dimethylformamide; CH2Cl2 / 12 h / 20 °C 6.1: 38 percent / CSA / 48 h / 40 °C 7.1: TBAF / tetrahydrofuran / 1.5 h 8.1: pyridine / CH2Cl2 / 0 - 20 °C 9.1: 98 percent / DMP; pyridine / CH2Cl2 10.1: t-BuLi; MgBr2*Et2O / benzene / 25 h / -78 - 20 °C 10.2: 70 percent / MgBr2*Et2O / CH2Cl2; benzene / 0.75 h / 0 °C 11.1: 81 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 88 percent / super-hydride / tetrahydrofuran / 0.58 h / 0 °C 13.1: 98 percent / DMP / pyridine / 1.5 h / 20 °C 14.1: MgBr2*Et2O / CH2Cl2; benzene 14.2: 60 percent / CH2Cl2; benzene; tetrahydrofuran / 1 h / 0 °C 15.1: 92 percent / NBS; AgNO3 / acetone / 20 °C 16.1: Bu3SnF; Red-Sil; TBAF / (PPh3)2PdCl2 / diethyl ether / 2.5 h / 20 °C 16.2: Cu(I) thiophenecarboxylate; NMP / 0 - 20 °C 17.1: PhHC=Ru(PCy3)(IMes-H2)Cl2 / CH2Cl2 / 40 °C 18.1: 2,6-lutidine / CH2Cl2 / 0 °C 19.1: DDQ / 2-methyl-propan-2-ol; CH2Cl2; various solvent(s) / 20 °C / pH 7
  • 52
  • [ 488-82-4 ]
  • (3E,5E,14E)-(9S,10S,12S,19S,20R)-9,13-Bis-(tert-butyl-dimethyl-silanyloxy)-10,12-dihydroxy-4,19-dimethyl-20-[(2R,3S)-3-((S)-1-methyl-butyl)-oxiranyl]-8,11,17-trimethylene-oxacycloicosa-3,5,14-trien-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 19 steps 1.1: 90 percent / CSA / dimethylformamide / 38 °C 2.1: SO3*pyridine; i-Pr2NEt / dimethylsulfoxide / 1 h / 20 °C 3.1: NaHMDS / 0 - 20 °C 3.2: 4 h / 0 °C 4.1: CSA; H2O / methanol; CH2Cl2 / 7 h / 40 °C 5.1: imidazole; DMAP / dimethylformamide; CH2Cl2 / 12 h / 20 °C 6.1: 38 percent / CSA / 48 h / 40 °C 7.1: TBAF / tetrahydrofuran / 1.5 h 8.1: pyridine / CH2Cl2 / 0 - 20 °C 9.1: 98 percent / DMP; pyridine / CH2Cl2 10.1: t-BuLi; MgBr2*Et2O / benzene / 25 h / -78 - 20 °C 10.2: 70 percent / MgBr2*Et2O / CH2Cl2; benzene / 0.75 h / 0 °C 11.1: 81 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 88 percent / super-hydride / tetrahydrofuran / 0.58 h / 0 °C 13.1: 98 percent / DMP / pyridine / 1.5 h / 20 °C 14.1: MgBr2*Et2O / CH2Cl2; benzene 14.2: 60 percent / CH2Cl2; benzene; tetrahydrofuran / 1 h / 0 °C 15.1: 92 percent / NBS; AgNO3 / acetone / 20 °C 16.1: Bu3SnF; Red-Sil; TBAF / (PPh3)2PdCl2 / diethyl ether / 2.5 h / 20 °C 16.2: Cu(I) thiophenecarboxylate; NMP / 0.75 h / 0 - 20 °C 17.1: 35 percent / PhHC=Ru(PCy3)(IMes-H2)Cl2 / CH2Cl2 / 24 h / 40 °C 18.1: 92 percent / 2,6-lutidine / CH2Cl2 / 1.25 h / 0 °C 19.1: 52 percent / DDQ / 2-methyl-propan-2-ol; CH2Cl2; various solvent(s) / 4 h / 20 °C / pH 7
  • 53
  • [ 488-82-4 ]
  • (3Z,5E,14E)-(9S,10S,12S,19S,20R)-9-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-10,12-bis-(4-methoxy-benzyloxy)-4,19-dimethyl-20-[(2R,3S)-3-((S)-1-methyl-butyl)-oxiranyl]-8,11,17-trimethylene-oxacycloicosa-3,5,14-trien-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 17 steps 1.1: 90 percent / CSA / dimethylformamide / 38 °C 2.1: SO3*pyridine; i-Pr2NEt / dimethylsulfoxide / 1 h / 20 °C 3.1: NaHMDS / 0 - 20 °C 3.2: 4 h / 0 °C 4.1: CSA; H2O / methanol; CH2Cl2 / 7 h / 40 °C 5.1: imidazole; DMAP / dimethylformamide; CH2Cl2 / 12 h / 20 °C 6.1: 38 percent / CSA / 48 h / 40 °C 7.1: TBAF / tetrahydrofuran / 1.5 h 8.1: pyridine / CH2Cl2 / 0 - 20 °C 9.1: 98 percent / DMP; pyridine / CH2Cl2 10.1: t-BuLi; MgBr2*Et2O / benzene / 25 h / -78 - 20 °C 10.2: 70 percent / MgBr2*Et2O / CH2Cl2; benzene / 0.75 h / 0 °C 11.1: 81 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 88 percent / super-hydride / tetrahydrofuran / 0.58 h / 0 °C 13.1: 98 percent / DMP / pyridine / 1.5 h / 20 °C 14.1: MgBr2*Et2O / CH2Cl2; benzene 14.2: 60 percent / CH2Cl2; benzene; tetrahydrofuran / 1 h / 0 °C 15.1: 92 percent / NBS; AgNO3 / acetone / 20 °C 16.1: Bu3SnF; Red-Sil; TBAF / (PPh3)2PdCl2 / diethyl ether / 2.5 h / 20 °C 16.2: Cu(I) thiophenecarboxylate; NMP / 0 - 20 °C 17.1: PhHC=Ru(PCy3)(IMes-H2)Cl2 / CH2Cl2 / 40 °C
  • 54
  • [ 488-82-4 ]
  • (3E,5E,14E)-(9S,10S,12S,19S,20R)-9-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-10,12-bis-(4-methoxy-benzyloxy)-4,19-dimethyl-20-[(2R,3S)-3-((S)-1-methyl-butyl)-oxiranyl]-8,11,17-trimethylene-oxacycloicosa-3,5,14-trien-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 17 steps 1.1: 90 percent / CSA / dimethylformamide / 38 °C 2.1: SO3*pyridine; i-Pr2NEt / dimethylsulfoxide / 1 h / 20 °C 3.1: NaHMDS / 0 - 20 °C 3.2: 4 h / 0 °C 4.1: CSA; H2O / methanol; CH2Cl2 / 7 h / 40 °C 5.1: imidazole; DMAP / dimethylformamide; CH2Cl2 / 12 h / 20 °C 6.1: 38 percent / CSA / 48 h / 40 °C 7.1: TBAF / tetrahydrofuran / 1.5 h 8.1: pyridine / CH2Cl2 / 0 - 20 °C 9.1: 98 percent / DMP; pyridine / CH2Cl2 10.1: t-BuLi; MgBr2*Et2O / benzene / 25 h / -78 - 20 °C 10.2: 70 percent / MgBr2*Et2O / CH2Cl2; benzene / 0.75 h / 0 °C 11.1: 81 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 88 percent / super-hydride / tetrahydrofuran / 0.58 h / 0 °C 13.1: 98 percent / DMP / pyridine / 1.5 h / 20 °C 14.1: MgBr2*Et2O / CH2Cl2; benzene 14.2: 60 percent / CH2Cl2; benzene; tetrahydrofuran / 1 h / 0 °C 15.1: 92 percent / NBS; AgNO3 / acetone / 20 °C 16.1: Bu3SnF; Red-Sil; TBAF / (PPh3)2PdCl2 / diethyl ether / 2.5 h / 20 °C 16.2: Cu(I) thiophenecarboxylate; NMP / 0.75 h / 0 - 20 °C 17.1: 35 percent / PhHC=Ru(PCy3)(IMes-H2)Cl2 / CH2Cl2 / 24 h / 40 °C
  • 55
  • [ 488-82-4 ]
  • (2Z,4E)-(8S,9S,11S)-8-(tert-Butyl-dimethyl-silanyloxy)-12-hydroxy-9,11-bis-(4-methoxy-benzyloxy)-3-methyl-7,10-dimethylene-tetradeca-2,4,13-trienoic acid (1R,2S)-2-methyl-1-[(2R,3S)-3-((S)-1-methyl-butyl)-oxiranyl]-4-methylene-hept-6-enyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 16 steps 1.1: 90 percent / CSA / dimethylformamide / 38 °C 2.1: SO3*pyridine; i-Pr2NEt / dimethylsulfoxide / 1 h / 20 °C 3.1: NaHMDS / 0 - 20 °C 3.2: 4 h / 0 °C 4.1: CSA; H2O / methanol; CH2Cl2 / 7 h / 40 °C 5.1: imidazole; DMAP / dimethylformamide; CH2Cl2 / 12 h / 20 °C 6.1: 38 percent / CSA / 48 h / 40 °C 7.1: TBAF / tetrahydrofuran / 1.5 h 8.1: pyridine / CH2Cl2 / 0 - 20 °C 9.1: 98 percent / DMP; pyridine / CH2Cl2 10.1: t-BuLi; MgBr2*Et2O / benzene / 25 h / -78 - 20 °C 10.2: 70 percent / MgBr2*Et2O / CH2Cl2; benzene / 0.75 h / 0 °C 11.1: 81 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 88 percent / super-hydride / tetrahydrofuran / 0.58 h / 0 °C 13.1: 98 percent / DMP / pyridine / 1.5 h / 20 °C 14.1: MgBr2*Et2O / CH2Cl2; benzene 14.2: 60 percent / CH2Cl2; benzene; tetrahydrofuran / 1 h / 0 °C 15.1: 92 percent / NBS; AgNO3 / acetone / 20 °C 16.1: Bu3SnF; Red-Sil; TBAF / (PPh3)2PdCl2 / diethyl ether / 2.5 h / 20 °C 16.2: Cu(I) thiophenecarboxylate; NMP / 0 - 20 °C
  • 56
  • [ 488-82-4 ]
  • (2E,4E)-(8S,9S,11S)-8-(tert-Butyl-dimethyl-silanyloxy)-12-hydroxy-9,11-bis-(4-methoxy-benzyloxy)-3-methyl-7,10-dimethylene-tetradeca-2,4,13-trienoic acid (1R,2S)-2-methyl-1-[(2R,3S)-3-((S)-1-methyl-butyl)-oxiranyl]-4-methylene-hept-6-enyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 16 steps 1.1: 90 percent / CSA / dimethylformamide / 38 °C 2.1: SO3*pyridine; i-Pr2NEt / dimethylsulfoxide / 1 h / 20 °C 3.1: NaHMDS / 0 - 20 °C 3.2: 4 h / 0 °C 4.1: CSA; H2O / methanol; CH2Cl2 / 7 h / 40 °C 5.1: imidazole; DMAP / dimethylformamide; CH2Cl2 / 12 h / 20 °C 6.1: 38 percent / CSA / 48 h / 40 °C 7.1: TBAF / tetrahydrofuran / 1.5 h 8.1: pyridine / CH2Cl2 / 0 - 20 °C 9.1: 98 percent / DMP; pyridine / CH2Cl2 10.1: t-BuLi; MgBr2*Et2O / benzene / 25 h / -78 - 20 °C 10.2: 70 percent / MgBr2*Et2O / CH2Cl2; benzene / 0.75 h / 0 °C 11.1: 81 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 88 percent / super-hydride / tetrahydrofuran / 0.58 h / 0 °C 13.1: 98 percent / DMP / pyridine / 1.5 h / 20 °C 14.1: MgBr2*Et2O / CH2Cl2; benzene 14.2: 60 percent / CH2Cl2; benzene; tetrahydrofuran / 1 h / 0 °C 15.1: 92 percent / NBS; AgNO3 / acetone / 20 °C 16.1: Bu3SnF; Red-Sil; TBAF / (PPh3)2PdCl2 / diethyl ether / 2.5 h / 20 °C 16.2: Cu(I) thiophenecarboxylate; NMP / 0.75 h / 0 - 20 °C
  • 57
  • [ 488-82-4 ]
  • (3Z,5E,14E)-(9S,10S,12S,19S,20R)-9,13-Bis-(tert-butyl-dimethyl-silanyloxy)-10,12-bis-(4-methoxy-benzyloxy)-4,19-dimethyl-20-[(2R,3S)-3-((S)-1-methyl-butyl)-oxiranyl]-8,11,17-trimethylene-oxacycloicosa-3,5,14-trien-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 18 steps 1.1: 90 percent / CSA / dimethylformamide / 38 °C 2.1: SO3*pyridine; i-Pr2NEt / dimethylsulfoxide / 1 h / 20 °C 3.1: NaHMDS / 0 - 20 °C 3.2: 4 h / 0 °C 4.1: CSA; H2O / methanol; CH2Cl2 / 7 h / 40 °C 5.1: imidazole; DMAP / dimethylformamide; CH2Cl2 / 12 h / 20 °C 6.1: 38 percent / CSA / 48 h / 40 °C 7.1: TBAF / tetrahydrofuran / 1.5 h 8.1: pyridine / CH2Cl2 / 0 - 20 °C 9.1: 98 percent / DMP; pyridine / CH2Cl2 10.1: t-BuLi; MgBr2*Et2O / benzene / 25 h / -78 - 20 °C 10.2: 70 percent / MgBr2*Et2O / CH2Cl2; benzene / 0.75 h / 0 °C 11.1: 81 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 88 percent / super-hydride / tetrahydrofuran / 0.58 h / 0 °C 13.1: 98 percent / DMP / pyridine / 1.5 h / 20 °C 14.1: MgBr2*Et2O / CH2Cl2; benzene 14.2: 60 percent / CH2Cl2; benzene; tetrahydrofuran / 1 h / 0 °C 15.1: 92 percent / NBS; AgNO3 / acetone / 20 °C 16.1: Bu3SnF; Red-Sil; TBAF / (PPh3)2PdCl2 / diethyl ether / 2.5 h / 20 °C 16.2: Cu(I) thiophenecarboxylate; NMP / 0 - 20 °C 17.1: PhHC=Ru(PCy3)(IMes-H2)Cl2 / CH2Cl2 / 40 °C 18.1: 2,6-lutidine / CH2Cl2 / 0 °C
  • 58
  • [ 488-82-4 ]
  • (3E,5E,14E)-(9S,10S,12S,19S,20R)-9,13-Bis-(tert-butyl-dimethyl-silanyloxy)-10,12-bis-(4-methoxy-benzyloxy)-4,19-dimethyl-20-[(2R,3S)-3-((S)-1-methyl-butyl)-oxiranyl]-8,11,17-trimethylene-oxacycloicosa-3,5,14-trien-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 18 steps 1.1: 90 percent / CSA / dimethylformamide / 38 °C 2.1: SO3*pyridine; i-Pr2NEt / dimethylsulfoxide / 1 h / 20 °C 3.1: NaHMDS / 0 - 20 °C 3.2: 4 h / 0 °C 4.1: CSA; H2O / methanol; CH2Cl2 / 7 h / 40 °C 5.1: imidazole; DMAP / dimethylformamide; CH2Cl2 / 12 h / 20 °C 6.1: 38 percent / CSA / 48 h / 40 °C 7.1: TBAF / tetrahydrofuran / 1.5 h 8.1: pyridine / CH2Cl2 / 0 - 20 °C 9.1: 98 percent / DMP; pyridine / CH2Cl2 10.1: t-BuLi; MgBr2*Et2O / benzene / 25 h / -78 - 20 °C 10.2: 70 percent / MgBr2*Et2O / CH2Cl2; benzene / 0.75 h / 0 °C 11.1: 81 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 88 percent / super-hydride / tetrahydrofuran / 0.58 h / 0 °C 13.1: 98 percent / DMP / pyridine / 1.5 h / 20 °C 14.1: MgBr2*Et2O / CH2Cl2; benzene 14.2: 60 percent / CH2Cl2; benzene; tetrahydrofuran / 1 h / 0 °C 15.1: 92 percent / NBS; AgNO3 / acetone / 20 °C 16.1: Bu3SnF; Red-Sil; TBAF / (PPh3)2PdCl2 / diethyl ether / 2.5 h / 20 °C 16.2: Cu(I) thiophenecarboxylate; NMP / 0.75 h / 0 - 20 °C 17.1: 35 percent / PhHC=Ru(PCy3)(IMes-H2)Cl2 / CH2Cl2 / 24 h / 40 °C 18.1: 92 percent / 2,6-lutidine / CH2Cl2 / 1.25 h / 0 °C
  • 59
  • (1S,2R)-1-(R)-1,4-Dioxa-spiro[4.5]dec-2-yl-2-methoxymethoxy-propane-1,3-diol [ No CAS ]
  • [ 488-82-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: CSA / 4 h / Ambient temperature 2: cc HCl / diethyl ether / 5 h / Ambient temperature
  • 60
  • [ 125676-45-1 ]
  • [ 488-82-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 30percent H2O2 / methanol; tetrahydrofuran; aq. KOH / 2.5 h / Ambient temperature 2: CSA / 4 h / Ambient temperature 3: cc HCl / diethyl ether / 5 h / Ambient temperature
  • 61
  • (R)-1-(R)-1,4-Dioxa-spiro[4.5]dec-2-yl-2-methoxymethoxy-prop-2-en-1-ol [ No CAS ]
  • [ 488-82-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: NH4Cl / Ambient temperature 2: 2=CH)Me2Si>2O>2> / toluene / 0.5 h / Ambient temperature 3: 30percent H2O2 / methanol; tetrahydrofuran; aq. KOH / 2.5 h / Ambient temperature 4: CSA / 4 h / Ambient temperature 5: cc HCl / diethyl ether / 5 h / Ambient temperature
  • 62
  • [ 126606-81-3 ]
  • [ 488-82-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 2=CH)Me2Si>2O>2> / toluene / 0.5 h / Ambient temperature 2: 30percent H2O2 / methanol; tetrahydrofuran; aq. KOH / 2.5 h / Ambient temperature 3: CSA / 4 h / Ambient temperature 4: cc HCl / diethyl ether / 5 h / Ambient temperature
  • 63
  • [ 87-72-9 ]
  • [ 87-72-9 ]
  • [ 50-99-7 ]
  • [ 59-23-4 ]
  • [ 488-82-4 ]
  • [ 87-99-0 ]
  • [ 50-70-4 ]
  • [ 608-66-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;ruthenium chloride supported on zirconia (3 wtpercent of ruthenium) and calcined at 500 C (ruthenium dispersion 40percent; chlorine content 50 ppm); In water; at 60℃; under 36778.6 Torr; for 100h;Product distribution / selectivity; EXAMPLE 6The procedure of example 4 was repeated except that the sugar containing 80 % xylose, 9 % arabinose, 5 % galactose, and 6 % glucose was used aes a reactant. After the reaction was conducted for 100 hours, the average purities of hydrogenated sugar alcohols were 79.8 %, 9.2 %, 5 %, and 5.9 % for xylitol, arabitol, galactitol, and sorbitol, respectively. Reactivity was not reduced even though the reaction was continuously performed for 1,000 hours or more.
  • 64
  • [ 2782-09-4 ]
  • [ 488-82-4 ]
YieldReaction ConditionsOperation in experiment
1 EXAMPLE 1 The pressure of hydrogen gas was adjusted to 8 MPa, an efficient mixer was turned on and the temperature was raised to 130° C. The reaction was interrupted after 8 h while the consumption of hydrogen gas was two-fold in comparison with the molar amount of the starting material. The yield of arabinitol was 90 mol-% of D-arabinono-1,4-lactone. The reaction solution was filtered and concentrated while D-arabinitol crystallized.
In water 2 EXAMPLE 2 EXAMPLE 2 D-glucose was oxidized in the same manner as in example 1. To a pressure reactor were added 20 mmol (3 g) D-arabinono-1,4-lactone, 3 g of a Raney-nickel catalyst and 20 ml water. The pressure of hydrogen gas was adjusted to 8 MPa, an efficient mixer was turned on and the temperature was raised to 130° C. The reaction was interrupted after 5 h. The yield of D-arabinitol was 37% and no other reaction products were present.
  • 65
  • [ 14694-95-2 ]
  • [ 6347-01-9 ]
  • [ 530-26-7 ]
  • [ 488-82-4 ]
  • [ 96-26-4 ]
  • [ 56-81-5 ]
  • [ 1198-69-2 ]
YieldReaction ConditionsOperation in experiment
With 2,2,6,6-tetramethylpiperine In further solvent(s) argon-filled glovebox, bibenzyl, 130°C, 28h, further products; product detd. by GC;
  • 66
  • [ 488-82-4 ]
  • [ 100-52-7 ]
  • [ 70831-50-4 ]
YieldReaction ConditionsOperation in experiment
62.4% Stage #1: D-Arabitol; benzaldehyde With hydrogenchloride Stage #2: With ammonia In water; toluene for 1h; 1 D-arabitol (300 g, 1.97 mol) and benzaldehyde (261 g, 2.46 mol) were mixed, hydrogen chloride gas was bubbled into them for 50 minutes, then the mixture was stirred under an argon stream. The mixture was allowed to stand overnight, then the solid crystalline mass obtained was broken up, a 5% aqueous ammonia solution (900 ml) and toluene (600 ml) were added, and the mixture was stirred for 1 hour. The crystal obtained was obtained by filtration, then successively washed with cooled water (600 ml) and toluene (600 mlx2) and dried in vacuo to obtain the above-identified compound 295 g (yield 62.4%). mp 130-131°C; 1H-NMR (CD3OD) δ: 7.51-7.30 (m, 5H), 5.58 (s, 1H), 4.18 (d, 1H, J=12Hz), 4.11 (d, 1H, J=12Hz), 3.87-3.28 (m, 5H); HRMS-FAB (m/z): calcd for C12H17O5 [M+H]+, 241.1076; found 241.1086.
  • 67
  • [ 1360168-38-2 ]
  • [ 124-41-4 ]
  • [ 488-82-4 ]
  • [ 112-63-0 ]
YieldReaction ConditionsOperation in experiment
1: 39 mg 2: 88 mg In methanol at 20℃; for 2h; 3.4. Hydrolysis of compound 3 Compound 3 (132 mg, 0.32 mmol) was dissolved in 1 ml of methanol and 28% sodium methoxide (260 μl, 1.28 mmol) was added. The mixture was stirred at room temperature for 2 h. The solvent was evaporated under reduced pressure to give white solid. The white solid was separated by silica gel column chromatography with a CH2Cl2/MeOH (9:1) repeatedly, to give d-arabinitol (39 mg, 0.26 mmol) and methyl linoleate (88 mg, 0.30 mmol). d-Arabinitol was identified by comparing with NMR data and specific rotation, while methyl linoleate was identified by comparing with MS spectrum and retention index (RI).
  • 68
  • [ 488-82-4 ]
  • [ 100-52-7 ]
  • (1R)-1-((5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl)ethane-1,2-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With hydrogenchloride In water for 72h; Inert atmosphere; 4.1.1 (1R)-1-((4R,5R)-5-Hydroxy-2-phenyl-1,3-dioxan-4-yl)ethane-1,2-diol (4)+(1R)-1-((4S,5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl)ethane-1,2-diol (5) The benzylidene protection was modified from literature procedure.46 In a dry round-bottomed flask containing benzaldehyde (8.5 mL, 84.45 mmol), HCl (0.59 mL (12 N), 7.1 mmol) was added and stirred. This was followed by the immediate addition of d-(+)-arabitol (10.71 g, 70.38 mmol) in spatula batches. The mixture was stirred briefly and left to stand for 3 days under argon. The resulting white solid was scraped out of the flask and quenched with dilute KOH (10%, 20 mL). The remaining solid particles were further crushed in the KOH mixture, filtered, and washed with distilled H2O. After drying, the mixture was obtained as a white solid (12.38 g, 73%).
  • 69
  • [ 50-99-7 ]
  • [ 488-82-4 ]
  • [ 526-95-4 ]
  • [ 87-73-0 ]
YieldReaction ConditionsOperation in experiment
With oxygen In water; acetonitrile at 30℃; for 0.166667h; UV-irradiation; liquid-phase photocatalytic selective oxidation of glucose The reaction system was stirred magnetically at 700 rpm to get a uniform suspension of the catalyst in the solution. A medium pressure 125 W mercury lamp (λmax = 365 nm) supplied by Photochemical Reactors Ltd. (Model RQ 3010) was placed inside the quartz immersion well as light irradiation source. The reaction temperature was established at 30 °C. Glucose solutions (2.8 mM) were prepared in a mixture of Milli-Q water and acetonitrile (ACN) (10:90, v/v) unless otherwise specified. Experiments were carried out from 150 mL of mother solution and a concentration of 1 g/L of the catalyst was used. All reactions were carried out under ambient air (no oxygen bubbling conditions). Approx. 2 mL of samples were taken from the photoreactor at pre-specified periods of time and were filtrated (0.20 μm, 25 mm φ nylon filters) in order to remove TiO2-supported particles before HPLC analyses.
  • 70
  • [ 488-82-4 ]
  • [ 501-97-3 ]
  • arabitol-1,5-diyl bis(3-(4-hydroxyphenyl)propionate) [ No CAS ]
  • 1-arabityl-3-(4-hydroxyphenyl)propionate [ No CAS ]
  • 5-arabityl-3-(4-hydroxyphenyl)propionate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With lipase B from Candida antarctica In dimethyl sulfoxide; <i>tert</i>-butyl alcohol at 60℃; for 72h; Molecular sieve; Enzymatic reaction; 7 Enzymatic esterification of sugar alcohols General procedure: HPPA and different sugar alcohols (xylitol, arabitol, mannitol, and sorbitol) were used as substrates for optimization of the reaction conditions, with regard to sugar alcohol esters synthesis. A sugar alcohol, at different initial concentrations (0.05-0.15 mol/L), and 3-(4-hydroxyphenyl)propionic acid, at different alcohol/acid molar ratios (between 5 and 0.3), were added to 1 mL binary mixtures of tert-butanol and dimethylsulfoxide (at 100:0, 95:5, 90:10, or 80:20% volume ratio, respectively), in 4 mL glass reaction flasks. Immobilized lipase from C. antarctica B (Novozyme 435) has been used as catalyst. The activity of Novozyme 435 for this type of aromatic substrate was previously assayed as 25 U/g, in the transesterification reaction of methyl-3-(4-hydroxyphenyl)-propionate with 1-octanol, in tert-butanol reaction medium, at 40 ◦C [30]. Molecular sieves (4A˚ , 0-0.1 g), and Novozyme 435 (0.01-0.05 g) were subsequently added. The reactions were performed in an incubator (ILW 115 STD; Pol-Eko-Aparatura, Poland) equipped with an orbital shaker(MIR-S100; Sanyo, Japan) at 250 rpm, at different temperatures (40, 50, 60, 70 ◦C)and for different time periods (12, 24, 48, 72 h). The progress of the esterification reaction was monitored by HPLC. All experiments were performed in duplicate, and the sampling was also done in duplicate. Results are given as the mean value of the four measurements. The conversions were calculated based on the consumption of the phenolic acid, while monoester and diester yields were calculated based on calibration curves of the pure compounds, isolated and purified in our laboratory.Identification of the products has been accomplished by MALDI-TOF MS (matrix assisted laser desorption-ionization time of flight mass spectrometry), based on the similarity between the m/z values identified in the spectra and the calculated values of the appropriate mono-, di-, and triesters 2.7.7 1-Arabityl-3-(4-hydroxyphenyl)propionate and 5-arabityl-3-(4-hydroxyphenyl)propionate (7) FTIR (cm-1): 3308 (ν(O-H)), 2935 (ν(C-H)), 1715 (ν(C=O) ester); 1H NMR (400 MHz, DMSO-d6, δ): 9.13 (br s, 2 * 1H, H-1' + H-1"), 7.01 + 7.00 (2 * d, 2 * 2H, J = 8.5 Hz, H-3' + H-3"), 6.66 (d, 2 * 2H, J = 8.5 Hz, H-2' + H-2"), 4.9-3.2 (multiple couplings, 2 * 11H, H-1 + H-2 + H-3 + H-4 + H-5 + H-1a + H-2a + H-3a + H-4a + H-5a + OH of carbohydrate moiety [4.81, d, 1H; 4.55, d, 1H; 4.5-4.4, m, 3H; 4.33, t, 1H; 4.28-4.25, m, 2H; 4.21, d, 1H; 4.02-3.88, m, 4H; 3.69, m, 2H; 3.59, m, 1H; 3.47, m, 1H; 3.42-3.28, m, 4H; 3.26, t, 1H]), 2.75 + 2.74 (2 * t, 2 * 2H, J = 7.8 Hz, H-5' + H-5"), 2.55 + 2.54 (2 * t, 2 * 2H, J = 7.8 Hz, H-6' + H6"); 13C NMR (100 MHz, DMSO-d6, δ) and proton-decoupled DEPT-135 (negative signals due to CH2, positive signals due to CH and CH3, CDCl3, δ): 172.49 + 172.30 (C-7' + C-7", C=O), 155.55 + 155.54 (C-1' + C-1"), 130.71 + 130.62 (C-4' + C-4"), 129.08 (C-3' + C-3"), 115.10 (C-2' + C-2"), 71.05 + 70.68 + 70.33 + 69.76 + 68.47 + 67.34 (C-2 + C-3 + C-4 + C-2a + C-3a + C-4a), 66.88 + 65.87 + 63.56 + 62.79 (C-1 + C-5 + C-1a + C-5a), 35.67 + 35.61 (C-6' + C-6"), 29.48 (C-5' + C-5"). 2.7.8 Arabitol-1,5-diyl bis(3-(4-hydroxyphenyl)propionate) (8) FTIR (cm-1): 3371 (ν(O-H)), 2945 (ν(C-H)), 1714 (ν(C=O) ester); 1H NMR (400 MHz, DMSO-d6, δ): 9.14 (br s, 2H, H-1' + H-1"), 7.00 + 6.99 (2 * d, 4H, J = 8.5 Hz, H-3' + H-3"), 6.65 (d, 4H, J = 8.5 Hz, H-2' + 2"), 4.9-3.2 (multiple couplings, 10H, H-1 + H-2 + H-3 + H-4 + H-5 + OH of carbohydrate moiety [4.87, d, 1H; 4.62, t, 2H; 4.26, dd, 1H; 4.03-3.90, m, 4H; 3.70, m, 1H; 3.28, t, 1H]), 2.75 + 2.74 (2 * t, 4H, J = 7.5 Hz, H-5' + H-5"), 2.55 + 2.54 (2 * t, 4H, J = 7.5 Hz, H-6' + H-6"); 13C NMR (100 MHz, DMSO-d6, δ) and proton-decoupled DEPT-135 (negative signals due to CH2, positive signals due to CH and CH3, CDCl3, δ): 172.44 + 172.26 (C-7' + C-7", C=O), 155.54 + 155.52 (C-1' + C-1"), 130.67 + 130.58 (C-4' + C-4"), 129.04 (C-3' + C-3"), 115.07 + 115.02 (C-2' + C-2"), 70.54 + 68.12 + 66.93 (C-2 + C-3 + C-4), 66.69 + 65.72 (C-1 + C-5), 35.64 + 35.59 (C-6' + C-6"), 29.45 (C-5' + C-5").
  • 71
  • [ 488-82-4 ]
  • [ 10323-20-3 ]
YieldReaction ConditionsOperation in experiment
With Yarrowia lipolytica short chain dehydrogenase/reductase; nicotinamide adenine dinucleotide phosphate; magnesium chloride In aq. buffer at 28℃; for 0.166667h; Enzymatic reaction; General procedure: Unless otherwise stated, purified tagged YlSDR (1-10μM) was assayed in 50mM Tris-HCl containing 2mM MgCl2, pH 8.0, 10mM substrate (for lipophilic substrates, additional 0.15% Tween 20) and 1mM NADP+ or NAD+. The increase of absorbance at 340nm was monitored at 28°C for 10min (or 12h for ribose). For NAD+, no activity was observed under these conditions. The reported values represent the average of at least four measurements with appropriate blanks substracted. One activity unit is defined as the amount of enzyme catalyzing the reduction of 1μM of NADP+ per minute. Kinetic parameters for oxidation were determined at pH 10.0 from unweighted non-linear least-square fits of experimental data using the program Sigmaplot (version 12.3).
  • 72
  • [ 58-86-6 ]
  • [ 488-82-4 ]
  • [ 87-99-0 ]
YieldReaction ConditionsOperation in experiment
6%; 50% With hydrogen; In water; at 60℃; under 12001.2 Torr; for 4h;Green chemistry;Catalytic behavior; General procedure: Glucose and xylose hydrogenation reactions were carried out in a batch reactor (Amar equipments, India). The reactor was charged with 0.83 mmol of glucose or 1.00 mmol of xylose in 35 mL water. During reactions catalyst/substrate ratio was kept constant at 1:2 (wt/wt). When reactions were conducted using HT, 0.075 g of HT was added. Experiments were conducted at temperatures ranging between 60 C and 190 C under 8-24 bar of hydrogen pressure.The reactions were conducted for 2-6 h. Reaction mixture was analyzed using HPLC (Agilent, USA) equipped with HC-75 Pb++(9 m,7.8 mm × 300 mm) column. Water was used as an eluent, at the flow rate of 0.6 mL/min, and RID (model no. 1260 infinity) was used to detect the compounds. The products which are poorly separable by using HC-75 Pb++column, were analyzed using HPLC (Shimadzu,Japan) equipped with HC-75 H+(9 m, 7.8 mm × 305 mm) column. Succinic acid (0.5 mmol) is used as an eluent (0.5 mL/min). The refractive index detector (Model no. RID-6A) was used for the detection and calibration of compounds. The calibration of all the compounds was done using commercially available standards.
With hydrogen; In water; at 120℃; under 41254.1 Torr; for 1h;Autoclave; Inert atmosphere; Green chemistry;Catalytic behavior; The xylose hydrogenation experiments catalyzed by Ru/HYZwere carried out batch wise in 300 mL of three phase slurry reactorin the temperature range from 100 to 140 C at hydrogen pressure(2.0-5.5 MPa) by various stirring rate (400-1200 rpm). In typical hydrogenation experiment, required amount of catalyst (Ru/HYZ)and 100 mL of xylose solution were charged into stainless steel autoclave reactor. The reactor was fitted air tight and flushed with nitrogen gas three times at room temperature. Then, reactor was brought to desired temperature and pressurized with hydrogen which was considered as the zero reaction time. Hydrogenation reaction was initiated by stirring the entire reaction mass. Constant hydrogen pressure was maintained by supplying hydrogen gas manually through gas inlet valve during the reaction. During hydrogenation at different time intervals, the product components were analyzed using a HPLC (Younglin Instrument, Acme 9000)equipped with refractive index (RI) detector and Sugar-Pak column.De-ionized water was used as an eluent for the analysis at a flowrate of 0.4 mL/min at 70 C. After a stipulated period, the stirring was stopped and the reactor was abruptly cooled down, depressurized,flushed with N2, opened and decanted the reaction mixture from the catalyst to collect sample for final analysis. Xylose (XLS) conversion, selectivity to main xylitol (XTL) and arabitol (ARB) are calculated using following expressions. XLSConv. (%)=(1- mole of xylose at particular time/initial mole of xylose)×100 XTLSelc. (%)=(mole of XTL/mole of all products formed)×100 ARBSelc. (%)=(mole of ARB/mole of all products formed)×100
  • 73
  • [ 10323-20-3 ]
  • [ 57-55-6 ]
  • [ 488-82-4 ]
  • [ 107-21-1 ]
  • [ 56-81-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In water at 244.84℃; for 3h;
  • 74
  • [ 9004-34-6 ]
  • [ 2418-52-2 ]
  • [ 909878-64-4 ]
  • [ 488-82-4 ]
  • [ 87-99-0 ]
  • [ 69-65-8 ]
  • [ 50-70-4 ]
YieldReaction ConditionsOperation in experiment
With water; hydrogen at 210℃; for 0.5h; Autoclave; Cellulose reaction General procedure: Cellulose (microcrystalline, Alfa Aesar) reactions were carried out in a stainless steel autoclave (100mL) typically at 210°C and 6MPa H2 for 30min with vigorous stirring at a speed of 800rpm. In a typical run, 1g cellulose and 0.4g catalyst were introduced into the autoclave containing 50mL H2O. Afterwards, the reactor was fully purged with H2 (>99.999%, Beijing Longhui Jingcheng), pressurized with H2 to 6.0MPa and then heated to 210°C which was kept constant during the reaction. After cooling to room temperature in water, the reaction mixture was filtrated and the solids were washed several times with deionized water. The solids including the catalyst and remaining cellulose were washed with acetone three times and then fully dried in an oven at 60°C for 24h. Cellulose conversions were determined by the change in the weight of cellulose loaded before and after the reactions. The products in the liquid phase (e.g. polyols) were analyzed by high-performance liquid chromatography (Shimadzu LC-20A) using Bio-Rad Aminex HPX-87H with a RID detector. The product selectivities were reported on a carbon basis.
  • 75
  • [ 9004-34-6 ]
  • [ 57-55-6 ]
  • [ 2418-52-2 ]
  • [ 909878-64-4 ]
  • [ 488-82-4 ]
  • [ 87-99-0 ]
  • [ 69-65-8 ]
  • [ 50-70-4 ]
  • [ 107-21-1 ]
  • [ 116-09-6 ]
  • [ 56-81-5 ]
YieldReaction ConditionsOperation in experiment
With water; hydrogen at 210℃; for 0.5h; Autoclave; Cellulose reaction General procedure: Cellulose (microcrystalline, Alfa Aesar) reactions were carried out in a stainless steel autoclave (100mL) typically at 210°C and 6MPa H2 for 30min with vigorous stirring at a speed of 800rpm. In a typical run, 1g cellulose and 0.4g catalyst were introduced into the autoclave containing 50mL H2O. Afterwards, the reactor was fully purged with H2 (>99.999%, Beijing Longhui Jingcheng), pressurized with H2 to 6.0MPa and then heated to 210°C which was kept constant during the reaction. After cooling to room temperature in water, the reaction mixture was filtrated and the solids were washed several times with deionized water. The solids including the catalyst and remaining cellulose were washed with acetone three times and then fully dried in an oven at 60°C for 24h. Cellulose conversions were determined by the change in the weight of cellulose loaded before and after the reactions. The products in the liquid phase (e.g. polyols) were analyzed by high-performance liquid chromatography (Shimadzu LC-20A) using Bio-Rad Aminex HPX-87H with a RID detector. The product selectivities were reported on a carbon basis.
  • 76
  • [ 9004-34-6 ]
  • [ 57-55-6 ]
  • [ 2418-52-2 ]
  • [ 909878-64-4 ]
  • [ 488-82-4 ]
  • [ 87-99-0 ]
  • [ 69-65-8 ]
  • [ 50-70-4 ]
  • [ 56-81-5 ]
YieldReaction ConditionsOperation in experiment
With water; hydrogen at 210℃; for 0.5h; Autoclave; Cellulose reaction General procedure: Cellulose (microcrystalline, Alfa Aesar) reactions were carried out in a stainless steel autoclave (100mL) typically at 210°C and 6MPa H2 for 30min with vigorous stirring at a speed of 800rpm. In a typical run, 1g cellulose and 0.4g catalyst were introduced into the autoclave containing 50mL H2O. Afterwards, the reactor was fully purged with H2 (>99.999%, Beijing Longhui Jingcheng), pressurized with H2 to 6.0MPa and then heated to 210°C which was kept constant during the reaction. After cooling to room temperature in water, the reaction mixture was filtrated and the solids were washed several times with deionized water. The solids including the catalyst and remaining cellulose were washed with acetone three times and then fully dried in an oven at 60°C for 24h. Cellulose conversions were determined by the change in the weight of cellulose loaded before and after the reactions. The products in the liquid phase (e.g. polyols) were analyzed by high-performance liquid chromatography (Shimadzu LC-20A) using Bio-Rad Aminex HPX-87H with a RID detector. The product selectivities were reported on a carbon basis.
  • 77
  • [ 9004-34-6 ]
  • [ 57-55-6 ]
  • [ 2418-52-2 ]
  • [ 909878-64-4 ]
  • [ 79-33-4 ]
  • [ 488-82-4 ]
  • [ 87-99-0 ]
  • [ 69-65-8 ]
  • [ 50-70-4 ]
  • [ 107-21-1 ]
  • [ 56-81-5 ]
YieldReaction ConditionsOperation in experiment
With water; hydrogen at 210℃; for 1h; Cellulose reaction General procedure: Cellulose (microcrystalline, Alfa Aesar) reactions were carried out in a stainless steel autoclave (100mL) typically at 210°C and 6MPa H2 for 30min with vigorous stirring at a speed of 800rpm. In a typical run, 1g cellulose and 0.4g catalyst were introduced into the autoclave containing 50mL H2O. Afterwards, the reactor was fully purged with H2 (>99.999%, Beijing Longhui Jingcheng), pressurized with H2 to 6.0MPa and then heated to 210°C which was kept constant during the reaction. After cooling to room temperature in water, the reaction mixture was filtrated and the solids were washed several times with deionized water. The solids including the catalyst and remaining cellulose were washed with acetone three times and then fully dried in an oven at 60°C for 24h. Cellulose conversions were determined by the change in the weight of cellulose loaded before and after the reactions. The products in the liquid phase (e.g. polyols) were analyzed by high-performance liquid chromatography (Shimadzu LC-20A) using Bio-Rad Aminex HPX-87H with a RID detector. The product selectivities were reported on a carbon basis.
  • 78
  • [ 9004-34-6 ]
  • [ 57-55-6 ]
  • [ 2418-52-2 ]
  • [ 909878-64-4 ]
  • [ 488-82-4 ]
  • [ 87-99-0 ]
  • [ 69-65-8 ]
  • [ 50-70-4 ]
  • [ 107-21-1 ]
  • [ 56-81-5 ]
YieldReaction ConditionsOperation in experiment
With water; hydrogen at 210℃; for 1h; Cellulose reaction General procedure: Cellulose (microcrystalline, Alfa Aesar) reactions were carried out in a stainless steel autoclave (100mL) typically at 210°C and 6MPa H2 for 30min with vigorous stirring at a speed of 800rpm. In a typical run, 1g cellulose and 0.4g catalyst were introduced into the autoclave containing 50mL H2O. Afterwards, the reactor was fully purged with H2 (>99.999%, Beijing Longhui Jingcheng), pressurized with H2 to 6.0MPa and then heated to 210°C which was kept constant during the reaction. After cooling to room temperature in water, the reaction mixture was filtrated and the solids were washed several times with deionized water. The solids including the catalyst and remaining cellulose were washed with acetone three times and then fully dried in an oven at 60°C for 24h. Cellulose conversions were determined by the change in the weight of cellulose loaded before and after the reactions. The products in the liquid phase (e.g. polyols) were analyzed by high-performance liquid chromatography (Shimadzu LC-20A) using Bio-Rad Aminex HPX-87H with a RID detector. The product selectivities were reported on a carbon basis.
  • 79
  • [ 9004-34-6 ]
  • [ 57-55-6 ]
  • [ 2418-52-2 ]
  • [ 909878-64-4 ]
  • [ 488-82-4 ]
  • [ 87-99-0 ]
  • [ 69-65-8 ]
  • [ 50-70-4 ]
  • [ 107-21-1 ]
  • [ 116-09-6 ]
YieldReaction ConditionsOperation in experiment
With water; hydrogen at 210℃; for 1h; Cellulose reaction General procedure: Cellulose (microcrystalline, Alfa Aesar) reactions were carried out in a stainless steel autoclave (100mL) typically at 210°C and 6MPa H2 for 30min with vigorous stirring at a speed of 800rpm. In a typical run, 1g cellulose and 0.4g catalyst were introduced into the autoclave containing 50mL H2O. Afterwards, the reactor was fully purged with H2 (>99.999%, Beijing Longhui Jingcheng), pressurized with H2 to 6.0MPa and then heated to 210°C which was kept constant during the reaction. After cooling to room temperature in water, the reaction mixture was filtrated and the solids were washed several times with deionized water. The solids including the catalyst and remaining cellulose were washed with acetone three times and then fully dried in an oven at 60°C for 24h. Cellulose conversions were determined by the change in the weight of cellulose loaded before and after the reactions. The products in the liquid phase (e.g. polyols) were analyzed by high-performance liquid chromatography (Shimadzu LC-20A) using Bio-Rad Aminex HPX-87H with a RID detector. The product selectivities were reported on a carbon basis.
  • 80
  • [ 9004-34-6 ]
  • [ 2418-52-2 ]
  • [ 909878-64-4 ]
  • [ 488-82-4 ]
  • [ 87-99-0 ]
  • [ 116-09-6 ]
YieldReaction ConditionsOperation in experiment
With water; hydrogen at 210℃; for 0.5h; Autoclave; Cellulose reaction General procedure: Cellulose (microcrystalline, Alfa Aesar) reactions were carried out in a stainless steel autoclave (100mL) typically at 210°C and 6MPa H2 for 30min with vigorous stirring at a speed of 800rpm. In a typical run, 1g cellulose and 0.4g catalyst were introduced into the autoclave containing 50mL H2O. Afterwards, the reactor was fully purged with H2 (>99.999%, Beijing Longhui Jingcheng), pressurized with H2 to 6.0MPa and then heated to 210°C which was kept constant during the reaction. After cooling to room temperature in water, the reaction mixture was filtrated and the solids were washed several times with deionized water. The solids including the catalyst and remaining cellulose were washed with acetone three times and then fully dried in an oven at 60°C for 24h. Cellulose conversions were determined by the change in the weight of cellulose loaded before and after the reactions. The products in the liquid phase (e.g. polyols) were analyzed by high-performance liquid chromatography (Shimadzu LC-20A) using Bio-Rad Aminex HPX-87H with a RID detector. The product selectivities were reported on a carbon basis.
  • 81
  • [ 9004-34-6 ]
  • [ 2418-52-2 ]
  • [ 909878-64-4 ]
  • [ 79-33-4 ]
  • [ 488-82-4 ]
  • [ 87-99-0 ]
  • [ 50-99-7 ]
  • [ 116-09-6 ]
YieldReaction ConditionsOperation in experiment
With water; hydrogen at 210℃; for 0.5h; Autoclave; Cellulose reaction General procedure: Cellulose (microcrystalline, Alfa Aesar) reactions were carried out in a stainless steel autoclave (100mL) typically at 210°C and 6MPa H2 for 30min with vigorous stirring at a speed of 800rpm. In a typical run, 1g cellulose and 0.4g catalyst were introduced into the autoclave containing 50mL H2O. Afterwards, the reactor was fully purged with H2 (>99.999%, Beijing Longhui Jingcheng), pressurized with H2 to 6.0MPa and then heated to 210°C which was kept constant during the reaction. After cooling to room temperature in water, the reaction mixture was filtrated and the solids were washed several times with deionized water. The solids including the catalyst and remaining cellulose were washed with acetone three times and then fully dried in an oven at 60°C for 24h. Cellulose conversions were determined by the change in the weight of cellulose loaded before and after the reactions. The products in the liquid phase (e.g. polyols) were analyzed by high-performance liquid chromatography (Shimadzu LC-20A) using Bio-Rad Aminex HPX-87H with a RID detector. The product selectivities were reported on a carbon basis.
  • 82
  • [ 9004-34-6 ]
  • [ 2418-52-2 ]
  • [ 909878-64-4 ]
  • [ 79-33-4 ]
  • [ 488-82-4 ]
  • [ 87-99-0 ]
  • [ 116-09-6 ]
YieldReaction ConditionsOperation in experiment
With water; hydrogen at 210℃; for 0.5h; Autoclave; Cellulose reaction General procedure: Cellulose (microcrystalline, Alfa Aesar) reactions were carried out in a stainless steel autoclave (100mL) typically at 210°C and 6MPa H2 for 30min with vigorous stirring at a speed of 800rpm. In a typical run, 1g cellulose and 0.4g catalyst were introduced into the autoclave containing 50mL H2O. Afterwards, the reactor was fully purged with H2 (>99.999%, Beijing Longhui Jingcheng), pressurized with H2 to 6.0MPa and then heated to 210°C which was kept constant during the reaction. After cooling to room temperature in water, the reaction mixture was filtrated and the solids were washed several times with deionized water. The solids including the catalyst and remaining cellulose were washed with acetone three times and then fully dried in an oven at 60°C for 24h. Cellulose conversions were determined by the change in the weight of cellulose loaded before and after the reactions. The products in the liquid phase (e.g. polyols) were analyzed by high-performance liquid chromatography (Shimadzu LC-20A) using Bio-Rad Aminex HPX-87H with a RID detector. The product selectivities were reported on a carbon basis.
  • 83
  • [ 87-99-0 ]
  • [ 488-82-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogen; at 199.84℃; under 30003 Torr; for 3h;Autoclave; General procedure: Xylitol hydrogenolysis reactions were carried out in a stainlesssteel autoclave (100 ml) at a stirring speed of 800 rpm. Typically,40 g of 10 wt% xylitol (99%, Alfa Aesar) aqueous solution, properamount of Ni catalysts (varied depending on xylitol conversion)and also for the Ni/C case, solid base were introduced to the auto-clave. Afterwards, the reactor was purged with H2(>99.99%, BeijingHuayuan) three times, and pressurized with H2to 4.0 MPa andheated to 473 K, which was kept constant during the reaction.The reactant and liquid products, after silylation with hexame-thyldisilazane (HDMS) and trimethylchlorosilane (TMSCl) (both?98.0%, Sinopharm Chemical) in pyridine (AR, Shantou XilongChemical), were analyzed by gas chromatography (Agilent 7890A)using a capillary column HP-1ms (30 m × 0.25 mm × 0.25 m) anda flame ionization detector. The detected liquid products includedethylene glycol, propylene glycol, glycerol, lactic acid, threitol,arabitol, and dehydroxy-pentitols (mainly 1,2,5-pentanetriol and1,2,4,5-pentanetetraol), and dehydrated product hydroxyl furan.Gas products, i.e. CH4and CO2, were also detected in trace amounts,and thus not discussed in this work. Xylitol conversion and productselectivity are reported on a carbon basis, and xylitol reaction activ-ity is reported as molar xylitol conversion rate per mole of metalloaded per hour (h-1).
  • 84
  • [ 87-99-0 ]
  • [ 57-55-6 ]
  • [ 14697-46-2 ]
  • [ 89617-06-1 ]
  • [ 488-82-4 ]
  • [ 107-21-1 ]
YieldReaction ConditionsOperation in experiment
With cerium(IV) oxide; hydrogen at 199.84℃; for 3h; Autoclave; General procedure: Xylitol hydrogenolysis reactions were carried out in a stainlesssteel autoclave (100 ml) at a stirring speed of 800 rpm. Typically,40 g of 10 wt% xylitol (99%, Alfa Aesar) aqueous solution, properamount of Ni catalysts (varied depending on xylitol conversion)and also for the Ni/C case, solid base were introduced to the auto-clave. Afterwards, the reactor was purged with H2(>99.99%, BeijingHuayuan) three times, and pressurized with H2to 4.0 MPa andheated to 473 K, which was kept constant during the reaction.The reactant and liquid products, after silylation with hexame-thyldisilazane (HDMS) and trimethylchlorosilane (TMSCl) (both≥98.0%, Sinopharm Chemical) in pyridine (AR, Shantou XilongChemical), were analyzed by gas chromatography (Agilent 7890A)using a capillary column HP-1ms (30 m × 0.25 mm × 0.25 m) anda flame ionization detector. The detected liquid products includedethylene glycol, propylene glycol, glycerol, lactic acid, threitol,arabitol, and dehydroxy-pentitols (mainly 1,2,5-pentanetriol and1,2,4,5-pentanetetraol), and dehydrated product hydroxyl furan.Gas products, i.e. CH4and CO2, were also detected in trace amounts,and thus not discussed in this work. Xylitol conversion and productselectivity are reported on a carbon basis, and xylitol reaction activ-ity is reported as molar xylitol conversion rate per mole of metalloaded per hour (h-1).
With hydrogen at 199.84℃; for 3h; Autoclave; General procedure: Xylitol hydrogenolysis reactions were carried out in a stainlesssteel autoclave (100 ml) at a stirring speed of 800 rpm. Typically,40 g of 10 wt% xylitol (99%, Alfa Aesar) aqueous solution, properamount of Ni catalysts (varied depending on xylitol conversion)and also for the Ni/C case, solid base were introduced to the auto-clave. Afterwards, the reactor was purged with H2(>99.99%, BeijingHuayuan) three times, and pressurized with H2to 4.0 MPa andheated to 473 K, which was kept constant during the reaction.The reactant and liquid products, after silylation with hexame-thyldisilazane (HDMS) and trimethylchlorosilane (TMSCl) (both≥98.0%, Sinopharm Chemical) in pyridine (AR, Shantou XilongChemical), were analyzed by gas chromatography (Agilent 7890A)using a capillary column HP-1ms (30 m × 0.25 mm × 0.25 m) anda flame ionization detector. The detected liquid products includedethylene glycol, propylene glycol, glycerol, lactic acid, threitol,arabitol, and dehydroxy-pentitols (mainly 1,2,5-pentanetriol and1,2,4,5-pentanetetraol), and dehydrated product hydroxyl furan.Gas products, i.e. CH4and CO2, were also detected in trace amounts,and thus not discussed in this work. Xylitol conversion and productselectivity are reported on a carbon basis, and xylitol reaction activ-ity is reported as molar xylitol conversion rate per mole of metalloaded per hour (h-1).
  • 85
  • [ 87-99-0 ]
  • [ 57-55-6 ]
  • [ 14697-46-2 ]
  • [ 89617-06-1 ]
  • [ 488-82-4 ]
  • [ 107-21-1 ]
  • [ 56-81-5 ]
YieldReaction ConditionsOperation in experiment
With aluminum oxide; hydrogen; at 199.84℃; under 30003 Torr; for 3h;Autoclave; General procedure: Xylitol hydrogenolysis reactions were carried out in a stainlesssteel autoclave (100 ml) at a stirring speed of 800 rpm. Typically,40 g of 10 wt% xylitol (99%, Alfa Aesar) aqueous solution, properamount of Ni catalysts (varied depending on xylitol conversion)and also for the Ni/C case, solid base were introduced to the auto-clave. Afterwards, the reactor was purged with H2(>99.99%, BeijingHuayuan) three times, and pressurized with H2to 4.0 MPa andheated to 473 K, which was kept constant during the reaction.The reactant and liquid products, after silylation with hexame-thyldisilazane (HDMS) and trimethylchlorosilane (TMSCl) (both?98.0%, Sinopharm Chemical) in pyridine (AR, Shantou XilongChemical), were analyzed by gas chromatography (Agilent 7890A)using a capillary column HP-1ms (30 m × 0.25 mm × 0.25 m) anda flame ionization detector. The detected liquid products includedethylene glycol, propylene glycol, glycerol, lactic acid, threitol,arabitol, and dehydroxy-pentitols (mainly 1,2,5-pentanetriol and1,2,4,5-pentanetetraol), and dehydrated product hydroxyl furan.Gas products, i.e. CH4and CO2, were also detected in trace amounts,and thus not discussed in this work. Xylitol conversion and productselectivity are reported on a carbon basis, and xylitol reaction activ-ity is reported as molar xylitol conversion rate per mole of metalloaded per hour (h-1).
With hydrogen; zirconium(IV) oxide; at 199.84℃; under 30003 Torr; for 3h;Autoclave; General procedure: Xylitol hydrogenolysis reactions were carried out in a stainlesssteel autoclave (100 ml) at a stirring speed of 800 rpm. Typically,40 g of 10 wt% xylitol (99%, Alfa Aesar) aqueous solution, properamount of Ni catalysts (varied depending on xylitol conversion)and also for the Ni/C case, solid base were introduced to the auto-clave. Afterwards, the reactor was purged with H2(>99.99%, BeijingHuayuan) three times, and pressurized with H2to 4.0 MPa andheated to 473 K, which was kept constant during the reaction.The reactant and liquid products, after silylation with hexame-thyldisilazane (HDMS) and trimethylchlorosilane (TMSCl) (both?98.0%, Sinopharm Chemical) in pyridine (AR, Shantou XilongChemical), were analyzed by gas chromatography (Agilent 7890A)using a capillary column HP-1ms (30 m × 0.25 mm × 0.25 m) anda flame ionization detector. The detected liquid products includedethylene glycol, propylene glycol, glycerol, lactic acid, threitol,arabitol, and dehydroxy-pentitols (mainly 1,2,5-pentanetriol and1,2,4,5-pentanetetraol), and dehydrated product hydroxyl furan.Gas products, i.e. CH4and CO2, were also detected in trace amounts,and thus not discussed in this work. Xylitol conversion and productselectivity are reported on a carbon basis, and xylitol reaction activ-ity is reported as molar xylitol conversion rate per mole of metalloaded per hour (h-1).
With hydrogen; calcium carbonate; at 199.84℃; under 30003 Torr; for 3h;Autoclave; General procedure: Xylitol hydrogenolysis reactions were carried out in a stainlesssteel autoclave (100 ml) at a stirring speed of 800 rpm. Typically,40 g of 10 wt% xylitol (99%, Alfa Aesar) aqueous solution, properamount of Ni catalysts (varied depending on xylitol conversion)and also for the Ni/C case, solid base were introduced to the auto-clave. Afterwards, the reactor was purged with H2(>99.99%, BeijingHuayuan) three times, and pressurized with H2to 4.0 MPa andheated to 473 K, which was kept constant during the reaction.The reactant and liquid products, after silylation with hexame-thyldisilazane (HDMS) and trimethylchlorosilane (TMSCl) (both?98.0%, Sinopharm Chemical) in pyridine (AR, Shantou XilongChemical), were analyzed by gas chromatography (Agilent 7890A)using a capillary column HP-1ms (30 m × 0.25 mm × 0.25 m) anda flame ionization detector. The detected liquid products includedethylene glycol, propylene glycol, glycerol, lactic acid, threitol,arabitol, and dehydroxy-pentitols (mainly 1,2,5-pentanetriol and1,2,4,5-pentanetetraol), and dehydrated product hydroxyl furan.Gas products, i.e. CH4and CO2, were also detected in trace amounts,and thus not discussed in this work. Xylitol conversion and productselectivity are reported on a carbon basis, and xylitol reaction activ-ity is reported as molar xylitol conversion rate per mole of metalloaded per hour (h-1).
With hydrogen; at 199.84℃; under 30003 Torr; for 3h;Autoclave; General procedure: Xylitol hydrogenolysis reactions were carried out in a stainlesssteel autoclave (100 ml) at a stirring speed of 800 rpm. Typically,40 g of 10 wt% xylitol (99%, Alfa Aesar) aqueous solution, properamount of Ni catalysts (varied depending on xylitol conversion)and also for the Ni/C case, solid base were introduced to the auto-clave. Afterwards, the reactor was purged with H2(>99.99%, BeijingHuayuan) three times, and pressurized with H2to 4.0 MPa andheated to 473 K, which was kept constant during the reaction.The reactant and liquid products, after silylation with hexame-thyldisilazane (HDMS) and trimethylchlorosilane (TMSCl) (both?98.0%, Sinopharm Chemical) in pyridine (AR, Shantou XilongChemical), were analyzed by gas chromatography (Agilent 7890A)using a capillary column HP-1ms (30 m × 0.25 mm × 0.25 m) anda flame ionization detector. The detected liquid products includedethylene glycol, propylene glycol, glycerol, lactic acid, threitol,arabitol, and dehydroxy-pentitols (mainly 1,2,5-pentanetriol and1,2,4,5-pentanetetraol), and dehydrated product hydroxyl furan.Gas products, i.e. CH4and CO2, were also detected in trace amounts,and thus not discussed in this work. Xylitol conversion and productselectivity are reported on a carbon basis, and xylitol reaction activ-ity is reported as molar xylitol conversion rate per mole of metalloaded per hour (h-1).

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