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[ CAS No. 149-32-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 149-32-6
Chemical Structure| 149-32-6
Chemical Structure| 149-32-6
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Product Details of [ 149-32-6 ]

CAS No. :149-32-6 MDL No. :MFCD00004710
Formula : C4H10O4 Boiling Point : -
Linear Structure Formula :HOCH2CH(OH)CH(OH)CH2OH InChI Key :UNXHWFMMPAWVPI-ZXZARUISSA-N
M.W : 122.12 Pubchem ID :222285
Synonyms :
Erythritol
Chemical Name :(2R,3S)-rel-Butane-1,2,3,4-tetraol

Calculated chemistry of [ 149-32-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 4.0
Molar Refractivity : 25.99
TPSA : 80.92 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.94
Log Po/w (XLOGP3) : -2.29
Log Po/w (WLOGP) : -2.31
Log Po/w (MLOGP) : -1.91
Log Po/w (SILICOS-IT) : -1.27
Consensus Log Po/w : -1.37

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 3.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 1.04
Solubility : 1350.0 mg/ml ; 11.1 mol/l
Class : Highly soluble
Log S (Ali) : 1.13
Solubility : 1630.0 mg/ml ; 13.4 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 1.56
Solubility : 4430.0 mg/ml ; 36.3 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.42

Safety of [ 149-32-6 ]

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 [ 149-32-6 ]

* 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 [ 149-32-6 ]

[ 149-32-6 ] Synthesis Path-Downstream   1~94

  • 2
  • [ 149-32-6 ]
  • [ 7297-25-8 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid und folgendes Behandeln mit Salpeterschwefelsaeure unter Kuehlung;
  • 7
  • [ 3262-89-3 ]
  • [ 149-32-6 ]
  • [ 71166-92-2 ]
  • 8
  • [ 97-94-9 ]
  • [ 149-32-6 ]
  • [ 58163-66-9 ]
  • 9
  • [ 149-32-6 ]
  • [ 3724-43-4 ]
  • [ 100378-98-1 ]
  • 10
  • [ 149-32-6 ]
  • [ 533-50-6 ]
  • 11
  • [ 149-32-6 ]
  • [ 1009-93-4 ]
  • [ 42959-20-6 ]
  • 12
  • [ 110-87-2 ]
  • [ 109-65-9 ]
  • [ 149-32-6 ]
  • [ 84379-45-3 ]
  • [ 84379-46-4 ]
  • 13
  • [ 110-87-2 ]
  • [ 109-65-9 ]
  • [ 149-32-6 ]
  • [ 84379-47-5 ]
  • 14
  • [ 110-87-2 ]
  • [ 109-65-9 ]
  • [ 149-32-6 ]
  • [ 84379-49-7 ]
  • [ 84379-44-2 ]
  • C23H42O7 [ No CAS ]
  • 15
  • [ 109-65-9 ]
  • [ 149-32-6 ]
  • 1,3,4-Tributoxy-butan-2-ol [ No CAS ]
  • [ 84379-47-5 ]
  • 16
  • [ 50-00-0 ]
  • [ 3068-00-6 ]
  • [ 149-32-6 ]
  • [ 107-21-1 ]
  • [ 89615-91-8 ]
  • [ 56-81-5 ]
  • [ 50-70-4 ]
  • 17
  • [ 64-18-6 ]
  • [ 149-32-6 ]
  • [ 149815-82-7 ]
  • 18
  • [ 13096-62-3 ]
  • [ 149-32-6 ]
  • 1,2:3,4-di-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosylidene)erythritol [ No CAS ]
  • 19
  • [ 149-32-6 ]
  • [ 75194-94-4 ]
  • C36H74N4O12P4 [ No CAS ]
  • 20
  • [ 149-32-6 ]
  • [ 108-24-7 ]
  • [ 7208-40-4 ]
YieldReaction ConditionsOperation in experiment
99% With pyridine; dmap for 5h; Inert atmosphere;
34% With triethylamine In dichloromethane at 65℃; for 16h; 81 Example 81: (2R, 3S)-butane-1 ,2,3,4-tetrayl tetraacetate To a solution of (2R,3S)-butane-1 ,2,3,4-tetrol (0.5 g) and triethylamine (3.31 g) in CH2CI2 (20 mL) was added AC20 (3.34 g). Then the mixture was stirred at 65°C for 16 h. The solvent was removed underreduced pressure and the residue was purified by column chromatography (Si02, petroleum ether / ethylacetate, 0:1 to 20:1) to give (2R,3S)-butane-1 ,2,3,4-tetrayl tetraacetate (0.4 g, 34%) as a white solid. 1NMR (400 MHz, DMSO-d6): 05.178 - 5.134 (m, 2H), 4.257 (m, 2H), 4.165 (m, 2H), 2.029 (s, 6H),1 .995(s, 6H) ppm
With pyridine Yield given;
With pyridine
With pyridine; dmap In dichloromethane at 0℃; for 7h; Inert atmosphere;
With perchloric acid at 0 - 20℃; for 0.0833333h;
With sodium acetate at 90℃; for 2h;

  • 21
  • [ 149-32-6 ]
  • [ 98-09-9 ]
  • [ 219695-76-8 ]
  • 22
  • [ 149-32-6 ]
  • [ 70072-03-6 ]
  • C28H58N4O12P4 [ No CAS ]
  • 24
  • [ 149-32-6 ]
  • P2S5 [ No CAS ]
  • [ 188290-36-0 ]
  • 25
  • [ 149-32-6 ]
  • [ 10034-85-2 ]
  • [ 513-48-4 ]
  • 26
  • [ 149-32-6 ]
  • [ 10026-13-8 ]
  • [ 3405-32-1 ]
  • 27
  • [ 149-32-6 ]
  • bromine water [ No CAS ]
  • [ 40031-31-0 ]
  • 28
  • [ 149-32-6 ]
  • [ 7722-84-1 ]
  • ferro-compound [ No CAS ]
  • [ 40031-31-0 ]
  • 29
  • [ 149-32-6 ]
  • [ 7732-18-5 ]
  • platinum [ No CAS ]
  • [ 488-16-4 ]
YieldReaction ConditionsOperation in experiment
The central groups in the compound XI are derived, for example, from the following compounds Z3: aliphatic alcohols such as glycerol, 1,2,4-butanetriol, 2-methyl-2-hydroxymethyl-1,3-propanediol, 2-ethyl-2-hydroxymethyl-1,3-propanediol, 1,2,3,4-butanetetrol, pentaerythritol, xylitol, mannitol and sorbitol, ...
Example 14 150 g of L-tartaric add, 700 ml of water and 20 g of Ru Mohr's salt were placed in a 1.3 l stainless steel autoclave and stirred at a hydrogen pressure of 200 bar and 80 C. until the uptake of hydrogen had ended. After cooling of the reaction mixture, removal of the catalyst by filtration and removal of the water by distillation, 123 g of a clear oil were obtained which crystallized overnight at 4 C. The resulting crystalline mass was recrystallized twice from absolute ethanol to give 86 g of L-butane-1,2,3,4-tetraol in the form of a pure-white solid (m.p. 87-88 C.; [alpha]D20 +11.6; c=2, EtOH).
The resulting meso-erythritol preparation was packed and tested in the same manner as in Example 7. As a result, it was found that the preparation had not been solidified at all.
  • 34
  • β-picroerythrin [ No CAS ]
  • [ 149-32-6 ]
  • [ 488-87-9 ]
  • 35
  • [ 149-32-6 ]
  • [ 7697-37-2 ]
  • [ 488-16-4 ]
  • [ 144-62-7 ]
  • 36
  • [ 149-32-6 ]
  • chromic acid [ No CAS ]
  • [ 64-18-6 ]
  • [ 124-38-9 ]
  • [ 144-62-7 ]
  • 37
  • [ 149-32-6 ]
  • KMnO4 [ No CAS ]
  • [ 64-18-6 ]
  • [ 124-38-9 ]
  • [ 144-62-7 ]
  • 38
  • [ 149-32-6 ]
  • silver oxide [ No CAS ]
  • aq. barium hydroxide solution [ No CAS ]
  • [ 64-18-6 ]
  • [ 124-38-9 ]
  • [ 144-62-7 ]
  • 39
  • [ 149-32-6 ]
  • [ 7697-37-2 ]
  • [ 144-62-7 ]
  • [ 87-69-4 ]
  • 40
  • [ 149-32-6 ]
  • fission fungi [ No CAS ]
  • CaCO3 [ No CAS ]
  • [ 64-18-6 ]
  • [ 110-15-6 ]
  • [ 64-19-7 ]
  • [ 107-92-6 ]
  • 41
  • [ 149-32-6 ]
  • fission fungi [ No CAS ]
  • CaCO3 [ No CAS ]
  • [ 110-15-6 ]
  • [ 64-19-7 ]
  • [ 142-62-1 ]
  • [ 107-92-6 ]
  • 42
  • [ 149-32-6 ]
  • [ 108-24-7 ]
  • [ 73977-54-5 ]
  • 43
  • (E)-2-Tributylstannanyl-but-2-ene-1,4-diol [ No CAS ]
  • [ 149-32-6 ]
  • 44
  • [ 50622-09-8 ]
  • [ 149-32-6 ]
  • 45
  • [ 6117-80-2 ]
  • [ 149-32-6 ]
  • 46
  • [ 502-44-3 ]
  • [ 149-32-6 ]
  • polymer, 4-arm star-shaped, Mw = 6665; monomer(s): DL-threitol; ε-caprolactone [ No CAS ]
  • 47
  • [ 502-44-3 ]
  • [ 149-32-6 ]
  • polymer, 4-arm star-shaped, Mw = 8450; monomer(s): DL-threitol; ε-caprolactone [ No CAS ]
  • 48
  • [ 502-44-3 ]
  • [ 149-32-6 ]
  • polymer, 4-arm star-shaped, Mw = 10166; monomer(s): DL-threitol; ε-caprolactone [ No CAS ]
  • 49
  • [ 141-46-8 ]
  • [ 149-32-6 ]
  • [ 50-70-4 ]
  • 50
  • [ 149-32-6 ]
  • [ 76-83-5 ]
  • C23H24O4 [ No CAS ]
  • 51
  • [ 492-62-6 ]
  • [ 909878-64-4 ]
  • erythrityl glucoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 2 Method for Preparing Erythrityl Glucoside 300 g of erythritol are introduced into a glass reactor equipped with a jacket through which circulates a heat transfer fluid, and with an effective stirring device. The erythritol is melted at a temperature of 145 C. 405 g of additional erythritol are dispersed in the viscous paste thus obtained and kept at 145 C. with stirring. The reaction medium thus obtained is kept at 135 C.-140 C. for a period of 30 min, with stirring, and then 173.4 g of anhydrous glucose are dispersed in this reaction medium until a fluid and homogeneous medium is obtained. The temperature is then brought back to 125 C.-130 C., and a catalytic system consisting of 1.61 g of 96% sulfuric acid is then introduced. The reaction medium is placed under a partial vacuum, of between 45 mbar and 65 mbar, and kept at a temperature of 125 C.-130 C. for a period of 4 h 30 min with simultaneous evacuation of the water formed by means of a distillation assembly. The reaction medium is then cooled to approximately 80 C. and neutralized by adding 6 g of a 30% sodium hydroxide solution so as to bring the pH of a solution containing 1% of this mixture to a value of 4.85. The mixture thus obtained has the following characteristics: appearance (visual): viscous orangey liquid; pH of a solution at 1%: 4.85; residual water: 1.4%; residual erythritol: 0.4%; residual glucose: <1%.
  • 52
  • [ 149-32-6 ]
  • cis-3,4-dihydroxytetrahydrofuran [ No CAS ]
  • 53
  • [ 149-32-6 ]
  • [ 55986-43-1 ]
  • [ 68449-27-4 ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; In toluene; EXAMPLE 29 (2,3-Dihydroxy-1-hydroxymethyl)propyl 4-(n-hexadecylamino)benzoate A mixture of 3.62 g. of 4-(-n-hexadecylamino)benzoic acid, 4.88 g. of <strong>[149-32-6]meso-erythritol</strong>, 7.60 g. of p-toluene sulfonic acid, and 100 ml. of toluene is stirred under reflux for 3 days and the water formed is collected in a Dean-Stark trap. The mixture is partitioned between aqueous sodium carbonate solution and dimethoxyethane. The organic layer is separated, dried over anhyrous magnesium sulfate, and evaporated. Crystallization from chloroform affords (2,3-dihydroxy-1-hydroxymethyl)propyl 4-(n-hexadecylamino)benzoate as a white solid, m.p. 123-125 C.
  • 54
  • [ 7558-94-3 ]
  • [ 149-32-6 ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate;Product distribution / selectivity; Example 1Electrolytic Decarboxylation of Ribonic Acid; Sodium ribonate (15 mmoles) was dissolved in 20 mL of water. Cation exchange resin (Amberlite IRC747 H+ form) was added to lower the pH from 6.8 to 3.5 (or approximately 50% neutralization of the starting material). The solution was filtered to remove the cation resin, the ribonate starting material was diluted to 30 mL, and 25 mL transferred to glass cell for electrolysis. The initial ribonate solution was analyzed by HPLC against a standard and quantified to be 9.54 mmoles (0.38M). The 25 mL of starting material containing 9.54 mmoles of ribonate was stirred in the glass cell, while a constant current of 0.5 amps (100 mA/cm2) was applied. The cell voltage averaged about 6.5 volts, and the pH of the substrate increased from 3.5 to 7.6 after 2 F/mole of charge was passed. Samples were taken at 603, 1206 and 1809 coulombs. The samples containing the erythrose product were reduced to erythritol with an excess amount of sodium borohydride, and analyzed for erythritol by HPLC-RI. The samples were quantified for erythritol based on a response factor determined from an erythritol standard, see Table 1.; Example 2 Electrolytic Decarboxylation of Arabinonic Acid; Potassium arabonate (15 mmoles) was dissolved in 20 ml of water. The arabonate was acidified to approximately 50% neutralization by adding cation exchange resin (Amberlite IRC747 H+form) and lowering the pH from 8.4 to 3.5. The arabonate was filtered to remove the resin, diluted to 30 mL, and transferred to a glass cell for electrolysis. The initial arabonate was quantified by HPLC-RI against an arabonate standard and was found to contain 9.2 mmoles (0.37M). There was a loss of 3.3 mmoles of arabonate from the cation exchange resin.The 25 mL of starting material containing 9.2 mmoles of arabonate was stirred in the glass cell, while a constant current of 0.5 amps (100 mA/cm2) was applied. The cell voltage averaged about 5.5 volts, and the pH of the substrate increased from 3.5 to 7.7 after 2 F of charge was passed per mole of starting material. Samples were taken at 603, 1206 and 1809 coulombs. The samples containing erythrose were reduced to erythritol with an excess amount of sodium borohydride, and analyzed for erythritol by HPLC-RI. The samples were quantified for erythritol based on a response factor determined from a known standard, see Table 2.
  • 55
  • [ 4440-87-3 ]
  • [ 149-32-6 ]
  • 56
  • [ 149-32-6 ]
  • [ 10024-93-8 ]
  • NdCl3*erythritol*6H2O [ No CAS ]
  • 57
  • [ 149-32-6 ]
  • [ 10099-58-8 ]
  • LaCl3*erythritol*6H2O [ No CAS ]
  • 58
  • [ 149-32-6 ]
  • [ 10361-79-2 ]
  • PrCl3*erythritol*6H2O [ No CAS ]
  • 59
  • neodymium(III) nitrate hexahydrate [ No CAS ]
  • [ 64-17-5 ]
  • [ 149-32-6 ]
  • Nd(NO3)3*erythritol*EtOH [ No CAS ]
  • 60
  • [ 497-06-3 ]
  • [ 17177-50-3 ]
  • [ 149-32-6 ]
  • 61
  • [ 497-06-3 ]
  • [ 90802-14-5 ]
  • [ 149-32-6 ]
  • [ 22554-74-1 ]
  • 63
  • [ 149-32-6 ]
  • [ 539-88-8 ]
  • ethyl levulinate bisketal of erythritol [ No CAS ]
YieldReaction ConditionsOperation in experiment
100%Chromat. sulfuric acid; at 80℃; under 40 Torr; for 3h;Product distribution / selectivity; A 500 ml 3-neck round bottom flask was charged with 36.64g (0.3 mol) erythritol (obtained from the Cargill Company of Wayzata, MN) and 346.01g (2.4 mol) ethyl levulinate (obtained from the Sigma Aldrich Company of St. Louis, MO). The flask was equipped with a Dean Stark trap, mechanical stirrer, and thermocouple. The contents of the flask were heated to 80C, at which point15.99mul of concentrated sulfuric acid (obtained from the Sigma Aldrich Company) was added to the reaction flask via a metered microliter pipette. A vacuum was applied to the reaction flask, slowly bringing the pressure down to 40 torr. This pressure was maintained with stirring while liquid was observed to collect in the Dean Stark trap. About 1 hour, 45 minutes after addition of sulfuric acid, the vacuum was released and a small sample was removed from the reaction flask. The vacuum was then reestablished. After an additional 1 hour, 15 minutes reaction time, liquid had stopped collecting in the Dean Stark trap. The vacuum was released, and the contents of the flask were allowed to cool to ambient temperature. A second sample was removed from the reaction flask.Both samples removed were analyzed by GC-MS. The GC portions of the analyses are shown in FIGS. 2 A and 2B. FIG. 2 A shows the GC of the sample removed after the initial 1 hour, 45 minutes of reaction time. FIG 2B shows the GC of the sample removed after a total of 3 hours reaction time, or an additional 1 hour, 15 minutes after the first sample was taken. The percentages of products were calculated by disregarding the presence of ethyl levulinate, because of the excess molar equivalents of ethyl levulinate used in the reaction. Thus, the percentages of erythritol, the monoketal of erythritol with one molar equivalent of ethyl levulinate, and the bisketal of erythritol with two molar equivalents of ethyl levulinate were calculated by determination of their relative GC peak areas. The sample removed at 1 hour, 45 minutes was found to contain 93.03% of the bisketal, 6.97% of the monoketal, and 0% erythritol by GC peak area. The sample removed after the additional 1 hour, 15 minutes reaction time was found to contain 100% of the bisketal.; Examplesl2-15An 896g sample of the polyketal made according to Example 3 was added to the addition flask of a short path wiped film evaporator equipped with carbon blades. A vacuum was applied to the apparatus until the pressure in the apparatus reached 100 millitorr. While under vacuum the entire apparatus was heated to 150C. The wiped film column blades were rotated at 70% at the maximum rate available on the apparatus. The cold finger of the wiped film apparatus was adjusted to O0C using a refrigerated chiller. Upon reaching the target temperature the contents of the reaction flask were dripped into the wiped film column at a rate of 160 drops/minute. After 3 hours, 15 minutes the contents of the addition flask had been emptied into the column. The non-distilled residue that was captured was analyzed by GPC, GC-MS, and 1H NMR.Using the same procedure, the compounds according to Examples 1, 5, and 6 were purified and analyzed. The results of subsequent analyses are shown in Table 2.
100%Chromat. aminosulfonic acid; at 90℃; under 30 Torr; for 8h;Product distribution / selectivity; Using the procedure of Example 1, various polyketal compounds were synthesized. Table 1 shows reagents, temperature, and time of reaction as well as the percent yield of products obtained at the end of the reaction, as determined by GC-MS (GC peak area) employing the calculation described in Example 1. Unless noted, the pressure of the reaction vessel was 30 torr during the reaction.Butyl levulinate was obtained from the Sigma Aldrich Company of St. Louis, MO. Ethyl acetoacetate was obtained from Acros Organics of Geel, Belgium. Sorbitol was obtained from Acros Organics. Mannitol was obtained from the Sigma Aldrich Company. Pentaerythritol was obtained from the Sigma Aldrich Company. Diglycerol was obtained from Tokyo Kasei Kogyo of Tokyo, Japan. Sulfamic acid was obtained from the Sigma Aldrich Company. Amberlyst-15 was obtained from the Rohm and Haas Company of Philadelphia, PA.
  • 64
  • [ 149-32-6 ]
  • [ 539-88-8 ]
  • C11H20O6 [ No CAS ]
  • ethyl levulinate bisketal of erythritol [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.46 - 6.97%Chromat.; 93.03 - 97.54%Chromat. sulfuric acid; at 80 - 90℃; under 30 - 40 Torr; for 1.75 - 4h;Product distribution / selectivity; A 500 ml 3-neck round bottom flask was charged with 36.64g (0.3 mol) erythritol (obtained from the Cargill Company of Wayzata, MN) and 346.01g (2.4 mol) ethyl levulinate (obtained from the Sigma Aldrich Company of St. Louis, MO). The flask was equipped with a Dean Stark trap, mechanical stirrer, and thermocouple. The contents of the flask were heated to 80C, at which point15.99mul of concentrated sulfuric acid (obtained from the Sigma Aldrich Company) was added to the reaction flask via a metered microliter pipette. A vacuum was applied to the reaction flask, slowly bringing the pressure down to 40 torr. This pressure was maintained with stirring while liquid was observed to collect in the Dean Stark trap. About 1 hour, 45 minutes after addition of sulfuric acid, the vacuum was released and a small sample was removed from the reaction flask. The vacuum was then reestablished. After an additional 1 hour, 15 minutes reaction time, liquid had stopped collecting in the Dean Stark trap. The vacuum was released, and the contents of the flask were allowed to cool to ambient temperature. A second sample was removed from the reaction flask.Both samples removed were analyzed by GC-MS. The GC portions of the analyses are shown in FIGS. 2 A and 2B. FIG. 2 A shows the GC of the sample removed after the initial 1 hour, 45 minutes of reaction time. FIG 2B shows the GC of the sample removed after a total of 3 hours reaction time, or an additional 1 hour, 15 minutes after the first sample was taken. The percentages of products were calculated by disregarding the presence of ethyl levulinate, because of the excess molar equivalents of ethyl levulinate used in the reaction. Thus, the percentages of erythritol, the monoketal of erythritol with one molar equivalent of ethyl levulinate, and the bisketal of erythritol with two molar equivalents of ethyl levulinate were calculated by determination of their relative GC peak areas. The sample removed at 1 hour, 45 minutes was found to contain 93.03% of the bisketal, 6.97% of the monoketal, and 0% erythritol by GC peak area. The sample removed after the additional 1 hour, 15 minutes reaction time was found to contain 100% of the bisketal.; Examples 2-11Using the procedure of Example 1, various polyketal compounds were synthesized. Table 1 shows reagents, temperature, and time of reaction as well as the percent yield of products obtained at the end of the reaction, as determined by GC-MS (GC peak area) employing the calculation described in Example 1. Unless noted, the pressure of the reaction vessel was 30 torr during the reaction.Butyl levulinate was obtained from the Sigma Aldrich Company of St. Louis, MO. Ethyl acetoacetate was obtained from Acros Organics of Geel, Belgium. Sorbitol was obtained from Acros Organics. Mannitol was obtained from the Sigma Aldrich Company. Pentaerythritol was obtained from the Sigma Aldrich Company. Diglycerol was obtained from Tokyo Kasei Kogyo of Tokyo, Japan. Sulfamic acid was obtained from the Sigma Aldrich Company. Amberlyst-15 was obtained from the Rohm and Haas Company of Philadelphia, PA.
1.00%Chromat.; 99.00%Chromat. Amberlyst-15; at 90℃; under 30 Torr; for 8h;Product distribution / selectivity; Using the procedure of Example 1, various polyketal compounds were synthesized. Table 1 shows reagents, temperature, and time of reaction as well as the percent yield of products obtained at the end of the reaction, as determined by GC-MS (GC peak area) employing the calculation described in Example 1. Unless noted, the pressure of the reaction vessel was 30 torr during the reaction.Butyl levulinate was obtained from the Sigma Aldrich Company of St. Louis, MO. Ethyl acetoacetate was obtained from Acros Organics of Geel, Belgium. Sorbitol was obtained from Acros Organics. Mannitol was obtained from the Sigma Aldrich Company. Pentaerythritol was obtained from the Sigma Aldrich Company. Diglycerol was obtained from Tokyo Kasei Kogyo of Tokyo, Japan. Sulfamic acid was obtained from the Sigma Aldrich Company. Amberlyst-15 was obtained from the Rohm and Haas Company of Philadelphia, PA.
  • 65
  • [ 149-32-6 ]
  • [ 108-10-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
91% In water at 165℃; for 16h; Inert atmosphere; oil bath; 9 Example 9 Ketalization oferythritol with methylisobutyl ketone using H7SO4 To a 50OmL 3 -neck round bottom flask equipped with a magnetic stir bar and a Dean Stark trap topped with a condenser and a nitrogen inlet/outlet were added Erythritol (50.66g, 0.42 mol, obtained from Cargill Inc. of Minnetonka, MN), methyl isobutyl ketone (MIBK, 186.22g, 1.86 mol, obtained from the Sigma- Aldrich Company of St. Louis, MO), and 98% H2SO4 (12.9μL, about 100 ppm by weight, obtained from Fisher Scientific of Waltham, MA). The Dean Stark trap was filled with excess MIBK, and the system placed under a nitrogen blanket. The flask was placed in an oil bath, and the oil bath temperature set to 165°C. The reaction was monitored by the amount of water collected in the Dean Stark trap given that water and MIBK form an azeotrope at 880C that subsequently separated into the two distinct layers. The reaction was cooled to ambient temperature after approximately 16 hours of refluxing when the theoretical amount of water had been collected. In order to neutralize the acidity, 150mesh activated, basic Al2O3 (about 23 g, or 10 wt. %, obtained from the Sigma- Aldrich Company of St. Louis, MO) was added to the flask and stirred for approximately 1 hour. The Al2O3 was removed by vacuum filtration over a sintered glass funnel. The unieacted MIBK was stripped on the rotary evaporator using a pressure of approximately 7 Torr, and sufficient heat to remove the excess MIBK. The resulting product was a clear liquid which was found to be greater than 97% pure by GC-FID, and gave a yield of about 91% based on theoretical mole percent yield. An NMR was obtained of the liquid (300MHz, CDCl3 solvent, TMS reference) and confirmed the identity of product.
  • 66
  • [ 617-35-6 ]
  • [ 149-32-6 ]
  • C14H22O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
~ 10%Chromat. With sulfuric acid; In toluene; at 110℃; for 5h; The bisketal of erythritol and ethyl pyruvate was synthesized as follows. A 1000 mL, three neck round bottom flask was charged with 122.12g (1.00 mol) erythritol (obtained from Cargill of Wayzata, MN), 348.36g (3.00 mol) ethyl pyruvate (obtained from the Sigma-Aldrich Company of St. Louis, MO), and 235g toluene (obtained from Fisher Scientific of Waltham, MA). The flask was equipped with a thermocouple, mechanical stirrer, and Dean-Stark trap with an attached condenser. A bubbler was attached to the top of the condenser of the Dean Stark trap to release positive pressure in the flask.The reaction was stirred and heated to 11O0C using a heating mantle. Upon reaching 11O0C, 29muL of concentrated sulfuric acid (obtained from the Sigma-Aldrich Company of St. Louis, MO) was quickly added by metered micropipette. A liquid was observed to collect in the Dean-Stark trap; the trapped liquid separated into two layers upon cooling. The top layer was presumed to be toluene, and the bottom layer presumed to be water. The top layer was allowed to return to the flask while the bottom layer continued to collect in the Dean-Stark trap. Heating and stirring were continued for approximately 5 hours, at which time 2/3 the theoretical amount of water had been collected in the Dean-Stark trap. The contents of the flask were allowed to cool to room temperature. The cooled contents of the flask were analyzed by GC-MS. The GC trace showed about 10% yield of the bisketal structure of erythritol and ethyl pyruvate, referred to as "EtBPEK". The toluene was stripped from the contents of the flask by rotary evaporation.
  • 67
  • [ 149-32-6 ]
  • [ 141-78-6 ]
  • [ 1015081-36-3 ]
  • 68
  • [ 149-32-6 ]
  • [ 108-24-7 ]
  • [ 7208-40-4 ]
  • [ 866394-64-1 ]
  • [ 7208-40-4 ]
  • 69
  • [ 9004-34-6 ]
  • [ 57-55-6 ]
  • [ 149-32-6 ]
  • [ 107-21-1 ]
  • [ 50-70-4 ]
  • 70
  • [ 149-32-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
32% With tris(triphenylphosphine)ruthenium(II) chloride; hydrogen bromide; hydrogen; tetrabutyl phosphonium bromide In dodecane at 200℃; for 4h; 14 Examples 11-20 General procedure: 0.5 mmol erythritol, 1.7 mmol tetrabutylphosphonium bromide (BiuPBr), 0.01 mmol Ru catalyst, 0.025 mmol HBr and 1 mL of dodecane with 0.5 mmol tetradecane as internal standard were added to the reactor. The reactor was flushed 3 times with N2 and 3 times with H2. Then the reactor was loaded with 40 bar H2 and heated to 200°C for 4 h. The conversion of erythritol was >99% in all cases.
With hydrogen In water at 119.84℃; for 144h; Autoclave;
  • 71
  • [ 564-00-1 ]
  • [ 149-32-6 ]
  • C8H16O6 [ No CAS ]
  • C8H12O4 [ No CAS ]
  • 72
  • [ 821-11-4 ]
  • [ 149-32-6 ]
  • 73
  • [ 9004-34-6 ]
  • [ 57-55-6 ]
  • [ 149-32-6 ]
  • [ 107-21-1 ]
  • [ 584-03-2 ]
  • 74
  • [ 9004-34-6 ]
  • [ 149-32-6 ]
  • [ 107-21-1 ]
  • 75
  • [ 149-32-6 ]
  • [ 84709-85-3 ]
  • 76
  • [ 50-70-4 ]
  • [ 57-55-6 ]
  • [ 149-32-6 ]
  • [ 107-21-1 ]
  • [ 56-81-5 ]
  • 77
  • [ 149-32-6 ]
  • [ 71-23-8 ]
  • [ 57-55-6 ]
  • [ 64-17-5 ]
  • [ 513-85-9 ]
  • 78
  • [ 149-32-6 ]
  • [ 66-25-1 ]
  • 2-pentyl-4-(hydroxymethyl)-1,3-dioxan-5-ol [ No CAS ]
  • C10H20O4 [ No CAS ]
  • C10H20O4 [ No CAS ]
  • 79
  • [ 110-62-3 ]
  • [ 149-32-6 ]
  • C9H18O4 [ No CAS ]
  • C9H18O4 [ No CAS ]
  • 2-butyl-4-(hydroxymethyl)-1,3-dioxan-5-ol [ No CAS ]
  • 80
  • [ 110-62-3 ]
  • [ 149-32-6 ]
  • C9H18O4 [ No CAS ]
  • C9H18O4 [ No CAS ]
  • 2-butyl-4-(hydroxymethyl)-1,3-dioxan-5-ol [ No CAS ]
  • 2,6-dibutyltetrahydro-[1,3]dioxino[5,4-d][1,3]dioxine [ No CAS ]
  • 81
  • [ 110-62-3 ]
  • [ 149-32-6 ]
  • C9H18O4 [ No CAS ]
  • 2-butyl-4-(hydroxymethyl)-1,3-dioxan-5-ol [ No CAS ]
  • 82
  • [ 110-62-3 ]
  • [ 149-32-6 ]
  • C9H18O4 [ No CAS ]
  • 2-butyl-4-(hydroxymethyl)-1,3-dioxan-5-ol [ No CAS ]
  • 2,6-dibutyltetrahydro-[1,3]dioxino[5,4-d][1,3]dioxine [ No CAS ]
  • 83
  • [ 149-32-6 ]
  • [ 124-13-0 ]
  • 2-heptyl-4-(hydroxymethyl)-1,3-dioxan-5-ol [ No CAS ]
  • C12H24O4 [ No CAS ]
  • C12H24O4 [ No CAS ]
  • 84
  • [ 112-31-2 ]
  • [ 149-32-6 ]
  • 2-nonyl-4-(hydroxymethyl)-1,3-dioxan-5-ol [ No CAS ]
  • C14H28O4 [ No CAS ]
  • C14H28O4 [ No CAS ]
  • C24H46O4 [ No CAS ]
  • 85
  • [ 112-54-9 ]
  • [ 149-32-6 ]
  • 2-undecyl-4-(hydroxymethyl)-1,3-dioxan-5-ol [ No CAS ]
  • C16H32O4 [ No CAS ]
  • C16H32O4 [ No CAS ]
  • 86
  • [ 6910-74-3 ]
  • [ 149-32-6 ]
  • C40H70N4O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With di(n-butyl)tin oxide; In 5,5-dimethyl-1,3-cyclohexadiene; for 10h;Inert atmosphere; Reflux; General procedure: The compound (I-1-1) (20.4 g), dibutyltin oxide (823 mg), 1,8-octanediol (4.12 ml), and xylene (200 ml) were added to a reaction container equipped with a stirrer, a thermometer, and a cooling tube in a nitrogen atmosphere, the mixture was stirred under heating reflux for 10 hours, and then the reaction solution was concentrated under reduced pressure. The obtained residue was dissolved in hexane (100 ml), passed through a silica gel column and an amino silica column several times, and concentrated under reduced pressure to obtain a colorless liquid compound (I-2-7) (6.02 g).
  • 87
  • [ 149-32-6 ]
  • [ 123-08-0 ]
  • C18H18O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With toluene-4-sulfonic acid; In acetone; at 70℃; for 24h; (1) Take 10g erythritol, 20g p-hydroxybenzaldehyde, 0.3 g of p-toluenesulfonic acid was dissolved in 30 g of acetone and reacted at 70 C for 24 hours., cooling to room temperature to precipitate a white precipitate, filtering, wash with a small amount of deionized water, dry it to get the intermediate, the yield was 93%.
  • 88
  • [ 149-32-6 ]
  • [ 134-96-3 ]
  • C22H26O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With toluene-4-sulfonic acid; In butanone; at 80℃; for 20h; (1) Take 10g erythritol, 25 g of syringaldehyde, 0.5g p-toluenesulfonic acid dissolved 100g of methyl ethyl ketone, the reaction was carried out at 80 C for 20 hours. The white precipitate was precipitated by cooling to room temperature, suction filtered, and washed with a small amount of deionized water. Dry it to get the intermediate, the yield was 93%.
  • 89
  • [ 149-32-6 ]
  • [ 121-33-5 ]
  • C20H22O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; Petroleum ether; at 100℃; for 0.5h; (1) Take 10g erythritol, 10g vanillin, 2g of p-toluenesulfonic acid is dissolved in 10g of N,N-dimethylformamide and 10g of petroleum ether, the reaction was carried out at 100 C for 0.5 hour. Cool to room temperature to precipitate a white precipitate, suction filtration, wash with a small amount of deionized water, then drying it to obtain an intermediate of the formula (VI), the yield is 92%.
  • 90
  • [ 4437-80-3 ]
  • [ 149-32-6 ]
  • [ 24690-44-6 ]
YieldReaction ConditionsOperation in experiment
99% With 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene In N,N-dimethyl-formamide at 25℃; for 12h; 3 Reaction Example 3: Add a stir bar, 4 mmol of IM, to a 10 ml Xulink bottle.1 mmol of 1 d, 1 ml of N,N-dimethylformamide, 0.01 mmol of organic base MTBD;After stirring at 25 ° C for 12 hours, the reaction was stopped.The reaction solution in the Xulinke bottle was dissolved in 1 ml of dichloromethane and transferred to a 25 ml round bottom single-necked flask.The Xulinke bottle was rinsed with (3 x 1 ml) dichloromethane, and the solvent was removed by heating under vacuum to give a crude product.The crude product was washed with acetone to give a white solid product was isolated in 99% yield.
  • 91
  • [ 149-32-6 ]
  • [ 50-21-5 ]
YieldReaction ConditionsOperation in experiment
67% With barium hydroxide octahydrate In methanol at 140℃; for 12h; Inert atmosphere; Sealed tube; 21 Example 21: A heterocyclic carbene iridium solid molecular catalyst 2b is used to catalyze the oxidation of erythritol to prepare lactic acid: Under the protection of nitrogen atmosphere, To a 15 mL thick-walled pressure-resistant bottle were sequentially added a nitrogen heterocyclic carbene iridium solid molecular catalyst 2b (0.003 g, 0.2 mol%), barium hydroxide octahydrate (1.89 g, 6 mmol), and erythritol (0.36 g, 3 mmol). ), methanol (2mL). After the thick-walled pressure-resistant bottle was sealed, it was placed in an oil bath and heated to 140 ° C for 12 hours. After the reaction was completed, it was cooled to room temperature, and the reaction solution was diluted with 10 mL of deionized water.And transfer the diluted reaction solution to a centrifuge tube, centrifuge at 10,000 r/min for 10 minutes. Take the supernatant and dilute with 1M H2SO4.The diluted liquid was subjected to high performance liquid chromatography to measure erythritol conversion and lactic acid yield. The erythritol conversion was 99% and the lactic acid yield was 67%.
67 %Chromat. With H2O*Ba8H16O16 In methanol at 140℃; for 12h; Sealed tube;
  • 92
  • [ 50-99-7 ]
  • [ 57-55-6 ]
  • [ 909878-64-4 ]
  • threitol [ No CAS ]
  • [ 107-21-1 ]
YieldReaction ConditionsOperation in experiment
1: 57.2% 2: 5.1% With sodium metatungstate; hydrogen; sodium hydrogencarbonate In water at 230℃; for 114h; Autoclave; 3 Example 3: Stabilization of tungsten in solution General procedure: The reactor was loaded with 0.5 gram of 1.2 wt% Ru/C (RX3-extra) (3-80 mesh) hydrogenation catalyst. The catalyst was reduced in the reactor for lhr at 300 °C under a H2 flow (3 NL/min) at atmospheric pressure (no liquid present). When the catalyst reduction was completed, the temperature was decreased to 230 °C and the pressure was increased to 100 bar. Water was fed at a rate of 60 g/L to the reactor until steady state operation was obtained. The water feed was switched to an aqueous reaction solution containing 1 wt% glucose, 2000 ppmwt NaMT, and 450 ppm NaHC03 (pH controlling agent to ran at same pH as Examples 1 and 2) without changing the feedrate of liquid or gas. These conditions were similar (except for the glucose and buffer in the feed) as the experiments described in Comparative Examples 1 and 2. The reaction ran for 115 hrs. The pH stabilized at ~5 when the flushing with water was completed. A decrease of pH was observed after switching to the aqueous reaction solution. The pH stabilized around a pH of 4.2. No significant pressure drop was observed over the product outlet exit and the liquid product stream was colorless and transparent during the entire run. It was decided to stop the experiment after 114 hrs runtime to inspect the reactor for W precipitation. No W precipitation or carbon deposits were observed in the reactor after the experiment. Typical product yields (based on HPLC analysis) are shown in Table 1.
  • 93
  • [ 909878-64-4 ]
  • [ 4358-64-9 ]
  • [ 106-97-8 ]
YieldReaction ConditionsOperation in experiment
51%; 8% With ruthenium (III) bromide; hydrogen bromide; hydrogen; tetra-n-butylphosphonium chloride; In dodecane; at 200℃; under 30003 Torr; for 4h; 0.5 mmol erythritol, 1.7 mmol tetrabutylphosphonium chloride (BU4PCI), 0.01 mmol RuBr3, 0.025 mmol HBr and 1 mL of dodecane with 0.5 mmol tetradecane as internal standard were added to the reactor. The reactor was flushed 3 times with N2 and 3 times with H2. Then the reactor was loaded with 40 bar H2 and heated to 200C for a period of 4 h. The conversion of erythritol was >99%. The main product was 1,4- anhydroerythritol (51% yield). 8% Butane was formed.
  • 94
  • [ 149-32-6 ]
  • [ 78-93-3 ]
YieldReaction ConditionsOperation in experiment
39% With hydrogen bromide; hydrogen; tetrabutyl phosphonium bromide; palladium dichloride In dodecane at 200℃; for 4h; 7 Examples 1-10 General procedure: 0.5 mmol erythritol, 1.7 mmol tetrabutylphosphonium bromide (Bu4PBr), 0.01 mmol metal catalyst, 0.025 mmol HBr and 1 mL of dodecane with 0.5 mmol tetradecane as internal standard were added to the reactor. The reactor was flushed 3 times with IN2 and 3 times with H2. Then the reactor was loaded with 40 bar H2 and heated to 200°C for 4 h. The conversion of erythritol was >99% in all cases.
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