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[ CAS No. 492-62-6 ]

{[proInfo.proName]} (Synonyms:alpha-D-glucose) ,{[proInfo.pro_purity]}

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Chemical Structure| 492-62-6

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Quality Control of [ 492-62-6 ]

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Alternatived Products of [ 492-62-6 ]

Product Details of [ 492-62-6 ]

CAS No. :	492-62-6	MDL No. :	MFCD00063774
Formula :	C₆H₁₂O₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WQZGKKKJIJFFOK-DVKNGEFBSA-N
M.W :	180.16	Pubchem ID :	79025
Synonyms :	alpha-D-glucose

Safety of [ 492-62-6 ]

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 [ 492-62-6 ]

* 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.

Upstream synthesis route of [ 492-62-6 ]
Downstream synthetic route of [ 492-62-6 ]

[ 492-62-6 ] Synthesis Path-Upstream 1~18

1
[ 57-50-1 ]
[ 492-62-6 ]
[ 470-23-5 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2013, vol. 61, # 50, p. 12265 - 12273

2
[ 529-55-5 ]
[ 492-62-6 ]
[ 480-41-1 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2013, vol. 61, # 42, p. 10026 - 10032

3
[ 492-62-6 ]
[ 56-41-7 ]
[ 56-87-1 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 13925-03-6 ]
[ 13925-07-0 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]
[ 18138-04-0 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

4
[ 492-62-6 ]
[ 56-87-1 ]
[ 56-40-6 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 17398-16-2 ]
[ 13925-07-0 ]
[ 13925-09-2 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

5
[ 492-62-6 ]
[ 56-40-6 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 17398-16-2 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

6
[ 492-62-6 ]
[ 56-87-1 ]
[ 56-40-6 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 17398-16-2 ]
[ 13925-07-0 ]
[ 13925-09-2 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

7
[ 492-62-6 ]
[ 997-62-6 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13238-84-1 ]
[ 13360-65-1 ]
[ 13925-03-6 ]
[ 13925-07-0 ]
[ 13925-09-2 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

8
[ 492-62-6 ]
[ 5051-06-9 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13238-84-1 ]
[ 13360-65-1 ]
[ 13925-03-6 ]
[ 13925-07-0 ]
[ 13925-09-2 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

9
[ 492-62-6 ]
[ 556-50-3 ]
[ 5910-89-4 ]
[ 13238-84-1 ]
[ 13360-65-1 ]
[ 160818-30-4 ]
[ 80935-98-4 ]
[ 13925-03-6 ]
[ 13925-07-0 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

10
[ 492-62-6 ]
[ 56-41-7 ]
[ 56-87-1 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 13925-03-6 ]
[ 13925-07-0 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]
[ 18138-04-0 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

11
[ 492-62-6 ]
[ 56-87-1 ]
[ 56-40-6 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 17398-16-2 ]
[ 13925-07-0 ]
[ 13925-09-2 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

12
[ 492-62-6 ]
[ 1125-88-8 ]
[ 30688-66-5 ]

Reference： [1] Australian Journal of Chemistry, 1996, vol. 49, # 3, p. 343 - 348

13
[ 71-23-8 ]
[ 492-62-6 ]
[ 645-67-0 ]

Reference： [1] Patent: CN103408422, 2016, B, . Location in patent: Paragraph 0043; 0044

14
[ 492-62-6 ]
[ 67-48-1 ]
[ 65-86-1 ]
[ 987-78-0 ]

Reference： [1] Patent: EP1939210, 2008, A1, . Location in patent: Page/Page column 15-18

15
[ 492-62-6 ]
[ 76-83-5 ]
[ 54325-28-9 ]

Reference： [1] Patent: WO2006/115312, 2006, A1, . Location in patent: Page/Page column 20
[2] Patent: US2008/39421, 2008, A1, . Location in patent: Page/Page column 4; 8

16
[ 492-62-6 ]
[ 2595-05-3 ]

Reference： [1] Synthesis, 2004, # 18, p. 2965 - 2974

17
[ 492-62-6 ]
[ 761423-87-4 ]

Reference： [1] Patent: CN108276396, 2018, A,

18
[ 492-62-6 ]
[ 951382-34-6 ]

Reference： [1] Patent: CN108276396, 2018, A,

[ 492-62-6 ] Synthesis Path-Downstream 1~68

1
[ 492-62-6 ]
[ 526-95-4 ]

Yield	Reaction Conditions	Operation in experiment
97%	With dihydrogen peroxide; iron(II) sulfate In water at 22.5℃; for 0.25h; Irradiation; Green chemistry;
	With carbon dioxide; bromine; barium carbonate ueber das δ-Lacton;
	With chromium (VI); pyridinium p-toluenesulfonate In acidic aq. solution at 30℃;

	With 1.0 wt.% Pt/TiO2 In water for 0.5h; Irradiation; Inert atmosphere;	General procedure: Photocatalytic reactions were conducted in a 180 mL Pyrex cell. The top of the cell was sealed with a silicone rubber septum. A 250W high pressure mercury lamp was used as the light source. The reaction mixture inside the cell was maintained in suspension by means of magnetic stirring. When photocatalytic activity of α-Dor β-D-glucose was investigated, the experimental process was as follows: 50 mg 1.0 wt.% Pt/TiO2 and 100 mL distilled water were added, N2 was bubbled through the mixture for 30 min to remove oxygen, and a given amount of α-D- or β-D-glucose crystal was added quickly. N2 was bubbled for another 8 min, the cell was illuminated immediately. The photocatalytic activity was determined by measuring the amount of hydrogen production for 0.5 h irradiation on a gas chromatograph (TCD, 13× molecular sieve column, N2 as gas carrier). Sampling was conducted intermittently through the septum during experiments. When the photocatalytic activity of equilibrated D-glucose solution was evaluated, the experimental process was as follows: 100 mL equilibrated D-glucose solution and 50 mg 1.0 wt.% Pt/TiO2were added to the cell. After N2 was bubbled through the mixture for 30 min, the irradiation was conducted. Other procedureswere similar to those for α-D- or β-D-glucose. The pH value of the solution was adjusted with 0.50 mol L-1 H2SO4 and 0.50 mol L-1 NaOH, and determined by a pH meter.
	With oxygen In water at 109.84℃; for 2h;
	With 5%-palladium/activated carbon In water at 50℃;
	With sodium hydroxide Electrochemical reaction;
	With glucose dehydrogenase from Bacillus subtilis; C₂₂H₂₈N₇O₁₆P₃^(4-) In aq. buffer at 30℃; Enzymatic reaction;
	With Au seeds on hallow Pt, egg-in-nest like nanomotor In water at 20℃; for 1h;

Reference： [1]Rinsant, Damien; Chatel, Gregory; Jrme, Franois [ChemCatChem, 2014, vol. 6, # 12, p. 3355 - 3359]
[2]Isbell; Pigman [Journal of Research of the National Bureau of Standards (United States), 1933, vol. 10, p. 337][Journal of Research of the National Bureau of Standards (United States), 1937, vol. 18, p. 141,167,169] Isbell; Hudson [Journal of Research of the National Bureau of Standards (United States), 1932, vol. 8, p. 329]
[3]Signorella, Sandra; Lafarga, Rubén; Daier, Verónica; Sala, Luis F. [Carbohydrate Research, 2000, vol. 324, # 2, p. 127 - 135]
[4]Zhou, Meihua; Li, Yuexiang; Peng, Shaoqin; Lu, Gongxuan; Li, Shuben [Catalysis Communications, 2012, vol. 18, p. 21 - 25]
[5]Qi, Puyu; Chen, Shasha; Chen, Jin; Zheng, Jianwei; Zheng, Xinlei; Yuan, Youzhu [ACS Catalysis, 2015, vol. 5, # 4, p. 2659 - 2670]
[6]Santhanaraj, Daniel; Rover, Marjorie R.; Resasco, Daniel E.; Brown, Robert C.; Crossley, Steven [ChemSusChem, 2014, vol. 7, # 11, p. 3132 - 3137]
[7]Xue, Zhonghua; Li, Mengqian; Rao, Honghong; Yin, Bo; Zhou, Xibin; Liu, Xiuhui; Lu, Xiaoquan [RSC Advances, 2016, vol. 6, # 16, p. 12829 - 12836]
[8]Döring, Manuel; Sieber, Volker; Simon, Robert C.; Tafertshofer, Georg; Zachos, Ioannis [Angewandte Chemie - International Edition, 2021, vol. 60, # 26, p. 14701 - 14706][Angew. Chem., 2021, vol. 133, # 26, p. 14822 - 14828]
[9]Kumar, Amit; Kumari, Nitee; Kwon, Taewan; Lee, In Su; Lim, Jongwon; Son, Chang Yun [Angewandte Chemie - International Edition, 2021, vol. 60, # 32, p. 17579 - 17586][Angew. Chem., 2021, vol. 133, # 32, p. 17720 - 17727]

2
[ 492-62-6 ]
[ 108-24-7 ]
[ 604-68-2 ]

Yield	Reaction Conditions	Operation in experiment
97.1%	With 4-methyl-morpholine; dmap; In dichloromethane; at 0 - 5℃; for 2h;	Take 1L three-port reaction bottle, install mechanical stirring, thermometer and constant pressure dropping funnel;200 ml of dichloromethane, 50 g (0.2775 mol) of d-glucose, 140.2 g (1.3875 mol) of N-methylmorpholine, 3.4 g (0.0275 mol) of DMAP were added to dissolve until dissolved; the temperature was lowered to 0-5 C, and 141.6 was slowly added. g (1.3875 mol) acetic anhydride, continue to react for 2 hours after completion; The solvent was distilled off at a high temperature, and 400 g of water was added to the reaction flask after completion, and the solid was stirred and precipitated, washed by filtration, and dried under vacuum to obtain 105.2 g of pentaacetylglucose, the yield was 97.1%;
92%	With pyridine; dmap; at 0 - 20℃; for 20h;	To (2S, 3R,4S, 5S, 6R)-6-(hyd roxymethyl)tetrahydro-2H-pyran-2, 3,4, 5-tetraol 1 (50 g, 277.7 mmol) in pyridine (500 mL) at 0 C was added DMAP (339 mg, 2.777 mmol) and acetic anhydride (500 mL). The reaction mixture was further stirred at room temperature for 20 h. After completion of the reaction, the pyridine was evaporated under reducedpressure and the residue was diluted with water and extracted with CH2CI2 (thrice). The combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude compound was purified by trituration with n-hexane to afford 100 g (92% yield) of compound 2 as off white solid.ELSD-Condition-1: [M-?-H] = 408.00; R = 2.88 mm1H NMR (400 MHz, CDCI3) 6: 6.33 (d, J = 3.91 Hz, I H), 5.47 (t, J = 10.03 Hz, I H), 5.07-5.17 (m, 2 H), 4.24-4.29 (m, I H), 4.08-4.15 (m, 2 H), 2.18 (5, 3 H), 2.09 (5, 3 H), 2.04 (5, 3 H), 2.03 (5, 3 H), 2.02 (5, 3 H).

Reference： [1]Carbohydrate Research,2008,vol. 343,p. 1814 - 1818
[2]Tetrahedron Letters,2003,vol. 44,p. 5621 - 5624
[3]Patent: CN109180662,2019,A .Location in patent: Page/Page column 8-11
[4]European Journal of Organic Chemistry,2007,p. 2769 - 2778
[5]Patent: WO2017/207754,2017,A1 .Location in patent: Page/Page column 167; 168
[6]Chemical Communications,2003,p. 1896 - 1897
[7]Tetrahedron Letters,2003,vol. 44,p. 6749 - 6753
[8]Tetrahedron,2010,vol. 66,p. 4745 - 4759
[9]Journal of the American Chemical Society,1950,vol. 72,p. 2859
[10]Chemistry - A European Journal,2002,vol. 8,p. 1670 - 1681
[11]Advanced Synthesis and Catalysis,2004,vol. 346,p. 1465 - 1470
[12]Molecules,2011,vol. 16,p. 6603 - 6620
[13]Russian Journal of Organic Chemistry,2017,vol. 53,p. 35 - 46
Zh. Org. Khim.,2017,vol. 53,p. 42 - 52,11
[14]Patent: CN108276396,2018,A .Location in patent: Paragraph 0041; 0042; 0043; 0058; 0073
[15]European Journal of Medicinal Chemistry,2020,vol. 202

3
[ 492-62-6 ]
[ 98-88-4 ]
[ 22415-91-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With pyridine; dmap; at 20℃; for 6h;	D-glucose (900 mg, 5 mmo 1),DMAP (244 mg, 2 mmol) was dissolved in anhydrous pyridine (30 mL)Benzoyl chloride (5 mL) was added,Room temperature reaction for 6 hours.After the reaction is complete,To the reaction solution was added dilute hydrochloric acid (100 ml)Ethyl acetate (30 ml X)Combine organic phase,Saturated brine (30 ml X 2)Anhydrous Na2S04 dry, concentrated,(PE: EpsilonAlpha = 3: 1)To give a white solid (3.36 g, 96%) as shown in formula (A-1).
89%	With pyridine; at 0 - 20℃; for 2.16667h;	2,3,4,6-Tetra-O-benzoyl-a-D-glucopyranosyl Benzoate (2) Benzoyl chloride (4.68 g, 33.3 mmol) was added dropwise to a solution of a-D-glucose (1.0 g, 5.6 mmol) in pyridine (30 mL) at 0C. After 10 min at 0C, the solution was stirred for 2 hrs at room temperature. The reaction was quenched by addition of cold water (50 mL) and the product extracted with EtOAc (3 x 50 ml). The combined organic layers were washed with 1 N HCI (3 x 50 mL) followed by brine (50 mL) and then dried, filtered and concentrated. The crude product was purified by recrystallisation with hot Hexane: EtOAc 2:1 to give the title compound as a white solid (3.48 g, 89%). Rf = 0.28 (Hex: EtOAc 8:2). deltaEta (CDCI3, 400 MHz): 8.16 (2H, d, J = 8.0 Hz, H-Ar), 8.02 (2H, d, J = 8.0 Hz, H-Ar), 7.94 (2H, d, J = 8.0 Hz, H-Ar), 7.88 (4H, d, J = 8.0 Hz, H-Ar), 7.66 (1 H, t, J = 8.0 Hz, H-Ar), 7.53-7.28 (14H, m, H-Ar), 6.85 (1 H, d, J = 4.0 Hz, H-1 ), 6.32 (1 H, t, J = 8.0 Hz, H-3), 5.85 (1 H, t, J = 8.0 Hz, H-4), 5.68 (1 H, dd, J = 4.0, 8.0 Hz, H-2), 4.62 (2H, m, H-6a/H-5), 4.59 (1 H, dd, J = 4.0 Hz, J = 12.0 Hz, H-6b) 5C (CDCI3, 100 MHz): 166.1 , 165.9, 165.3, 165.1 , 164.4 (C=0), [133.9, 133.5, 133.4, 133.3, 133.1 130.0, 129.9 (x2), 129.8 (x2), 129.6, 129.0, 128.9, 128.8, 128.6, 128.4 (x3), 128.37 ArC)], 90.0 (C-1 ), 76.6 (C-3), 70.5 (C-2), 70.5 (C-5), 68.9 (C-4), 62.5 (C-6)
63%	With pyridine; dmap; at 0 - 20℃; for 16h;Inert atmosphere;	BzCl (3.9 mL, 33.3 mmol) was added dropwise with stirring to D-glucose (1.0 g, 5.6 mmol) and DMAP(136 mg, 1.11 mmol) in pyridine (28 mL) at 0 C and the mixture was allowed to warm to roomtemperature. After 16 h, cold H2O (50 mL) was added and the mixture extracted with EtOAc (2 × 100mL). The combined organic layers were washed with aqueous HCl (1.0 M; 2 × 100 mL), brine (50 mL),and dried (MgSO4) and rotary evaporated to give the crude product. Recrystallization from EtOAc andhexanes gave the pentabenzoate 40 (2.46 g, 63%) as a white solid

Reference： [1]Russian Journal of Organic Chemistry,2018,vol. 54,p. 1041 - 1044
Zh. Org. Khim.,2018,vol. 54,p. 1036 - 1039,4
[2]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 2286 - 2300
[3]Patent: CN105175478,2017,B .Location in patent: Paragraph 0041; 0042
[4]Patent: WO2016/46793,2016,A2 .Location in patent: Page/Page column 33
[5]Angewandte Chemie - International Edition,2008,vol. 47,p. 2032 - 2034
[6]Tetrahedron Letters,2015,vol. 56,p. 3293 - 3297
[7]Carbohydrate Research,1987,vol. 170,p. 71 - 99
[8]Journal of Chemical Research, Miniprint,1993,p. 2663 - 2679
[9]Journal of the American Chemical Society,1950,vol. 72,p. 2200,2204
[10]Tetrahedron,2002,vol. 58,p. 7345 - 7354

4
[ 492-62-6 ]
[ 108-24-7 ]
[ 572-09-8 ]

Yield	Reaction Conditions	Operation in experiment
85.88%	With hydrogen bromide; acetic acid; at 20℃; for 11h;	General procedure: To a 500 mL round bottom flask, a-D-Glucose (5.0 g, 27.0mmol), 25 mL acetic anhydride, and 5 mL ofHBr-HOAc were added sequentially. The reaction mixture was stirred at roomtemperature with a magnetic stirring plate for 5 hrs. After 5 hrs additional 25mL of HBr-HOAc was added to the reaction mixture and the mixture was stirredfor another 6 hrs. Then 100 mL of DCM was added to the reaction mixture and itwas poured onto ice cold water. The DCM layer was separated, and water phasewas extracted with DCM (3x 20 mL). Combined organic layer was quenched withsaturated NaHCO3 solution and then with brine, dried over anhydrousNa2SO4 and concentrated. The crude product wasrecrystallized with THF-Hexanes to afford 9.8 g (85.88 %) bromide 2 as a white crystalline solid. NaN3(2.37 g, 36.45 mmol, 3 equiv) was added to a solution of 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosylbromide 2 (5 g, 12.15mmol, 1 equiv) in anhydrous DMF (25 mL). The reaction mixture was stirred at 70C under nitrogen atmosphere overnight. The mixture was filtered through aBuchner funnel and the solvent was removed under vacuum. The crude product wastaken up with water and extracted with ethyl acetate (5x20 mL). Organic layerwas dried over anhydrous Na2SO4 and concentrated. Thecrude product was purified by column chromatography with Hexane: EtOAc (15:85)to obtain the desired product 2,3,4,6-tetra-O-acetyl-beta- D -glucopyranosyl azide 3.

Reference： [1]Medicinal Chemistry Research,2011,vol. 20,p. 1465 - 1472
[2]Journal of Organic Chemistry,2005,vol. 70,p. 8687 - 8692
[3]Tetrahedron Letters,2015,vol. 56,p. 82 - 85
[4]Journal of Fluorine Chemistry,1990,vol. 46,p. 367 - 374
[5]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1001 - 1007
[6]Organic Letters,2013,vol. 15,p. 2430 - 2433

5
[ 492-62-6 ]
[ 67-64-1 ]
[ 350255-13-9 ]

Yield	Reaction Conditions	Operation in experiment
42%		To a solution of D-(+)-glucose (5.0 g, 27.7 mmol) in dryacetone (100 mL), conc. H2SO4 (4.0 mL) was added dropwise at 0C over a period of 15 min. Thereaction mixture was stirred at ambient temperature for about 6 h. Aqueous NaOH solution (7 g in 8 mLH2O) was added in ice cold condition followed by 1.5 g solid NaHCO3 to neutralize the excess acid ifpresent and stirred for overnight at room temperature. Next day it was filtered and concentrated in rotaryevaporator. The yellow viscous liquid obtained was dissolved in 50 mL chloroform and washed withwater (1 x 20 mL). The organic portion was separated and dried over anhydrous Na2SO4. The solvent wasremoved in a rotary evaporator under reduced pressure at room temperature. Finally 50 mL petroleumether was added to this liquid oil and solid needle shape crystals were formed after stored it in deep fridgefor overnight. The crystals wre collected through filtration, dried well and used directly without furtherpurification. Thus diacetonide glucose was obtained in an isolated yield of 42% (3.0 g, 11.5 mmol).

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 42 - 52
[2]Natural Medicines,2019,vol. 73,p. 163 - 172
[3]Phytochemistry,1987,vol. 26,p. 1453 - 1458
[4]ChemSusChem,2018,vol. 11,p. 292 - 298

6
[ 531-75-9 ]
[ 492-62-6 ]
[ 305-01-1 ]

Reference： [1]Journal of the Indian Chemical Society,1983,vol. 60,p. 507 - 508

7
[ 492-62-6 ]
[ 1125-88-8 ]
[ 30688-66-5 ]

Reference： [1]Australian Journal of Chemistry,1996,vol. 49,p. 343 - 348

8
[ 3767-28-0 ]
[ 492-62-6 ]
[ 100-02-7 ]

Yield	Reaction Conditions	Operation in experiment
	With α-glycosidase; C40H59Cu2N12O5(1+); In methanol; acetonitrile;pH 10.5;Enzymatic reaction;Kinetics;	General procedure: The glycosidase-like activity was determined by measuring the hydrolysisof <strong>[3767-28-0]4-nitrophenyl-α-D-glucopyranoside</strong> and 4-nitrophenyl-β-D-glucopyranoside hydrolysis. The hydrolysis product 4-nitrophenolewas produced which could be detected by monitoring the increase ofan strong absorbance at 410 nm (ε is pH dependent).Initially, the extinction coefficients of the product formation of4-nitrophenolate in a multicomponent buffer were calculated by calibrationcurves for each pH value (pH=5.5-11.5) using Lambert Beer'slaw(Table 1). The extinction coefficients of pH=8.7-11.5 are similar tothose determined for 4-nitrophenolate in CAPS buffer (ε = 16,190 M-1 cm-1) [10]. The obtained extinction coefficients (see Supporting Information)were used to convert the absorbance of the reaction productinto molar amounts.UV-Vis-spectra data were recorded on a Jasco V-570 spectrophotometerequipped with a Jasco ETC-505 T cryostat at 25 C and in a0.3: 1.3: 1 MeCN:buffer:MeOH solution. Using time-course measurementsat fixed wavelengths (λmax = 410 nm), spectrophotometrictitrations were performed with a cyclic pseudo-peptide concentrationof 1 mM (MeOHdry). CuII(CF3SO3)2 (25 mM, MeOHdry) andbase (n-Bu4N)(OMe) (25 mM, MeOHdry) were added to differentpH-samples. The final concentrations of dicopper(II) complexesof H4pat1 and H4pat2 in the cuvette were 40 μM. All solutions weredegassed and kept under argon at 7 C. Blank tests, the autohydrolysisof <strong>[3767-28-0]4-nitrophenyl-α-D-glucopyranoside</strong> or 4-nitrophenyl-β-D-glucopyranoside respectively, were subtracted from the reportedkinetic rates. For the determination of pH dependent reaction velocities the substrate concentration of 30 mM (MeOHdry) was chosen. Forsubstrate dependency measurements at constant pH the substrateconcentration was varied between 1 and 50 mM.
	With α-glucosidase on Caco-2 cells from colon carcinoma; In aq. phosphate buffer; at 37℃; for 1.5h;pH 7.4;Enzymatic reaction;	The α-glucosidase activity of Caco-2 was analyzed using a modifiedversion of a published procedure.34 Caco-2 cells were seeded on eachwell of 24-well plastic plates (1.5×105/well). The cells were culturedin MEM medium (FBS(+), P/S(+)) for 1, 2, and 3 weeks at 37 C. Priorto enzyme assay, the culture medium was washed with PBS twice, andthen the cells were loaded with 1mM of 4-nitrophenyl α-D-glucopyranosidedissolved in 0.10 mol/L of PBS buffer (12 mmol/L of phosphate,137 mmol/L of NaCl, 2.7 mmol/L of KCl, pH 7.4) and kept at37 C in a CO2 incubator. The absorption was measured at 400 nm usinga UV microplate reader (PerkinElmer EnSpire) for each incubationtime (0, 10, 30, 60, and 90 min). The assay was performed in duplicate,and the average value reported.

Reference： [1]Bioscience, Biotechnology and Biochemistry,2001,vol. 65,p. 2058 - 2064
[2]Journal of Natural Products,2011,vol. 74,p. 314 - 320
[3]Angewandte Chemie - International Edition,2012,vol. 51,p. 7449 - 7453
[4]Tetrahedron,2015,vol. 71,p. 9415 - 9419
[5]Journal of Inorganic Biochemistry,2016,vol. 159,p. 70 - 75
[6]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 859 - 864
[7]Journal of the Chemical Society of Pakistan,2019,vol. 41,p. 714 - 721

9
[ 492-62-6 ]
[ 67-64-1 ]
[ 582-52-5 ]

Yield	Reaction Conditions	Operation in experiment
64.7%	With sulfuric acid; for 6h;Cooling with ice;	Using a 1 L round bottomflask, 30 g (0.17 mol) of anhydrous alpha-D-glucose was addedin 0.6 L of acetone. The mixture was stirred vigorously in an ice-water bath. Concentrated H2SO4 (30mL) was added dropwise for 6 hours. After all the acid was added, the solution was cooled to 0C and neutralized by 50% aqueous potassium hydroxide solution to maintain the pH of the solution near 7. After stirring overnight, thesolution was filtered, and the solvent was removed under reduced pressure. Thesolid was dissolved in 100 mL of dichloromethane and the solution was washed with100 mL of water. The aqueous phase was then extracted three times with 100 mL ofdichloromethane. The organic layers were combined and then concentrated underreduced pressure. Recrystallization from petroleumether gave 28 g of white crystals(64.7% yield).1H NMR (500 MHz, Chloroform-d) delta: 5.94 (d, J = 3.6 Hz, 1 H), 4.53 (d, J = 3.7 Hz, 1 H), 4.39-4.29 (m, 2H), 4.16 (dd, J = 8.7, 6.2 Hz, 1 H), 4.06 (dd,J = 7.6, 2.8 Hz, 1 H), 3.98 (dd, J = 8.6, 5.4 Hz, 1 H), 2.65 (d, J = 3.7 Hz, 1 H), 1.49 (s,3H), 1.44 (s, 3H), 1.36 (s, 3H), 1.31 (s, 3H). 13C NMR (126 MHz, Chloroform-d) delta:111.96, 109.79, 105.42, 85.22, 81.27, 75.34, 73.61, 67.80, 26.99, 26.90, 26.32, 25.28.
55%	With sulfuric acid; copper(II) sulfate; at 0 - 20℃; for 30.16h;	D-Glucose (30 g, 166.5 mmol) was added to dry acetone (600 mL) at room temperature and wasfollowed by anhydrous CuSO4 (30 g, 610.60 mmol). The reaction mixture was cooled to 0 C,and conc. H2SO4 (22 mL, 0.66 molar in acetone) was added drop-wise over a period of 10 min.The reaction mixture was stirred at room temperature for 30 h. After completion, (TLC) reaction mixture was neutralized with a saturated solution of K2CO3. The solution was filtered and thefiltrate was evaporated under reduced pressure. The residue thus obtained was extracted withchloroform and dried over anhydrous Na2SO4, concentrated under reduced pressure to afford ayellowish solid, which was recrystallized from chloroform: hexane (1:9) to to afford the productglucose-di-acetone (GDA) S9 (24 g, 55%) as white crystals.
42%	With zinc(II) chloride;iodine; at 20℃; for 21h;Heating / reflux;	To 305 g (1.69 mol) of powdered D-glucose in 2.5 L of acetone (99.9%) is added 500 g (3.67 mol) of anhydrous ZnCl2 and 12 g (0.047 mol) of iodine. The mixture is stirred for 16 hrs at RT and then 5 hrs at reflux. It is then neutralised with 50% NaOH solution (336 g in 330 mL) and addition of sodium thiosulphate solution (23 g). The precipitated salts are filtered off through celite and the precipitate washed with acetone three times. The acetone is evaporated and the residue redissolved in dichloromethane and washed with water two times. After drying with MgSO4 and evaporation of the organic phase the desired product is crystallised from boiling hexane. This yields 185.3 g (42%).

Reference： [1]Nucleosides, nucleotides and nucleic acids,2016,vol. 35,p. 479 - 494
[2]Beilstein Journal of Organic Chemistry,2017,vol. 13,p. 1106 - 1118
[3]Patent: WO2006/129075,2006,A1 .Location in patent: Page/Page column 48
[4]Journal of the American Chemical Society,2009,vol. 131,p. 1658 - 1659
[5]Synthesis,2004,p. 2965 - 2974

10
[ 492-62-6 ]
[ 28917-43-3 ]
α-D-glucopyranose-1,2,3,4,6-pentakis[3,5-bis(phenylmethoxy)benzoate] [ No CAS ]
β-D-glucopyranose-1,2,3,4,6-pentakis[3,5-bis(phenylmethoxy)benzoate] [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 2829 - 2837

11
[ 492-62-6 ]
[ 1570-05-4 ]
β-D-glucopyranose-1,2,3,4,6-pentakis[3,4-bis(phenylmethoxy)benzoate] [ No CAS ]
α-D-glucopyranose-1,2,3,4,6-pentakis[3,4-bis(phenylmethoxy)benzoate] [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 2829 - 2837

12
[ 492-62-6 ]
[ 87-99-0 ]
xylityl glucoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 1 Method for Preparing Xylityl Glucoside 703.0 g of xylitol are introduced into a glass reactor equipped with a jacket through which circulates a heat transfer fluid, and equipped with an effective stirring device. The xylitol is melted at a temperature of 135 C., and the viscous paste thus obtained is cooled to 115 C. Glucose is then added gradually to the reaction medium so as to allow it to disperse homogeneously. An acid catalytic system consisting of 1.29 g of 96% sulfuric acid is added to the mixture thus obtained. The reaction medium is placed under a partial vacuum of 90 mbar to 45 mbar, and kept at a temperature of 100 C.-105 C. for a period of 4 h 30 min with evacuation of the water formed by means of a distillation assembly. The reaction medium is then cooled to 95 C.-100 C. and neutralized by adding 5 g of sodium hydroxide at 30%, so as to bring the pH of a solution containing 1% of this mixture to a value of 5.0. The characteristics of the mixture thus obtained are as follows: appearance (visual): orange wax at ambient temperature; pH solution at 1%: 5.0; residual xylitol: 55.8%; residual glucose: <1%.

Reference： [1]Patent: US2006/88491,2006,A1 .Location in patent: Page/Page column 3

13
[ 492-62-6 ]
[ 56-81-5 ]
glyceryl glucoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		COMPARATIVE EXAMPLE Method for Preparing Glyceryl Glucoside 1650.0 g of glycerol are introduced into a glass reactor equipped with a jacket through which circulates a heat transfer fluid, and equipped with an effective stirring device. The glycerol is brought to 80 C. and 646.0 g of anhydrous glucose are gradually dispersed until a fluid and homogeneous medium is obtained. The reaction medium is kept at 85 C. for a period of 30 minutes, with stirring, and then 4.65 g of 98% sulfuric acid are introduced. The reaction medium is then brought to 100 C., placed under a partial vacuum of between 60 and 30 mbar, and maintained for 4 hours with concomitant evacuation of the water formed in situ by the reaction. The reaction medium is then cooled to approximately 80 C. and neutralized by adding 24 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 6.1. The composition thus obtained has the following characteristics: appearance (visual): viscous yellow liquid; pH solution at 1%: 6.1 residual glycerol: 42.4% residual glucose: <1%

Reference： [1]Patent: US2006/88491,2006,A1 .Location in patent: Page/Page column 4

14
[ 492-62-6 ]
[ 909878-64-4 ]
erythrityl glucoside [ No CAS ]

Yield	Reaction Conditions	Operation 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%.

Reference： [1]Patent: US2006/88491,2006,A1 .Location in patent: Page/Page column 3 - 4

15
[ 492-62-6 ]
[ 67-48-1 ]
[ 65-86-1 ]
[ 987-78-0 ]

Yield	Reaction Conditions	Operation in experiment
		Example 2; Purification of CDP-choline from culture of microorganism having an activity to produce CDP-choline; Escherichia coli MM294/pCKG55 strain (FERM BP-3717) having enzyme activities of PyrG, CCT and CKI was inoculated to a test tube containing L medium (10 mL) [liquid medium containing bactotripton (10 g/L; manufactured by Difco), yeast extract (5 g/L; manufactured by Difco) and NaCl (5 g/L) and adjusted to pH 7.2] supplemented with ampicillin (50 mug/mL), and cultured with shaking at 25C, 300 rpm for 24 hours. The culture thus obtained (20 mL) was inoculated to 2 L of conical flask with baffles containing L medium (400 mL) supplemented with ampicillin (50 mug/mL) and cultured with rotary shaking at 25C, 190 rpm for 16 hours. The culture thus obtained (125 mL) was inoculated to a 5 L culture bath containing a liquid medium (2.5 L; nonadjusted pH) with a composition of glucose (5 g/L; separately sterilized), peptone (5 g/L; manufactured by Kyokuto Pharmaceutical Industrial), Na2HPO4 (6 g/L), KH2PO4 (3 g/L), NaCl (5 g/L), NH4Cl (1 g/L), MgSO4·7H2O (250 mg/L; separately sterilized) and vitamin B1 (4 mug/L; separately sterilized), and cultured with shaking at 600 rpm under culture condition of airflow 2.5 L/minute, at 25C for 11 hours and then at 32C for 13 hours, while adjusting the mixture to pH 7.0 with 14% aqueous ammonia. During culturing, a feed solution having a composition of glucose (167 g/L), peptone (167 g/L) was fed with a peristaltic pump at a rate of 30 mL/hours during the period of from 11 hours to 24 hours from the start of the culturing. On the other hand, Corynebacterium·ammoniagenes ATCC21170 strain having an activity to produce UTP from <strong>[65-86-1]orotic acid</strong> was inoculated to a test tube containing a liquid medium (10 mL) having a composition of glucose (50 g/L), polypeptone (10 g/L; manufactured by Daigo Eiyo Chemicals), yeast extract (10 g/L; manufactured by Daigo Eiyo Chemicals), urea (5 g/L), (NH9)2SO4 (5 g/L), KH2PO4 (1 g/L), K2HPO4 (3 g/L), MGSO4·7H2O (1 g/L), CaCl2·2H2O (0.1 g/L), FeSO4·7H2O (10 mg/L), ZnSO4·7H2O (10 mg/L), MnSO4·4 - 6H2O (20 mg/L), L-cysteine (20 mg/L), calcium D-pantothenate (10 mg/L), vitamin B1 (5 mg/L), nicotinic acid (5 mg/L) and biotin (30 mug/L; adjusted to pH 7.2 with sodium hydroxide), and cultured with reciprocal shaking at 300 rpm at 28C for 24 hours. The culture thus obtained (20 mL) was inoculated to a 2 L conical flask with baffle containing a liquid medium (230 mL) having the same composition as the above-mentioned, and cultured with rotary shaking at 190 rpm at 28C for 24 hours. The culture thus obtained (250 mL) was inoculated to a 5 L culture bath containing a liquid medium (2.5 L) having a composition of glucose (100 g/L), meat extract (10 g/L), polypeptone (10 g/L), KH2PO4 (1 g/L), K2HPO4 (1 g/L), MgSO4.7H2O (1 g/L), CaCl2·2H2O (0.1 g/L) , FeSO4·7H2O (20 mg/L), ZnSO4·7H2O (10 mg/L), MnSO4·4 - 6H2O (20 mg/L), beta-alanine (15 mg/L), L-cysteine (20 mg/L), biotin (100 mug/L), urea (2 g/L; separately sterilized) and vitamin B1 (5 mg/L; separately sterilized) (adjusted to pH 7.2 with sodium hydroxide) and seed-cultured with shaking at 600 rpm at 32C under culture condition of airflow 2.5 L/minute while adjusting the mixture to pH 6.8 with concentrated aqueous ammonia. At the time point when glucose in the supernatant of the above-mentioned seedculture medium was consumed, the culture (350 mL) was aseptically collected, inoculated to a 5 L culture bath containing a liquid medium (2.5 L) having a composition of glucose (180 g/L), KH2PO4 (10 g/L), K2HPO4 (10 g/L), MgSO4·7H2O (10 g/L), CaCl2·2H2O (0.1 g/L), FeSO4·7H2O (20 mg/L), ZnSO4·7H2O (10 mg/L), MnSO4·4 - 6H2O (20 mg/L; separately sterilized), beta-alanine (15 mg/L), L-cysteine (20 mg/L), sodium glutamate (1 g/L), biotin (100 mug/L), urea (2 g/L; separately sterilized) and vitamin B1 (5 mg/L; separately sterilized) (adjusted to pH 7.2 with sodium hydroxide) and main-cultured with shaking at 600 rpm at 32C under culture condition of airflow 2.5 L/minute while adjusting the mixture to pH 6.8 with concentrated aqueous ammonia. The culturing was ceased at the time point when glucose in the culture supernatant was consumed. The culture (360 mL) of Escherichia coli MM294/pCKG55 strain and the culture (360 mL) of Corynebacterium·ammoniagenes ATCC21170 strain thus obtained were placed in a 2 L culture bath, glucose (100 g/L), <strong>[65-86-1]orotic acid</strong> (10 g/L), choline chloride (8.4 g/L), MgSO4·7H2O (5 g/L) and xylene (20 mL/L) were added thereto, and distilled water was added to allow the total amount to be 800 mL. The mixture was reacted with shaking at 800 rpm at 32C under the condition of airflow 0.8 L/minute while adjusting the mixture to pH 7.2 with 10N sodium hydroxide. During the reaction, KH2PO4 was added as appropriate to keep the concentration of phosphoric acid in the supernatant of the reaction mixture at 1 - 5 g/L as KH2PO4. The reaction was carried out for 23 hours to obtain 11.0 g/L of CDP-choline. Four batche...

Reference： [1]Patent: EP1939210,2008,A1 .Location in patent: Page/Page column 15-18

Yield	Reaction Conditions	Operation in experiment
		Example 6Sythesis of a Polyol EsterThis Example sets forth a representative synthesis of a polyol ester mixture from vegetable oils and the hydrogenolysis product mixture obtained by hydrogenolysis of sorbitol.A polyol sample (200 g) from the hydrogenolysis of sorbitol containing, by weight percent, 0.25% glucose; 0.25% xylose; 0.25% arabinose; 1.74% arabitol; 1.24% erythritol; 6.47% lactate; 10.45% glycerol; 1.00% 1,2,4-butanetriol; 42.54% ethylene glycol; 32.34% propylene glycol; 1.00% 2,3-butanediol; 0.5% 1,3-butanediol; and 2.00% 1,2-butanediol was combined with dried corn oil (200 g) and sodium inethoxide (1.0 g) in a 1000 mL round bottom flask. The mixture was heated with agitation at 120 C. for 4 hours. The product was cooled and neutralized with citric acid. Hexane was added and the organic layer was recovered. The hexane was removed from the product using a rotary evaporator under reduced pressure to give a residue of polyol esters of corn oil fatty acids, If desired, the product can be stripped using a wiped film evaporator/miiolecular still at 90 C., 0.6 millibars, 270 rpm and a flow rate of 4 mL/min. The resulting polyol ester composition is suitable for use as a 100% biobased replacement for a petroleum derived propylene glycol monoester.

17
[ 50-70-4 ]
[ 6763-34-4 ]
[ 492-62-6 ]
[ 57-55-6 ]
[ 18826-95-4 ]
[ 3068-00-6 ]
[ 107-21-1 ]
[ 56-81-5 ]
[ 513-85-9 ]
[ 584-03-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; hydrogen;nickel-rhenium-on-carbon; In water; at 220℃; under 31029.7 - 62059.4 Torr; for 4h;Product distribution / selectivity;	Example 5Polyester Polymerization ReactionThis Example sets forth a representative polyester polymerization reaction using a hydrogenolysis product mixture obtained by hydrogenolysis of glycerol or sorbitol according to certain embodiments disclosed herein.A composition enriched in compounds containing two hydroxyl groups was obtained by hydrogenolysis of glycerol by passing a 40% solution of crude glycerol obtained as a by-product of a palm biodiesel synthesis through a reactor substantially as set forth in Example 1. The reactor product was dewatered by distillation. A composite was prepared by combining four dewatered glycerol hydrogenolysis product samples to yield a mixture of polyols having the composition: 75.5% propylene glycol, 4.5% ethylene glycol, 1.8% lactic acid, 12.2% glycerol, and 0.5% water. This composition was subjected to short path distillation to reduce the water content to 0.15% and the undi stilled residue enriched in compounds containing two hydroxyl groups (Mixture 1) had the following composition: 75.8% propylene glycol, 4.7% ethylene glycol, 1.8% lactic acid, 1.3% 2,3-butanediol, and 13.8% glycerol.In one study, the composition enriched in compounds containing two hydroxyl groups is combined with an equimolar quantity of diisocyanate to make a predominantly linear polyurethane using the procedure set forth by Frisch (?Fundamental Chemistry and Catalysis of Polyirrethanes,? Frisch, K. C., in Polyurethane Technology, Paul Bruins, ed., Interscience Publishers, New York, 1969, the disclosure of which is incorporated in its entirety by reference herein).In a second study, the hydrogenolysis product from the hydrogenolysis of sorbitol containing, by weight percent, 0.25% glucose; 0.25% xylose; 0.25% arabinose; 1.74% arabitol; 1.24% erythritol; 6.47% lactate; 10.45% glycerol; 1.00% 1,2,4-butanetriol; 42.54% ethylene glycol; 32.34% propylene glycol; 1.00% 2,3-butanediol; 0.50% 1,3-butanediol; and 2.00% 1,2-butanediol is combined with a diisocyanate at 100 C. to make a branched polymer.The polymers resulting from study 1 and 2 will be suitable for use in fibers, hard and soft elastomers, coatings and adhesives, flexible and rigid foams, and thermoplastics and thermosetting plastics.; Example 6Sythesis of a Polyol EsterThis Example sets forth a representative synthesis of a polyol ester mixture from vegetable oils and the hydrogenolysis product mixture obtained by hydrogenolysis of sorbitol.A polyol sample (200 g) from the hydrogenolysis of sorbitol containing, by weight percent, 0.25% glucose; 0.25% xylose; 0.25% arabinose; 1.74% arabitol; 1.24% erythritol; 6.47% lactate; 10.45% glycerol; 1.00% 1,2,4-butanetriol; 42.54% ethylene glycol; 32.34% propylene glycol; 1.00% 2,3-butanediol; 0.5% 1,3-butanediol; and 2.00% 1,2-butanediol was combined with dried corn oil (200 g) and sodium inethoxide (1.0 g) in a 1000 mL round bottom flask. The mixture was heated with agitation at 120 C. for 4 hours. The product was cooled and neutralized with citric acid. Hexane was added and the organic layer was recovered. The hexane was removed from the product using a rotary evaporator under reduced pressure to give a residue of polyol esters of corn oil fatty acids, If desired, the product can be stripped using a wiped film evaporator/miiolecular still at 90 C., 0.6 millibars, 270 rpm and a flow rate of 4 mL/min. The resulting polyol ester composition is suitable for use as a 100% biobased replacement for a petroleum derived propylene glycol monoester.

Reference： [1]Patent: US2008/103340,2008,A1 .Location in patent: Page/Page column 14

19
[ 67-56-1 ]
[ 492-62-6 ]
[ 64-17-5 ]
[ 71-36-3 ]
[ 67-47-0 ]
[ 1917-64-2 ]
[ 1917-65-3 ]
[ 1917-68-6 ]

Yield	Reaction Conditions	Operation in experiment
	In water at 190℃; for 0.00666667 - 0.0516667h;	2 Example 2. Mixed ethers formation from fructose (or glucose) and mixed alcohols- continuous flow experiment; A 1.25 wt% solution of sugar (Frc or GIc) in methanol/ethanol/n-butanol/water 23/45/23/9 v/v/v/v, was flowed through a fixed bed (200 μl) of a catalyst at 1900C. Flow rates were selected such to achieve a space velocity of 0.25 or 0.5 min"1, i.e. a contact time of 2 or 4 min.In all cases tBMF was detected by HPLC and identified by LC-MS (Cl) in the effluent stream. Conversion of substrate, selectivity and yield of furan derivatives were calculated using the same method as for the batch reactions.
	In water at 150℃; for 1h;	3 Example 3; In a batch experiment, 0.36 mmol of substrate (glucose, fructose or HMF) and 6.5 mg of a solid acid catalyst were mixed in a reactor coated inside with Teflon.0.8 ml of alcohols mixture (Methanol, Ethanol and n-Butanol with 1/2/1 volume ratio) was added and pressurized at 12.5 bar with nitrogen. The reaction was performed at different temperatures and different reaction time. Four main peaks were observed in the UV spectrum and identified as HMF, 5-(ethoxymethyl)furfural (EMF), 5-(methoxymethyl)furfural (MMF) and 5- (butoxymethyl)furfural nBuMF. In this experiment and in the experiment of Example 4, the selectivity was calculated slightly different, based on the formula: Selectivity = 100 * nt (product) / [n0 (substrate) - nt (substrate)]Where: n0- the initial number of moles nt- the number the moles of a compound at time "t".The results are listed in Table 3.
	In water at 150℃; for 1h;	3 Example 3; In a batch experiment, 0.36 mmol of substrate (glucose, fructose or HMF) and 6.5 mg of a solid acid catalyst were mixed in a reactor coated inside with Teflon.0.8 ml of alcohols mixture (Methanol, Ethanol and n-Butanol with 1/2/1 volume ratio) was added and pressurized at 12.5 bar with nitrogen. The reaction was performed at different temperatures and different reaction time. Four main peaks were observed in the UV spectrum and identified as HMF, 5-(ethoxymethyl)furfural (EMF), 5-(methoxymethyl)furfural (MMF) and 5- (butoxymethyl)furfural nBuMF. In this experiment and in the experiment of Example 4, the selectivity was calculated slightly different, based on the formula: Selectivity = 100 * nt (product) / [n0 (substrate) - nt (substrate)]Where: n0- the initial number of moles nt- the number the moles of a compound at time "t".The results are listed in Table 3.

Reference： [1]Current Patent Assignee: AVANTIUM N.V. - WO2009/30508, 2009, A2 Location in patent: Page/Page column 9
[2]Current Patent Assignee: AVANTIUM N.V. - WO2009/30508, 2009, A2 Location in patent: Page/Page column 9-10
[3]Current Patent Assignee: AVANTIUM N.V. - WO2009/30508, 2009, A2 Location in patent: Page/Page column 9-10

20
[ 67-56-1 ]
[ 57-48-7 ]
[ 6763-34-4 ]
[ 492-62-6 ]
[ 64-17-5 ]
[ 71-36-3 ]
[ 98-01-1 ]
[ 67-47-0 ]
[ 1917-64-2 ]
[ 1917-65-3 ]
[ 1917-68-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 11.8% 2: 6.9% 3: 7.5% 4: 7.6% 5: 2.6%	at 150℃; for 1h;	3 Example 3In a typical experiment, 65 mg of a mixture of xylose, glucose and fructose (1 :1 :1 , mass ratios) and 6.5 mg of a solid acid catalyst were mixed in a reactor coated inside with Teflon. 0.8 ml of an alcohol mixture (Methanol, Ethanol and n-Butanol with 1/2/1 volume ratio) was added and pressurized at 12.5 bar with nitrogen. The mixture reacted under for 1 h at 150 0C. The main peaks observed in the UV spectrum were identified as F, HMF, EMF, MMF and nBuMF.Table3
1: 9.8% 2: 0.3% 3: 5.5% 4: 5.3% 5: 1.9%	at 150℃; for 1h;	3 Example 3In a typical experiment, 65 mg of a mixture of xylose, glucose and fructose (1 :1 :1 , mass ratios) and 6.5 mg of a solid acid catalyst were mixed in a reactor coated inside with Teflon. 0.8 ml of an alcohol mixture (Methanol, Ethanol and n-Butanol with 1/2/1 volume ratio) was added and pressurized at 12.5 bar with nitrogen. The mixture reacted under for 1 h at 150 0C. The main peaks observed in the UV spectrum were identified as F, HMF, EMF, MMF and nBuMF.Table3
1: 5.3% 2: 1.3% 3: 6.2% 4: 6.1% 5: 2%	at 150℃; for 1h;	3 Example 3In a typical experiment, 65 mg of a mixture of xylose, glucose and fructose (1 :1 :1 , mass ratios) and 6.5 mg of a solid acid catalyst were mixed in a reactor coated inside with Teflon. 0.8 ml of an alcohol mixture (Methanol, Ethanol and n-Butanol with 1/2/1 volume ratio) was added and pressurized at 12.5 bar with nitrogen. The mixture reacted under for 1 h at 150 0C. The main peaks observed in the UV spectrum were identified as F, HMF, EMF, MMF and nBuMF.Table3

1: 3.3% 2: 2.1% 3: 6.2% 4: 6.4% 5: 1.7%	at 150℃; for 1h;	3 Example 3In a typical experiment, 65 mg of a mixture of xylose, glucose and fructose (1 :1 :1 , mass ratios) and 6.5 mg of a solid acid catalyst were mixed in a reactor coated inside with Teflon. 0.8 ml of an alcohol mixture (Methanol, Ethanol and n-Butanol with 1/2/1 volume ratio) was added and pressurized at 12.5 bar with nitrogen. The mixture reacted under for 1 h at 150 0C. The main peaks observed in the UV spectrum were identified as F, HMF, EMF, MMF and nBuMF.Table3
1: 4.4% 2: 1.9% 3: 5.1% 4: 5% 5: 1.6%	at 150℃; for 1h;	3 Example 3In a typical experiment, 65 mg of a mixture of xylose, glucose and fructose (1 :1 :1 , mass ratios) and 6.5 mg of a solid acid catalyst were mixed in a reactor coated inside with Teflon. 0.8 ml of an alcohol mixture (Methanol, Ethanol and n-Butanol with 1/2/1 volume ratio) was added and pressurized at 12.5 bar with nitrogen. The mixture reacted under for 1 h at 150 0C. The main peaks observed in the UV spectrum were identified as F, HMF, EMF, MMF and nBuMF.Table3
1: 5.6% 2: 1.6% 3: 5.3% 4: 5.2% 5: 1.5%	at 150℃; for 1h;	3 Example 3In a typical experiment, 65 mg of a mixture of xylose, glucose and fructose (1 :1 :1 , mass ratios) and 6.5 mg of a solid acid catalyst were mixed in a reactor coated inside with Teflon. 0.8 ml of an alcohol mixture (Methanol, Ethanol and n-Butanol with 1/2/1 volume ratio) was added and pressurized at 12.5 bar with nitrogen. The mixture reacted under for 1 h at 150 0C. The main peaks observed in the UV spectrum were identified as F, HMF, EMF, MMF and nBuMF.Table3
1: 5.1% 2: 5.4% 3: 4.2% 4: 5.1% 5: 0.8%	at 150℃; for 1h;	3 Example 3In a typical experiment, 65 mg of a mixture of xylose, glucose and fructose (1 :1 :1 , mass ratios) and 6.5 mg of a solid acid catalyst were mixed in a reactor coated inside with Teflon. 0.8 ml of an alcohol mixture (Methanol, Ethanol and n-Butanol with 1/2/1 volume ratio) was added and pressurized at 12.5 bar with nitrogen. The mixture reacted under for 1 h at 150 0C. The main peaks observed in the UV spectrum were identified as F, HMF, EMF, MMF and nBuMF.Table3

Reference： [1]Current Patent Assignee: AVANTIUM N.V. - WO2009/30511, 2009, A1 Location in patent: Page/Page column 9
[2]Current Patent Assignee: AVANTIUM N.V. - WO2009/30511, 2009, A1 Location in patent: Page/Page column 9
[3]Current Patent Assignee: AVANTIUM N.V. - WO2009/30511, 2009, A1 Location in patent: Page/Page column 9
[4]Current Patent Assignee: AVANTIUM N.V. - WO2009/30511, 2009, A1 Location in patent: Page/Page column 9
[5]Current Patent Assignee: AVANTIUM N.V. - WO2009/30511, 2009, A1 Location in patent: Page/Page column 9
[6]Current Patent Assignee: AVANTIUM N.V. - WO2009/30511, 2009, A1 Location in patent: Page/Page column 9
[7]Current Patent Assignee: AVANTIUM N.V. - WO2009/30511, 2009, A1 Location in patent: Page/Page column 9

21
[ 6763-34-4 ]
[ 492-62-6 ]
[ 64-17-5 ]
[ 98-01-1 ]
[ 67-47-0 ]
[ 1917-65-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 24.6% 2: 0.3% 3: 4.3%	at 150℃; for 1h;	1 Example 1 In a typical experiment, 32.5 mg of xylose, 32.5 mg glucose or fructose and 0.8 ml of ethanol were added in a reactor coated inside with Teflon. The mixture reacted under nitrogen (12.5 bar) in the presence of a solid acid catalyst (6.5 mg) for 1 h at 150 0C. The three main peaks observed in the UV spectrum were identified as Furfural (F), 5-(hydroxymethyl)furfural (HMF) and 5-(ethoxymethyl)furfural EMF. Table 1.
1: 23.2% 2: 4.8% 3: 11.5%	at 150℃; for 1h;	1 Example 1 In a typical experiment, 32.5 mg of xylose, 32.5 mg glucose or fructose and 0.8 ml of ethanol were added in a reactor coated inside with Teflon. The mixture reacted under nitrogen (12.5 bar) in the presence of a solid acid catalyst (6.5 mg) for 1 h at 150 0C. The three main peaks observed in the UV spectrum were identified as Furfural (F), 5-(hydroxymethyl)furfural (HMF) and 5-(ethoxymethyl)furfural EMF. Table 1.
1: 7.9% 2: 2.1% 3: 5.7%	at 150℃; for 1h;	1 Example 1 In a typical experiment, 32.5 mg of xylose, 32.5 mg glucose or fructose and 0.8 ml of ethanol were added in a reactor coated inside with Teflon. The mixture reacted under nitrogen (12.5 bar) in the presence of a solid acid catalyst (6.5 mg) for 1 h at 150 0C. The three main peaks observed in the UV spectrum were identified as Furfural (F), 5-(hydroxymethyl)furfural (HMF) and 5-(ethoxymethyl)furfural EMF. Table 1.

Reference： [1]Current Patent Assignee: AVANTIUM N.V. - WO2009/30511, 2009, A1 Location in patent: Page/Page column 8-9
[2]Current Patent Assignee: AVANTIUM N.V. - WO2009/30511, 2009, A1 Location in patent: Page/Page column 8-9
[3]Current Patent Assignee: AVANTIUM N.V. - WO2009/30511, 2009, A1 Location in patent: Page/Page column 8-9

22
[ 492-62-6 ]
[ 64-19-7 ]
[ 67-47-0 ]
[ 10551-58-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 1.8% 2: 6.9%	In H-3-methylimidazolium bis(trifluoromethanesulfonyl)imide; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride at 100℃; for 3h;	1 Example 1In a" batch experiment, 50 mg of substrate (glucose or fructose) and 250 mg of 1-Ethyl-3- methylimidazolium chloride (EMIM) or 500 mg of a mixture of EMIM and H-3- methylimidazolium bis(trifluoromethanesulfonyl)imide (HMIM) were loaded in a Teflon lined reactor with 7.5 ml volume. 1 ml of acetic acid was added and the mixture reacted under nitrogen (12.5 bar) in the presence of CrCI2 as catalyst for 3 h at 100 0C. Two products were observed in the UV spectra and identified as HMF and 5-acetoxy methyl furfural (AMF). Selectivities and conversions for catalysts used in this example can be found in table below.The substrate conversions and the selectivities and yields were calculated according to the formulas:Conversion = 100* [n0 (substrate) - nt (substrate)] / n0 substrate Selectivity = 100 * nt (product) / [n0 (substrate) - nt (substrate)]Yield = 100 * nt (product) / n0 substrate,Where: n0- the initial number of moles nt- the number the moles of a compound at time "t".
1: 1.3% 2: 5.1%	In 1-ethyl-3-methyl-1H-imidazol-3-ium chloride at 100℃; for 3h;	1 Example 1In a" batch experiment, 50 mg of substrate (glucose or fructose) and 250 mg of 1-Ethyl-3- methylimidazolium chloride (EMIM) or 500 mg of a mixture of EMIM and H-3- methylimidazolium bis(trifluoromethanesulfonyl)imide (HMIM) were loaded in a Teflon lined reactor with 7.5 ml volume. 1 ml of acetic acid was added and the mixture reacted under nitrogen (12.5 bar) in the presence of CrCI2 as catalyst for 3 h at 100 0C. Two products were observed in the UV spectra and identified as HMF and 5-acetoxy methyl furfural (AMF). Selectivities and conversions for catalysts used in this example can be found in table below.The substrate conversions and the selectivities and yields were calculated according to the formulas:Conversion = 100* [n0 (substrate) - nt (substrate)] / n0 substrate Selectivity = 100 * nt (product) / [n0 (substrate) - nt (substrate)]Yield = 100 * nt (product) / n0 substrate,Where: n0- the initial number of moles nt- the number the moles of a compound at time "t".

Reference： [1]Current Patent Assignee: AVANTIUM N.V. - WO2009/30512, 2009, A2 Location in patent: Page/Page column 7
[2]Current Patent Assignee: AVANTIUM N.V. - WO2009/30512, 2009, A2 Location in patent: Page/Page column 7

23
[ 492-62-6 ]
[ 67-47-0 ]

Yield	Reaction Conditions	Operation in experiment
78.4%	With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate; 4-methyl-2-pentanone; In water; at 120℃; under 1900.13 Torr; for 6h;Autoclave;	The as-received glucose was dried for 24h at 90C prior to dehydration reaction. Experiments were carried out in a Teflon-lined stainless steel autoclave equipped with a heating jacket. After the catalysts (typically 0.3g) and glucose (0.7g) were added into the autoclave pre-charged with water and 4-methyl-2-pentanone (MIBK) (typically 8mL), the reaction was started under spontaneous pressure by heating the mixture to the reaction temperature. After the reaction, the reactor was removed and quickly quenched in a cool water bath. Subsequently, filtration, extraction, and separation were conducted; and then the organic and aqueous phases were collected to characterize the products. For the recycling of IL-5, HMF was extracted out from the water phase 5 times with 8mL of ethyl acetate, after extraction, the aqueous phase was heated at 60C for 24h in a vacuum oven to remove water and residual ethyl acetate. The IL-5 was then used directly for the next run by adding glucose and MIBK. All results were replicated at least three times.
52.6%	With copper-Cr/ZSM-5 zeolite; In dimethyl sulfoxide; at 140℃; for 6h;	The catalytic reaction was taken place in a 150mL pressurized reactor. 0.5g (o.d.) of glucose was placed in a beaker. Aspecific amount of catalyst to gether with 20mL of solvent were added. The mixture was then treated with ultrasound for15 min before it was transferred to the reactor. The reactor wasplaced in a glycerin bath, which was set at 120-140C andkept there for 2-8h according to experimental design. Afterreaction time, the reactor was cooled down to room temperature.Products were separated from each other by centrifugation.The liquid part was collected and stored in a glass bottleat 4C for sugar analysis using an HPLC (High PerformanceLiquid Chromatogaphy) Agilent 1200 system located at theLaboratory of Food Technology (HUST). Working conditions were set as follows: temperature 5-50C, humidity 5-96%,and using GLP/GMP compliance as standard. The system isequipped with a G1322A vacuum pump; an Aminex HPX-87P column; the stationary phase was in lead form with particlesize of 9mum, 8% cross linkage; mobile phase was ionizedwater, which was filtered through a 0.45mum filter and degassed,working well at pH 5-9. Obtained data were analyzed with anAgilent 2D LC ChemStation software (G2170BA).
41.5%	chromium dichloride; In octane; ISOPROPYLAMIDE; at 108 - 127℃; for 1h;	EXAMPLE 16Preparation of hydroxymethylfurfural (HMF) (16)279 g of n-octane was poured into the boiling area to boil. After, the temperature and flow rate of the boiling area, the reaction area and the dehydration distillation area were stable. Meanwhile, a sugar solution containing 10.004 g of glucose, 0.440 g of chromium(II) chloride (CrCl2, catalyst) and 91.285 g of dimethylacetamide (DMAc) was continuously conducted into the reaction area with a flow rate of 4.1 ml/min until 22 min. At that time, the temperature of the boiling area was 127 C., the temperature of the reaction area was 124 C. and the temperature of the top of the dehydration distillation area was 108 C. The reaction was completed after 60 min. After cooling, the HPLC was analyzed. In the fourth organic layer, the content of the hydroxymethylfurfural (HMF) was 33.7 mg/ml. In the first organic layer, the content of the hydroxymethylfurfural (HMF) was 10.1 mg/ml. The glucose conversion rate was 98.4%. Using GC analysis, in the third and second organic layers, the content of the hydroxymethylfurfural (HMF) was nearly zero. The weight of the fourth organic layer was 75.24 g. The weight of the first organic layer was 19.46 g. The final hydroxymethylfurfural (HMF) product was 2.907 g with a yield of 41.5 mol %.

32%	With Amberlyst 15; at 24.84℃; for 2h;Ionic liquid; Inert atmosphere;	A suitable amount of carbohydrate (0.025 g) was weighed in a round bottom flask containing the pure IL or IL binary mixture (0.5 g). To favor carbohydrate dissolution, the mixture was stirred at 353 K for 30 min under argon. In all cases, the mixtures appeared to be homogeneous after this treatment. After equilibration at the reaction temperature, the suitable amount of acidic catalyst (0.025 g for fructose and glucose and 0.05 g for sucrose) was added. After reaction time, each sample was diluted with 0.250 g of ultra pure water, stirred at room temperature and diluted with methanol in such a way to have a 5-HMF concentration ranging from 7 × 10-6 M up to 7 × 10-5 M. The concentration of 5-HMF was determined from UV absorbance recorded at 277 nm. The presence of 5-HMF in the reaction mixture, as single UV absorbing product, was further verified by means of TLC on silica gel by comparison with a standard sample (eluent: ethyl acetate/methanol 5:1, v/v).
	With hydrogenchloride;Sn-Beta zeolite; In tetrahydrofuran; water; at 180℃; for 1.16667h;Product distribution / selectivity;	The results of glucose to HMF conversion experiments are summarized in the following table:
	With chromium(III) chloride hexahydrate; tetraethylammonium bromide; at 95 - 120℃;	Example 3In this example, the conversion of glucose to FDCA was performed. The direct conversion of glucose to FDCA in a triphasic reactor is more challenging than the conversion of fructose to FDCA, as glucose needs to be isomerized to fructose.In the triphasic reactor (shown in Fig. Sb), 0.18 g glucose (1 mmol), 0.91 g TEAB, 0.09 ml water, 0.018 g smashed amberlyst-15 and 0.0266 g CrC136H20 (0.1 mmol) were added to phase I of the reactor to convert glucose to HMF. TEAB was used as the reaction media and amberlyst-15/CrC13 was selected as catalysts.Phase I was initially conducted at 95C. However, after 7 hours of reaction, only negligible amount of FDCA was detected, with the glucose conversion at only 7.2%. The low glucose conversion may due to the low reaction temperature in phase I.The reaction in phase I was improved upon by conducting the reaction at 120C for 30 mm. To achieve this, the triphasic reactor setup was tilted to heat only the phase I chamber of the reactor. After that, the temperature was lowered down to 95C, and the whole reactor was heated in the same oil bath. 0.25 g Au8Pd2/HT catalyst, 0.106 g of Na2CO3 (1 mmol), and 10 ml of water were used in the other side of reactor (phase III).4 ml of MIBK was added on top of phase I and phase III.Oxygen was bubbled in reactor III during the reaction, with water added if the water level decreased.In this example, 50.2% of FDCA yield was achieved with a full conversion of glucose. The results are shown in Table 1 below.

Reference： [1]RSC Advances,2016,vol. 6,p. 11176 - 11184
[2]ChemSusChem,2014,vol. 7,p. 1647 - 1654
[3]Chinese Chemical Letters,2014,vol. 25,p. 757 - 761
[4]RSC Advances,2013,vol. 3,p. 9201 - 9205
[5]RSC Advances,2017,vol. 7,p. 7555 - 7559
[6]Carbohydrate Research,2011,vol. 346,p. 956 - 959
[7]ChemCatChem,2017,vol. 9,p. 2739 - 2746
[8]RSC Advances,2013,vol. 3,p. 20085 - 20090
[9]Green Chemistry,2013,vol. 15,p. 85 - 90
[10]Chinese Journal of Chemistry,2015,vol. 33,p. 583 - 588
[11]Catalysis science and technology,2015,vol. 5,p. 2496 - 2502
[12]Green Chemistry,2012,vol. 14,p. 2506 - 2512
[13]Catalysis Letters,2020,vol. 150,p. 170 - 177
[14]ChemSusChem,2013,vol. 6,p. 61 - 64
[15]Patent: US2012/16141,2012,A1 .Location in patent: Page/Page column 7
[16]Catalysis Letters,2014,vol. 144,p. 2121 - 2128
[17]RSC Advances,2018,vol. 8,p. 31618 - 31627
[18]Applied Catalysis A: General,2014,vol. 482,p. 287 - 293
[19]New Journal of Chemistry,2016,vol. 40,p. 7958 - 7967
[20]Green Chemistry,2010,vol. 12,p. 321 - 325
[21]Journal of the American Chemical Society,2009,vol. 131,p. 1979 - 1985
[22]Chinese Journal of Chemistry,2010,vol. 28,p. 1773 - 1776
[23]Patent: US2011/207923,2011,A1 .Location in patent: Page/Page column 12
[24]Patent: US2011/207923,2011,A1
[25]Patent: US2011/207923,2011,A1
[26]ChemSusChem,2012,vol. 5,p. 783 - 789
[27]ChemSusChem,2012,vol. 5,p. 1388 - 1391
[28]Chemistry - A European Journal,2014,vol. 20,p. 12298 - 12309
[29]Patent: WO2016/53186,2016,A1 .Location in patent: Page/Page column 13; 14
[30]Research on Chemical Intermediates,2016,vol. 42,p. 6757 - 6767
[31]ChemSusChem,2016,vol. 9,p. 2089 - 2096

24
[ 492-62-6 ]
[ 3282-30-2 ]
[ 1213234-53-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With pyridine; dmap; thionyl chloride; In dichloromethane; at 48 - 50℃; for 2h;Reflux; Large scale;	10L four-mouth reaction flask by adding 384g alpha-D-glucose, pyridine, dichloromethane, 4-dimethylaminopyridine, mechanical stirring, heated to 48 C. The heating was switched off and 10 ml of thionyl chloride was added. Start dropping 1412g of pivaloyl chloride, 2h drop is completed, the temperature maintained 50 reflux reaction. HPLC Detection of Central Control. After completion of the reaction, the solution was concentrated to dryness under negative pressure, and the mixture was stirred with dichloromethane and dilute hydrochloric acid to dissolve, and the mixture was allowed to stand and separate. The organic phase was washed with water, dried over anhydrous Na? SO? And filtered. The organic phase was concentrated under vacuum to dryness to give 1830 g of a pale yellow solid. The crude product was recrystallized from absolute ethanol to give 1096 g of a white solid of 98% purity in 82% yield.
	With triethylamine;dmap; In dichloromethane; at 20℃; for 0.75h;Inert atmosphere;	Example 8 (2R,3R,4S,5R,6R)-6-(pivaloyloxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetrakis(2,2-dimethylpropanoate) D-glucose (25.0 g, 0.139 mol) was suspended in anhydrous dichloromethane (416 mL) under nitrogen and the resulting mixture was stirred for 5 minutes at room temperature, then cooled to 0 C. and stirred for 10 minutes. To the resulting mixture was then added TEA (154.7 mL), dropwise over about 10-15 min, with stirring; then DMAP (1.25 g, 0.0102 mol) in one portion. To the resulting mixture was added pivaloyl chloride (136 mL) diluted with dichloromethane (83 mL) at 0 C., over 30 min. The ice bath was removed and the resulting mixture stirred at room temperature for 20 hours. The resulting mixture was then poured into dichloromethane (500 mL) and hydrochloric acid (1.5M, 375 mL) and the resulting phases separated. The organic layer was washed with sodium bicarbonate solution (550 g in 500 mL DI water, 1N) and then evaporated to a small volume. To the resulting residue was added ethanol (95%, 240 mL) and the mixture heated to reflux temperature to yield a homogeneous mixture. The resulting mixture was cooled to 0 C., resulting in the formation of white crystals, which were filtered and dried in vacuo at room temperature, overnight, to yield the title compound.
	With triethylamine;dmap; In dichloromethane; at 0 - 20℃; for 20.5h;Inert atmosphere;	Example 8(2R,3R,4S,5R,6R)-6-(pivaloyloxymethyl)tetrahvdro-2H-pyran-2,3,4,5-tetrayl-dimethylpropanoate)D-glucose (25. Og, 0.139 mol) was suspended in anhydrousdichloromethane (416 mL) under nitrogen and the resulting mixture was stirred for 5 minutes at room temperature, then cooled to 0C and stirred for 10 minutes. To the resulting mixture was then added TEA (154.7 mL), dropwise over about 10-15 min, with stirring; then DMAP (1 .25 g, 0.0102 mol) in one portion. To the resulting mixture was added pivaloyl chloride (136 mL) diluted with dichloromethane (83 mL) at 0C, over 30 min. The ice bath was removed and the resulting mixture stirred at room temperature for 20 hours. The resulting mixture was then poured into dichloromethane (500 mL) and hydrochloric acid (1 .5M, 375 mL) and the resulting phases separated. The organic layer was washed with sodium bicarbonate solution (550 g in 500mL Dl water, 1 N) and then evaporated to a small volume. To the resulting residue was added ethanol (95%, 240 mL) and the mixture heated to refluxtemperature to yield a homogeneous mixture. The resulting mixture was cooled to 0C, resulting in the formation of white crystals, which were filtered and dried in vacuo at room temperature, overnight, to yield the title compound.

With pyridine; dmap; at 0 - 25℃; for 13h;

To a solution of D-glucose (1.5 g; 8.32 mmol) in dry pyridine (20 mL) and DMAP (0.2 g), pivaloyl chloride (5.64 ml; 45.79 mmol) was added dropwise at 0 C and the resulting mixture was stirred at the same temperature for 1 h and then for 12 h at room temperature. Solvent was evaporated off and the residue chromatographed on a silica gel column with hexane/ethyl acetate (25:1) as the eluting solvent to give penta-O-pivaloyl-alpha-D-glucopyranoside as a white solid, m.p. 152-154 C. 1H NMR (500 MHz, CDCl3) delta 5.70 (d, J = 8.3 Hz, 1H), 5.37 (t, J = 9.4 Hz, 1H), 5.23-510 (m, 2H), 4.18-4.05 (m, 2H), 3.86 (dd, J = 9.6, 3.9 Hz, 1H), 1.20 (s, 9H), 1.17 (s, 9H), 1.15 (s, 9H), 1.11 (s, 18H). LCMS (ESI possitive) m/z: 601 [M+H]+.

Reference： [1]Patent: CN103980263,2016,B .Location in patent: Paragraph 0061
[2]Patent: US2011/87017,2011,A1 .Location in patent: Page/Page column 34
[3]Patent: WO2012/140120,2012,A1 .Location in patent: Page/Page column 89-90
[4]Tetrahedron Letters,2020,vol. 61

25
[ 67-56-1 ]
[ 492-62-6 ]
[ 624-45-3 ]

Yield	Reaction Conditions	Operation in experiment
18%Chromat.	With aluminium(III) chloride hexahydrate; at 160℃; under 750.075 Torr; for 2.5h;Inert atmosphere; Autoclave;	General procedure: An 80 mL teflon-lined stainless steel autoclave reactor was firstcharged with methanol (15 mL), and then a certain amount of carbohydrate and catalyst was added under stirring. After the auto-clave was sealed, the atmosphere over the solution was replaced with N2 for four times and then the pressure of N2 was charged to 0.1 MPa. Subsequently, the reactor was heated to the desired temperature under stirring. When the reaction was over, the reac-tor was cooled down to the ambient temperature. The products in the reaction solution were identified by an Agilent 6890 N GC/5973MS and a Shimadzu LC-20AT HPLC analysis system. Conversion ofglucose was analyzed with the external standard method on a Shi-madzu LC-20AT HPLC analysis system equipped with an AminexHPX-87H column (300 × 7.8 mm) and refractive index detector(RID-10A). 0.005 M aqueous H2SO4was used as the mobile phase,which had a flow rate of 0.6 mL/min. The column temperature was 40C. Yields of MLA and MLE were analyzed on a GC equipped withan FID detector using naphthalene as the internal standard.
	With SBA-15-SO3H; tin-containing molecular sieve; In water; at 170℃; for 7h;High pressure;	A mixture of 1 part of alpha-glucose, 20 parts of methanol, 0.1 part of SBA-15-SO3H and 0.1 g of Sn-Beta was placed in a hydrothermal reactor and heated at 170 C for 7 hours. After cooling, the yield was measured by gas chromatography (GC) the yield of methyl levulinate was 61 mol%.

Reference： [1]Green Chemistry,2014,vol. 16,p. 785 - 791
[2]Green Chemistry,2011,vol. 13,p. 1676 - 1679
[3]Journal of Molecular Catalysis A: Chemical,2014,vol. 388-389,p. 74 - 80
[4]Patent: CN103408422,2016,B .Location in patent: Paragraph 0039; 0040

26
[ 492-62-6 ]
[ 56-65-5 ]
[ 58-64-0 ]
[ 59-56-3 ]

Yield	Reaction Conditions	Operation in experiment
	With recombinant galactokinase from Streptococcus pneumoniae TIGR4; magnesium chloride; at 45℃; for 3h;pH 8;aq. buffer; Enzymatic reaction;Kinetics;	General procedure. The activity of recombinant GalKSpe4 toward Gal, Glc, N-acetylgalactosamine (GalNAc) and N-acetylglucosamine (GlcNAc) was assayed in a cocktail containing 50 mM Tris-HCl (pH 8.0), 5 mM MgCl2, 5 mM <strong>[56-65-5]ATP</strong> and proper amount of GalKSpe4 at 45 C for 3 h. The reaction was terminated by boiling the mixture for 5 min followed by centrifugation. The supernatant was analyzed by normal phase silica gel thin-layer chromatography with the phase being n-butanol/acetic acid/water (2:1:1, v/v/v).

Reference： [1]Carbohydrate Research,2011,vol. 346,p. 2421 - 2425

27
[ 10338-51-9 ]
[ 492-62-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; In methanol; at 90.0℃; for 3.0h;	General procedure: Each glycoside (1 mg) was dissolved in 2% NaOMe/MeOH (1 ml) at room temperature. After 1 h, the reaction mixture was neutralized by passing each through an ion-exchange resion (Amberlite IRA 400, H+ form) column. These were then heated in 1 M HCl (2 ml) at 90 C for 3 h. After cooling, each reaction mixture was neutralized by individually passing each through an ion-exchange resin (Amberlite IRA 400, OH- form) column. Each filtrate was thentransferred to a Sep-Pak C18 cartridge and eluted with H2O and MeOH, and the H2O eluated were individuals concentrated and the residued were treated with L-cysteine methyl ester hydrochloride (2 mg) in pyridine (0.25 ml) at 60 C for 1 h. After the reaction, the solution was treated with TMS-HT (100 ll, hexamethyldisilazane and trimethylchlorosilamine in pyridine, TOKYO KASEI Co., Tokyo, Japan) at 40 C for 10 min. The reaction mixture was then subjected to GLC analysis to identify the derivatives of D-glucose from 5, 6, 7 and 8. GLC conditions: column, ULBON HR-1, 25 m x 0.25 mm (i.d.), 0.25 lm; detector, FID; injector temperature, 250 C; detector temperature, 280 C; column temperature,250 C for 0.5 min and then 1.5 C/min up to 270 C; He carrier,24 cm/s; D-glucose tR, 6.83 min, respectively.

Reference： [1]Phytochemistry,2011,vol. 72,p. 2244 - 2252

28
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[ 56-41-7 ]
[ 56-87-1 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 13925-03-6 ]
[ 13925-07-0 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]
[ 18138-04-0 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 4697 - 4708

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[ 72-18-4 ]
[ 56-87-1 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13360-65-1 ]
[ 18138-05-1 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]
[ 32736-94-0 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 4697 - 4708

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[ 56-87-1 ]
[ 56-40-6 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 17398-16-2 ]
[ 13925-07-0 ]
[ 13925-09-2 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 4697 - 4708

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[ 997-62-6 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13238-84-1 ]
[ 13360-65-1 ]
[ 13925-03-6 ]
[ 13925-07-0 ]
[ 13925-09-2 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 4697 - 4708

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[ 5051-06-9 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13238-84-1 ]
[ 13360-65-1 ]
[ 13925-03-6 ]
[ 13925-07-0 ]
[ 13925-09-2 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 4697 - 4708

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[ 492-62-6 ]
[ 556-50-3 ]
[ 5910-89-4 ]
[ 13238-84-1 ]
[ 13360-65-1 ]
[ 160818-30-4 ]
[ 80935-98-4 ]
[ 13925-03-6 ]
[ 13925-07-0 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 4697 - 4708

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[ 492-62-6 ]
[ 56-40-6 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 17398-16-2 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 4697 - 4708

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[ 492-62-6 ]
[ 842133-18-0 ]

Reference： [1]Patent: WO2012/140120,2012,A1
[2]Patent: CN103980263,2016,B
[3]Patent: CN109111490,2019,A

36
[ 492-62-6 ]
[ 36097-08-2 ]
N-2-(6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluorooctylthio)ethyl-D-glucopyranosylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;Raney-Ni; In methanol; at 60℃; under 8274.59 Torr; for 12h;	Example 1 N-2-(6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluorooctylthio)ethyl-D-glucopyranosylamine, 1 This example illustrates the synthesis of Compound 1, an example of a compound of formula (I).A 200 mL shaker tube containing a mixture of 2-(1H,1H,2H,2H-perfluorooctylthio)ethylamine (5.8 g, 0.0137 mol), D-glucose (2.25 g, 0.0125 mol), Raney-Ni catalyst (1.5 g slurry, 0.75 g catalyst), and methanol (40 mL) was agitated at 60 C. for 12 h under an H2 atmosphere (160 psi). The catalyst was then removed by filtration of the reaction mixture through Celite. The filtrate was concentrated under vacuum to obtain 6.2 g (82% yield) of a white solid. The crude product was recrystallized from diethyl ether/ethanol (10:1) to obtain 1.7 g of a pale yellow solid 1: LC-MS (API-ES+), major peak M+H=586; 19F NMR (DMSO-d6): delta -81.3 (m, 3F), -113.8 (m, 2F), -122.3 (m, 2F), -123.2 (m, 2F), -123.4 (2F), -126.4 (m, 2F); 13C NMR (DMSO-d6) delta 126 MHz, delta (for non-fluorinated carbons): 91.03, 78.0, 74.3, 73.6, 71.2, 61.6, 45.9, 32.0, 31.4 (t, 2JCF=68.8 Hz), 20.1.

Reference： [1]Patent: US2012/309854,2012,A1 .Location in patent: Page/Page column 6

37
[ 492-62-6 ]
[ 37091-73-9 ]
2-glucosyl-1,3-dimethylimidazolinium chloride [ No CAS ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 7608 - 7610

38
[ 529-55-5 ]
[ 492-62-6 ]
[ 480-41-1 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2013,vol. 61,p. 10026 - 10032

39
[ 492-62-6 ]
[ 54258-41-2 ]
[ 1544526-95-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With ammonium sulfate; In methanol; at 65℃; for 24h;	General procedure: 4.2.1.4. Method D. A stirred solution of the 5-amino-1,10-phenanthroline (195 mg, 1 mmol), the monosaccharide (3 mmol) and ca. 4 mg of (NH4)2SO4 in 16 mL of MeOH was heated at 65 C for 24 or 48 h. During this time a pale yellow precipitate was accumulated. The reaction mixture was cooled and the solid obtained was separated by filtration and washed with MeOH (2 x 10 mL) and H2O (2 x 10 mL) to eliminate excess of sugar and possible traces of the starting amine and/or other by-products as well to remove the (NH4)2SO4 salt, followed by Et2O. This protocol provided pure N-(1,10-phenanthrolin-5-yl)-beta-glycopyranosyl amines 2a, 2c and 2d. For derivatives 2b and 2e the starting sugar could not be completely removed and a subsequent purification was required. The product was preadsorbed on silica gel and purified by flash chromatography. After drying in vacuum the purity of the products was checked by TLC, 1H NMR and analytical data. Derivatives 2a-e were obtained as monohydrates and exhibited poor solubility in water and organic solvents.

Reference： [1]Tetrahedron,2014,vol. 70,p. 1071 - 1076

40
[ 57-50-1 ]
[ 492-62-6 ]
[ 470-23-5 ]
[ 470-69-9 ]
[ 13133-07-8 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2013,vol. 61,p. 12265 - 12273

41
[ 120221-14-9 ]
[ 492-62-6 ]

Reference： [1]Carbohydrate Research,2014,vol. 385,p. 9 - 17

42
[ 492-62-6 ]
[ 1119-72-8 ]

Yield	Reaction Conditions	Operation in experiment
		Microbial synthesis of cis,cis-muconate from D-glucose utilizing E. coli AB2834/pKD136/pKD8.243A/pKD8.292 proceeded as follows. One liter of LB medium (in 4 L Erlenmeyer shake flask) containing IPTG (0.2 mM), ampicillin (0.05 g), chloramphenicol (0.02 g) and spectinomycin (0.05 g) was inoculated with 10 mL of an overnight culture of AB2834/pKD136/pKD8.243A/pKD8.292. Cells were grown at 250 rpm for 10 h at 37 C. The cells were harvested, resuspended in 1 L of M9 minimal medium containing 56 mM D-glucose, shikimic acid (0.04 g), IPTG (0.2 mM), ampicillin (0.05 g), chloramphenicol (0.02 g) and spectinomycin (0.05 g). The cultures were returned to 37 C. incubation. After resuspension in minimal medium the pH of the culture was closely monitored, particularly over the initial 12 h. When the culture reached a pH of 6.5, 5 N NaOH was added to adjust the pH back to approximately 6.8. Over the 48 h accumulation period, the culture was not allowed to fall below pH 6.3. After 24 h in minimal medium 12 mM cis,cis-muconate and 1 mM protocatechuate were detected, using methods described in Example 2, in the culture supernatant along with 23 mM D-glucose. After 48 h in minimal medium AB2834/pKD136/pKD8.243A/pKD8.292 had replaced the 56 mM D-glucose with 17 mM cis,cis-muconate.

Reference： [1]Patent: US8809583,2014,B2 .Location in patent: Paragraph 0095

43
[ 492-62-6 ]
[ 107-21-1 ]

Yield	Reaction Conditions	Operation in experiment
88.8%		A pyrolysis product composition comprising C1-C3 oxygenate compounds was obtained by pyrolysis of a 10 wt% agueous glucose (D-glucose monohydrate; Sigma Aldrich) solution as described in US 7,094,932 B2. The composition of the pyrolysis product composition is given in Table 1.Table 1: Composition of the pyrolysis product composition of Example 1.Examples 2-4:The pyrolysis product composition of Example 1 and described in Table 1 (15.5 g) was loaded into an autoclave along with 5% Ru on carbon catalyst (Sigma Aldrich, 0.20 g). The autoclave was purged 3 times with hydrogen and sub-sequently pressurized with hydrogen to the respective pressures given in Table 2. The mixture was heated to 80C from room temperature over the course of 15 min and stirred for 6 hours. The autoclave was then cooled to room temperature and the decrease in hydrogen pressure was noted.The hydrogenated product mixture was isolated from the catalyst by filtration and analyzed by HPLC and GC.The maximum theoretical yield of ethylene glycol was based on hydrogenation of both glyoxal and glycolaldehyde to ethylene glycol.Table 2Examples 2-4 illustrate the significantly increased yield of ethylene glycol with an increase in reaction pressure. Additionally Example 4 demonstrates the low yield of 1,2- BDO produced by the process of the present invention in comparison to the preparation of ethylene glycol via the hydrogenolysis route as illustrated by US 20080228014 Al [1,2-BDO:ethylene glycol ratio of 0.08].
	With 1% Ru/SiO2; hydrogen; In water; at 195℃; under 22502.3 - 63756.4 Torr;Inert atmosphere;	Example 1 30 ml deionized water, 0.300 g of a catalyst consisting of W (10.88) -Ni (3.63) -Pt (0.05) and Zr02 and 0.300 g of a catalyst consisting of Ru(1.0%) on Si02 catalyst were charged into a 60 ml autoclave equipped with a gas stirrer and hydrogen supply. The autoclave was closed, the gas phase was replaced by nitrogen, then by hydrogen and the autoclave was pressurised to 30 bara pressure. The autoclave was stirred at 1450 rpm, heated to 195 C in 15 minutes and pressurised with hydrogen to 75 bara pressure. 5 ml of a solution of 20%wt glucose in water was fed to the reactor. After 5 minutes, a sample of 5 ml liquid is removed from the autoclave. The process of feeding and sampling is repeated for another 5 cycles in order to approximate the conditions in a continuous flow stirred tank reactor. The reactor was then cooled to room temperature in 15 minutes, depres surized, opened, and the reactor content was filtered. 30 ml of reactor liquid with an average initial concentration of 12%w glucose is obtained. In addition, 30 ml combined sample liquid with an average initial concentration of 8%wt glucose is obtained. Yields of MEG, MPG and 1, 2-butanediol (1,2- BDO) were quantified by GC-FID, applying a CPSil-5 column and can be seen in Table 1.

Reference： [1]Patent: WO2016/1169,2016,A1 .Location in patent: Page/Page column 12; 13; 14
[2]Patent: WO2015/28398,2015,A1 .Location in patent: Page/Page column 12; 13

44
[ 492-62-6 ]
[ 57-55-6 ]
[ 107-21-1 ]

Yield	Reaction Conditions	Operation in experiment
15.44%; 10.24%	With sodium tungstate; 5 wt% ruthenium/carbon; hydrogen; In water; at 220℃; under 62256.2 Torr; for 2h;Sealed tube;	A feed comprising 20% dextrose by weight in water was reacted in a high throughput screening batch reactor. The catalytic reaction conditions were carried out in sealed hydrogenolysis reactors at 220 degrees Celsius, at 8.3 MPa (1200 psi) hydrogen pressure for a 2 hour hold period. Products of the reaction were analyzed by gas chromatography (?GC?), which showed lower ethylene glycol selectivity with greater selectivity for propylene glycol using co-catalysts comprising Mo, in the form of potassium molybdate (K2M0O4) with 5% Ru CP, as compared to sodium tungstate (Na2W04) with 5% Ru CP (with the exception of 5K2M0O4 versus 5Na2W04 and I OK2M0O4 versus l0Na2WO4 as to PG selectivity). [58] The GC results also show lower ethylene glycol selectivity with greater selectivity for propylene glycol using co-catalysts comprising Mo, in the form of potassium molybdate (K2M0O4) with 5% Ru CP as compared to ammonium metavanadate (NH4VO3) with 5% Ru CP. [59] Results using various reactor co-catalysts are shown in Table 7-9 below, with 100% dextrose conversion, and without glycerol detected for the runs shown in Tables 7-9.
		Example 1 30 ml deionized water, 0.300 g of a catalyst consisting of W (10.88) -Ni (3.63) -Pt (0.05) and Zr02 and 0.300 g of a catalyst consisting of Ru(1.0%) on Si02 catalyst were charged into a 60 ml autoclave equipped with a gas stirrer and hydrogen supply. The autoclave was closed, the gas phase was replaced by nitrogen, then by hydrogen and the autoclave was pressurised to 30 bara pressure. The autoclave was stirred at 1450 rpm, heated to 195 C in 15 minutes and pressurised with hydrogen to 75 bara pressure. 5 ml of a solution of 20%wt glucose in water was fed to the reactor. After 5 minutes, a sample of 5 ml liquid is removed from the autoclave. The process of feeding and sampling is repeated for another 5 cycles in order to approximate the conditions in a continuous flow stirred tank reactor. The reactor was then cooled to room temperature in 15 minutes, depres surized, opened, and the reactor content was filtered. 30 ml of reactor liquid with an average initial concentration of 12%w glucose is obtained. In addition, 30 ml combined sample liquid with an average initial concentration of 8%wt glucose is obtained. Yields of MEG, MPG and 1, 2-butanediol (1,2- BDO) were quantified by GC-FID, applying a CPSil-5 column and can be seen in Table 1. Example 2 The reactor liquid (30ml) from Example 1 and 0.300g of a Ru(1.0)/SiO2 catalyst were charged into a 60 ml autoclave equipped with a gas stirrer and hydrogen supply. The autoclave was closed, and the gas phase was replaced by nitrogen, then by hydrogen. The autoclave was then pressurized to 30 bara. The autoclave was stirred at 1450 rpm, heated to 195C in 15 minutes, pressurised to 85 bara and kept at reaction conditions for 75 minutes. Such conditions are representative of a plug flow reactor. The reactor was then cooled down to room temperature in 15 minutes, depres surised, opened and a liquid sample was taken for analysis . Yields of MEG, MPG and 1 , 2-butanediol (1, 2-BDO) have been quantified by GC-FID, applying a CPSil-5 column. Yields are shown in Table 2.

Reference： [1]Patent: WO2019/156854,2019,A1 .Location in patent: Paragraph 56-73
[2]Patent: WO2015/28398,2015,A1 .Location in patent: Page/Page column 12; 13; 14

45
[ 492-62-6 ]
[ 57-55-6 ]
[ 107-21-1 ]
[ 584-03-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: alpha-D-glucopyranose With 1% Ru/SiO2; hydrogen In water at 195℃; Inert atmosphere; Stage #2: With 1% Ru/SiO2; hydrogen In water at 195℃; for 1.25h; Inert atmosphere;	1; 3 Example 1; Example 3 Example 1 30 ml deionized water, 0.300 g of a catalyst consisting of W (10.88) -Ni (3.63) -Pt (0.05) and Zr02 and 0.300 g of a catalyst consisting of Ru(1.0%) on Si02 catalyst were charged into a 60 ml autoclave equipped with a gas stirrer and hydrogen supply. The autoclave was closed, the gas phase was replaced by nitrogen, then by hydrogen and the autoclave was pressurised to 30 bara pressure. The autoclave was stirred at 1450 rpm, heated to 195° C in 15 minutes and pressurised with hydrogen to 75 bara pressure. 5 ml of a solution of 20%wt glucose in water was fed to the reactor. After 5 minutes, a sample of 5 ml liquid is removed from the autoclave. The process of feeding and sampling is repeated for another 5 cycles in order to approximate the conditions in a continuous flow stirred tank reactor. The reactor was then cooled to room temperature in 15 minutes, depres surized, opened, and the reactor content was filtered. 30 ml of reactor liquid with an average initial concentration of 12%w glucose is obtained. In addition, 30 ml combined sample liquid with an average initial concentration of 8%wt glucose is obtained. Yields of MEG, MPG and 1, 2-butanediol (1,2- BDO) were quantified by GC-FID, applying a CPSil-5 column and can be seen in Table 1. Example 3 The filtered combined sample liquid (30ml) from Example 1 and 0.200g of a Ru(1.0)/SiO2 catalyst were charged into a 60 ml autoclave equipped with a gas stirrer and hydrogen supply. The autoclave was closed, and the gas phase was replaced by nitrogen, then by hydrogen. The autoclave was pressurized to 30 bara. The autoclave was stirred at 1450 rpm, heated to 195°C in 15 minutes, pressurised to 85 bara and kept at reaction conditions for 75 minutes. The reactor was then cooled to room temperature in 15 minutes, depressurised, opened and a liquid sample was taken for analysis. Yields of MEG, MPG and 1 , 2-butanediol (1, 2-BDO) have been quantified by GC-FID, applying a CPSil-5 column. Yields are shown in Table 2.

Reference： [1]Current Patent Assignee: SHELL PLC - WO2015/28398, 2015, A1 Location in patent: Page/Page column 12; 13; 14

46
[ 492-62-6 ]
[ 67-47-0 ]
[ 7425-74-3 ]
[ 498-07-7 ]

Yield	Reaction Conditions	Operation in experiment
21%	With Na₂ZrSi₄O₁₁ In dimethyl sulfoxide at 160℃; for 1h; Autoclave;
7%	With Na₂ZrSi₄O₁₁ In dimethyl sulfoxide at 160℃; for 0.5h; Autoclave;

Reference： [1]Yue, Chaochao; Rigutto, Marcello S.; Hensen, Emiel J. M. [Catalysis Letters, 2014, vol. 144, # 12, p. 2121 - 2128]
[2]Yue, Chaochao; Rigutto, Marcello S.; Hensen, Emiel J. M. [Catalysis Letters, 2014, vol. 144, # 12, p. 2121 - 2128]

47
[ 492-62-6 ]
[ 5736-88-9 ]
C₁₇H₂₄O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With toluene-4-sulfonic acid; orthoformic acid triethyl ester; In N,N-dimethyl-formamide; at 20℃; for 5h;Inert atmosphere;	Synthesis of compound [G3?]Under a nitrogen atmosphere, to a solution of D (+)-glucose (1.8 g, 10 mmol) in DMF (7 mL), 4-butoxybenzaldehyde [G10] (1.9 g, 10 mmol) and p-toluenesulfonic acid (54 mg, 0.3 mmol) were added, and the mixed solution was stirred at room temperature for 10 minutes. To the mixed solution, triethyl orthoformate (1.5 g, 10 mmol) was added dropwise at room temperature. After the dropwise addition, the mixed solution was stirred at room temperature for 20 minutes and stirred under reduced pressure at room temperature for 5 hours. To the reaction solution, a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated salt solution and then was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the obtained solid was washed with hexane. The product was purified by column chromatography (silica gel, chloroform: methanol=10:0 to 9:1 (v/v)), yielding a white solid. An HPLC chart and 1H NMR (500 MHz) of the product after purification are shown in FIG. 1 and FIG. 2, respectively. The HPLC observation indicates two components (retention time: 2.16 minutes and 2.31 minutes (solvent: acetonitrile/water=50/50)), and the 1H NMR also suggests two components. However, LC-MS observation shows a molecule ion peak (EST-MS cald for C17H25O7 [M+H]+341, found 341) of the target compound. Consequently, the target compound was obtained as a mixture of alpha-form and beta-form: Yield 32%.

Reference： [1]Patent: US2015/25157,2015,A1 .Location in patent: Paragraph 0209; 0210; 0211; 0212

Yield	Reaction Conditions	Operation in experiment
		Glucose detection was carried out as follows: firstly, 100 muL of GOx aqueous solution (1.0 mg mL-1) and 100 muL of D-glucose with various concentration were mixed in 500 muL of NaH2PO4 buffer (0.5 mM, pH 7.0) and incubated at 37C for 1 h; then 200 muL of TMB (5 mM, ethanol solution), 100 muL of the RGO-INs stock solution (1 mg mL-1) and 4.00 mL of NaAc buffer (0.2 M, pH 3.0) were successively added to the glucose reaction solution; finally, the mixed solution was incubated at 40C for 30 min for standard curve measurement.

49
[ 492-62-6 ]
[ 57-48-7 ]
[ 526-95-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 84% 2: 7%	With dihydrogen peroxide; iron(II) sulfate In water at 70℃; for 0.25h; Green chemistry;

Reference： [1]Rinsant, Damien; Chatel, Gregory; Jrme, Franois [ChemCatChem, 2014, vol. 6, # 12, p. 3355 - 3359]

50
[ 492-62-6 ]
[ 67-47-0 ]
[ 123-76-2 ]

Yield	Reaction Conditions	Operation in experiment
	With niobium-modified Beta-zeolites; In water; at 180℃; for 12h;	The activity tests in the batch mode were carried out as follows:0.03 g of catalyst were added to a solution of 0.18 g (1 mmole) glucosein 5 mL water. After closing, the reactor was heated up to 180 C, understirring (1200 rpm), for 12-24 h. Additional catalytic tests were made inthe same conditions but in a biphasic solvent (3.5 mL aqueous solutionof 20% NaCl and 1.5 mL MIBK). To investigate the chemical stability ofthe catalysts, the content of the leached metal (ie, Nb and/or Al) intothe reaction liquid, was determined by ICP-OES (Agilent Technologies,700 Series). Another catalytic test has been carried out with the samescope: 0.03 g Nb-Beta zeolite catalyst was boiled in 5 mL water, at180 C, for 3 h, under stirring. After 3 h, the catalyst was separated fromthe liquid by centrifugation, and washed and dried at room temperature,then used in the reaction test in the following conditions: 0.18 g (1mmole) glucose in 5 mL water, 180 C and 24 h.

Reference： [1]ChemCatChem,2017,vol. 9,p. 2739 - 2746
[2]Chemistry - A European Journal,2014,vol. 20,p. 12298 - 12309
[3]New Journal of Chemistry,2016,vol. 40,p. 7958 - 7967
[4]Catalysis Today,2019,vol. 325,p. 109 - 116

51
[ 498-07-7 ]
[ 492-62-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sulfuric acid In water at 110℃; for 24h;

Reference： [1]Santhanaraj, Daniel; Rover, Marjorie R.; Resasco, Daniel E.; Brown, Robert C.; Crossley, Steven [ChemSusChem, 2014, vol. 7, # 11, p. 3132 - 3137]

52
[ 492-62-6 ]
[ 57-55-6 ]
[ 50-70-4 ]
[ 107-21-1 ]
[ 56-81-5 ]
[ 584-03-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In water at 180℃;	Catalytic reaction process General procedure: Hydrogenolysis of glucose was performed in a vertical fixed-bed reactor (i.d. 12 mm, length 600 mm) with a cold trap. Prior to the test, 2.0 g catalyst (20-40 mesh) was loaded at the isothermal zone and in situ reduced at 250 °C for 2 h in hydrogen (100 mL/min). After reduction, a 5 wt% aqueous glucose solution was pumped into the reactor, and mixed with H2 co-feeding. The liquid products were collected in a gas-liquid separator immersed in an ice-water trap. Typical reaction conditions were as follows: 4 MPa H2 (45 mL/min), 5 wt% aqueous glucose solution, aqueous glucose solution flow rates were set as 24, 19.2, and 14.4 mL/h, which can be shown as 0.6, 0.48, and 0.36 h-1 in WHSV (weight hourly space velocity).

Reference： [1]Liu, Chengwei; Zhang, Chenghua; Zhu, Yulei; Li, Yongwang; Hao, Shunli; Sun, Sikai; Liu, Kangkai; Xu, Jian [Catalysis Today, 2016, vol. 261, p. 116 - 127]

53
[ 123-75-1 ]
[ 492-62-6 ]
1-[2,3,4,5,6-pentahydroxyhexyl]pyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With hydrogen; In methanol; at 60℃; under 30402 - 38002.6 Torr;Autoclave;	To a vigorously stirred mixture of 60 mL methanol and 18 mL of pyrrolidine, 20 g of anhydrous glucose were added and heated until complete dissolution was reached (50 , 20 min). Then,the solution was placed into a stainless steel autoclave, and 5 g of Ni-Raney were added. Hydrogenation was carried out with stirring until the full absorption of stoichiometric amount of hydrogen (pressure of hydrogen 40-50 atm, 60 , 4-6 h). Catalysts was filtered, methanol was removed on a rotor evaporator and the reaction product was dried in vacuo (60-70 ), then twice recrystallized from isopropanol (100 mL). Yield 68 %. 1H NMR (D2O), delta: 1.71 (m, 4 H); 2.5-2.68 (m, 6 H); 3.52-3.64 (m, 2 H); 3.64-3.8 (m, 3 H); 3.87 (q, 1 H).

Reference： [1]Russian Chemical Bulletin,2015,vol. 64,p. 2811 - 2815
Izv. Akad. Nauk, Ser. Khim.,2015,p. 2811 - 2815,5

54
[ 492-62-6 ]
[ 100-46-9 ]
(3R,4S,5S,6R)-2-(benzylamino)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With acetic acid; In ethanol; water; at 4℃; for 1h;Inert atmosphere;	1:1(v:v)EtOH andH2 O (2mL)to the D-beta-glucose (beta-D-glucose, 1.0 g, 5.55 mmol, 1 equiv), benzylamine (benzyl amine, 0.8 mL, 7.22 mmol , 1.3 equiv), and the AcOH (7 mg, 0.11 mmol, 0.02 equiv) was added the mixture was stirred at 4 for 1 hour.The mixture was concentrated under reduced pressure and purifying the product are not silica gel flash column chromatography (eluent CH2Cl2and12:1MeOH) to give a1a(1.4 g, 5.20 mmol) was obtained (yield 93%, white solid ).

Reference： [1]Patent: KR2016/35931,2016,A .Location in patent: Paragraph 0081-0084

55
[ 71-23-8 ]
[ 492-62-6 ]
[ 645-67-0 ]

Yield	Reaction Conditions	Operation in experiment
	With SBA-15-SO3H; tin-containing molecular sieve; In water; at 170℃; for 7h;High pressure;	A mixture of 1 part of α-glucose, 20 parts of n-propanol, 0.1 part of SBA-15-SO3H and 0.1 g of Sn-Beta was mixed and placed in a hydrothermal reactor and heated at 170C for 7 hours. After cooling, The yield of propyl levulinate was 35 mol%.

Reference： [1]Patent: CN103408422,2016,B .Location in patent: Paragraph 0043; 0044

56
[ 492-62-6 ]
[ 71-36-3 ]
[ 2052-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	With SBA-15-SO3H; tin-containing molecular sieve; In water; at 170℃; for 7h;High pressure;	A mixture of 1 part of alpha-glucose, 20 parts of n-butanol, 0.1 part of SBA-15-SO3Hand 0.1 g of Sn-Beta was mixed and placed in a hydrothermal reactor and heated at 170 C for 7 hours. After cooling, The yield of the butyl levulinate was 30 mol%.

Reference： [1]Patent: CN103408422,2016,B .Location in patent: Paragraph 0045; 0046

57
[ 492-62-6 ]
[ 64-17-5 ]
[ 67-47-0 ]
[ 1917-65-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 13 %Chromat. 2: 7 %Chromat.	With sulfo modified MIL-101Cr In tetrahydrofuran; water at 130℃; for 24h;
1: 11 %Chromat. 2: 5 %Chromat.	With sulfo modified MIL-101Cr In water at 130℃; for 24h;

Reference： [1]Herbst, Annika; Janiak, Christoph [New Journal of Chemistry, 2016, vol. 40, # 9, p. 7958 - 7967]
[2]Herbst, Annika; Janiak, Christoph [New Journal of Chemistry, 2016, vol. 40, # 9, p. 7958 - 7967]

58
[ 492-62-6 ]
[ 108-24-7 ]
[ 4163-60-4 ]

Yield	Reaction Conditions	Operation in experiment
92.5%	With sodium acetate; at 100 - 130℃; under 760.051 Torr; for 4h;Large scale;	acetic anhydride 2000 kg,Sodium acetate 40kg added to 5000L jacketed reactor,Then add 616 kg of glucose twice,Atmospheric pressure 100 ~ 130 insulation 4h,After completion of the reaction, the mixture was distilled under reduced pressure at 95 C / -0.080 MPa,Recycle acetic acid and acetic anhydride.After cooling, the ethanol was added to the concentrated product, and the material was introduced into the crystallization kettle. The mother liquor was introduced into the beta-pentaacetylglucose seed crystal and the cooling rate was controlled. The crystals were crystallized at 10 to 35 C for 24 h and centrifuged. The filter cake was washed with deionized water Twice after drying 12h, get beta-pentaacetyl glucose, the yield of 92.5%. The mother liquor is distilled to recover ethanol.

Reference： [1]Patent: CN105968149,2016,A .Location in patent: Paragraph 0023; 0024; 0028; 0029; 0033; 0034

59
[ 492-62-6 ]
[ 497-76-7 ]

Reference： [1]Patent: CN105968149,2016,A

60
medalose [ No CAS ]
[ 14131-68-1 ]
[ 492-61-5 ]
[ 492-62-6 ]
[ 7296-64-2 ]
[ 709-50-2 ]
[ 97-30-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid In 1,4-dioxane at 50℃; for 22h;	2.5.1 Methylglycosidation/acid hydrolysis of Medalose Medalose (15mg) was ref1uxed with absolute MeOH (2ml) at 70°C for 18h in the presence of cation exchange R-l20 (H) resin. The reaction mixture was filtered while hot and filtrate was concentrated. To a solution of methylglycoside of Medalose in 1,4-dioxane (I ml), 0.1NH2S04 (1ml) was added and the solution was warmed for 30min at 50°C. The hydrolysis was complete after 22h. The hydrolysate was neutralized with freshly prepared BaCO3 filtered and concentrated under reduced pressure to afford α-and β-methylglucosides along with the GIc, Gal and GlcNAc. Their identification was confirmed by comparison with authentic samples (TLC, PC).

Reference： [1]Gangwar, Lata; Singh, Rinku; Deepak, Desh [Journal of Molecular Structure, 2018, vol. 1153, p. 157 - 161]

61
[ 492-62-6 ]
[ 77-76-9 ]
[ 160651-67-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With sulfuric acid; In acetone; at 20℃; for 1.5h;	glucose (1.8 g, 10 mmol) dissolved in 20 ml of acetone, then adding 1, 1 - dimethoxy propane (2.1 g, 20 mmol) and sulfuric acid (1 drop), stirring at room temperature for 1 hour, concentrated to do, ethyl acetate to dissolve the residue, in order to water washing, drying of the organic layer concentrated, to obtain 2 . 13 g colorless oil of, yield 82%.

Reference： [1]Patent: CN107857789,2018,A .Location in patent: Paragraph 0138

62
[ 492-62-6 ]
[ 761423-87-4 ]

Reference： [1]Patent: CN108276396,2018,A

63
[ 492-62-6 ]
[ 4301-04-6 ]
1,2,3,4,6-O-pentakis(2,2-dichloromethylpropanoyl)-α-D-glucopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88.3%	With pyridine; dmap; In dichloromethane; at 0 - 20℃; for 20.5h;Inert atmosphere;	D-glucose (XII-1, 5 g, 27.8 mmol) was suspended in anhydrous dichloromethane (80 mL) under nitrogen and the mixture was stirred at room temperature for 5 min then cooled to 0 C and stirred for 10 min.Then, pyridine (30 mL) was added dropwise to the resulting mixture over about 10-15 minutes with stirring, and N,N-dimethylaminopyridine (0.25 g, 2.04 mmol) was added.The temperature was lowered to 0 C, and a solution of 2,2-dichloromethylpropionyl chloride (XII-7) in dichloromethane (23.6 g of acid chloride (152.9 mmol) dissolved in 15 mL of dichloromethane) was slowly added dropwise to the reaction solution. Add 30 minutes.After the dropwise addition was completed, the ice bath was removed, and the resulting mixture was stirred at room temperature for 20 hours.The resulting mixture was then poured into dichloromethane (100 mL) and hydrochloric acid (1.5 M, 75 mL).In the resulting mixture, the resulting two phases were separated.The organic layer was washed with aq. sodium bicarbonate (100 mL).Ethanol (95%, 50 mL) was added to the obtained residue, and the mixture was heated to reflux.The mixture was refluxed for 1 hour, and the temperature was slowly lowered to 0 C (the cooling time was about 30 minutes), and the crystallization was stirred for 2 hours.Filtration, washing the filter cake with 95% ethanol, and drying under vacuum at room temperature overnight to obtain the desired product intermediate XII-8; that is, 1,2,3,4,6-O-penta(2,2-dichloromethylpropanoyl) -D-glucopyranose. Yield 88.3%;

Reference： [1]Patent: CN109111490,2019,A .Location in patent: Paragraph 0134; 0135; 0136; 0137; 0138

64
[ 492-62-6 ]
[ 50547-79-0 ]
1,2,3,4,6-O-pentakis(3-chloro-2,2-dichloromethylpropanoyl)-α-D-glucopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With pyridine; dmap; In dichloromethane; at 0 - 20℃; for 20.5h;Inert atmosphere;	D-glucose (XII-1, 28.0 mmol) was suspended in anhydrous dichloromethane (80 mL) under nitrogen and the mixture was stirred at room temperature for 5 min then cooled to 0 C and stirred for 10 min.Then, to the resulting mixture, pyridine (30 mL) was added dropwise with stirring for about 10-15 minutes, and N,N-dimethylaminopyridine (2.04 mmol) was added.The temperature was lowered to 0 C, and a solution of 3-chloro-2,2-dichloromethylpropionyl chloride (XII-11) in dichloromethane was slowly added dropwise to the reaction solution.(Acyl chloride 152.9 mmol was dissolved in 15 mL of dichloromethane) and added dropwise for 30 minutes.After the dropwise addition was completed, the ice bath was removed, and the resulting mixture was stirred at room temperature for 20 hours.Then, the resulting mixture was poured into a mixed solution of dichloromethane (100 mL) and hydrochloric acid (1.5 M, 75 mL), and the obtained two phases were separated.The organic layer was washed with aq. sodium bicarbonate (100 mL).Ethanol (95%, 50 mL) was added to the obtained residue, and the mixture was heated to reflux. The mixture was refluxed for 1 hour, and the temperature was gradually lowered (the cooling time was about 30 minutes) to 0 C, and the crystallization was stirred for 2 hours.Filtration, washing the filter cake with 95% ethanol, and drying under vacuum at room temperature overnight to obtain the target product intermediate XII-12;1,2,3,4,6-O-penta(3-chloro-2,2-dichloromethylpropanoyl)-D-glucopyranose. Yield 88%;

Reference： [1]Patent: CN109111490,2019,A .Location in patent: Paragraph 0170; 0171; 0173; 0174; 0175

65
[ 492-62-6 ]
[ 4300-97-4 ]
C₃₁H₄₇Cl₅O₁₁ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87.5%	With pyridine; dmap; In dichloromethane; at 0 - 20℃; for 20.5h;Inert atmosphere;	D-glucose (XII-1, 5 g, 27.8 mmol) was suspended in anhydrous dichloromethane (80 mL) under nitrogen and the mixture was stirred at room temperature for 5 min then cooled to 0 C and stirred for 10 min. Then, to the resulting mixture, pyridine (30 mL) was added dropwise with stirring for about 10-15 minutes, and N,N-dimethylaminopyridine (0.25 g, 2.04 mmol) was added. The temperature was lowered to 0 C, and a dichloromethane solution of monochloropivaloyl chloride (monochloropivaloyl chloride (XII-2, 23.6 g, 152.9 mmol) dissolved in 15 mL of dichloromethane) was slowly added dropwise to the reaction mixture. Add the time for 30 minutes. After the dropwise addition was completed, the ice bath was removed, and the resulting mixture was stirred at room temperature for 20 hours. The resulting mixture was then poured into dichloromethane (100 mL) and hydrochloric acid (1.5 M,In the resulting mixture of 75 mL), the resulting two phases were separated. The organic layer was washed with sodium bicarbonate solution (100 mL) and organic layer reducedConcentrate to near dryness. Ethanol (95%, 50 mL) was added to the obtained residue, and the mixture was heated to reflux. returnThe flow was kept for 1 hour, and the temperature was gradually lowered (the cooling time was about 30 minutes) to 0 C, and the crystallization was stirred for 2 hours. Filtered, 95%The filter cake was washed with ethanol and dried under vacuum at room temperature overnight to give the desired product intermediate XII-3; i.e., 1,2,3,4,6-O-pentachloropivaloyl-D-glucopyranose. Yield 87.5%;

Reference： [1]Patent: CN109111490,2019,A .Location in patent: Paragraph 0090; 0092; 0094; 0095; 0096

66
[ 492-62-6 ]
[ 110-13-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	With hydrogenchloride; 5%-palladium/activated carbon; hydrogen; In chloroform; water; at 100℃; under 45004.5 Torr; for 2h;	Willow, pine, mulberry, birch, newspaper, cotton, cotton, cotton, etc. are pulverized and dried. 20 g is added to a 4 L reactor, 2 g of 5% Pd/C is added, 0.4 L of 36% aqueous hydrochloric acid and 1.2 are added. L-chloroform was charged with 6 MPa of hydrogen and reacted at 100 C for 2 hours.Table 1 Preparation of 2,5-hexanedione from different raw materials

Reference： [1]Patent: CN109896938,2019,A .Location in patent: Paragraph 0023-0026

67
[ 492-62-6 ]
[ 57-55-6 ]

Yield	Reaction Conditions	Operation in experiment
15.45%	With potassium molybdate(VI); 5 wt% ruthenium/carbon; hydrogen; In water; at 220℃; under 62256.2 Torr; for 2h;Sealed tube;	A feed comprising 20% dextrose by weight in water was reacted in a high throughput screening batch reactor. The catalytic reaction conditions were carried out in sealed hydrogenolysis reactors at 220 degrees Celsius, at 8.3 MPa (1200 psi) hydrogen pressure for a 2 hour hold period. Products of the reaction were analyzed by gas chromatography (?GC?), which showed lower ethylene glycol selectivity with greater selectivity for propylene glycol using co-catalysts comprising Mo, in the form of potassium molybdate (K2M0O4) with 5% Ru CP, as compared to sodium tungstate (Na2W04) with 5% Ru CP (with the exception of 5K2M0O4 versus 5Na2W04 and I OK2M0O4 versus l0Na2WO4 as to PG selectivity). [58] The GC results also show lower ethylene glycol selectivity with greater selectivity for propylene glycol using co-catalysts comprising Mo, in the form of potassium molybdate (K2M0O4) with 5% Ru CP as compared to ammonium metavanadate (NH4VO3) with 5% Ru CP. [59] Results using various reactor co-catalysts are shown in Table 7-9 below, with 100% dextrose conversion, and without glycerol detected for the runs shown in Tables 7-9.

Reference： [1]Patent: WO2019/156854,2019,A1 .Location in patent: Paragraph 56-73

68
[ 492-62-6 ]
[ 632-46-2 ]
1-O-(2,6-dimethylbenzoyl)-β-D-glucopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With di-isopropyl azodicarboxylate; triphenylphosphine In 1,4-dioxane at 20℃; for 0.5h; Inert atmosphere; stereoselective reaction;

Reference： [1]Fujimori, Yusuke; Furuta, Takumi; Kawabata, Takeo; Nagaishi, Masaru; Sasamori, Takahiro; Shibayama, Hiromitsu; Takeuchi, Hironori; Tokitoh, Norihiro; Ueda, Yoshihiro; Yoshimura, Tomoyuki [Organic Letters, 2020]

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