[ CAS No. 57817-89-7 ] {[proInfo.proName]}

Name: 57817-89-7|(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl (4R,4aS,6aR,9S,11aR,11bS)-9-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-4,11b-dimethyl-8-methylenetetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate|95%
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Quality Control of [ 57817-89-7 ]

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Product Details of [ 57817-89-7 ]

CAS No. :	57817-89-7	MDL No. :	MFCD00079561
Formula :	C₃₈H₆₀O₁₈	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	804.87	Pubchem ID :	-
Synonyms :

Safety of [ 57817-89-7 ]

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 [ 57817-89-7 ]

* 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 [ 57817-89-7 ]
Downstream synthetic route of [ 57817-89-7 ]

[ 57817-89-7 ] Synthesis Path-Upstream 1~12

1
[ 133-89-1 ]
[ 64849-39-4 ]
[ 57817-89-7 ]

Reference： [1] Patent: WO2014/193888, 2014, A1, . Location in patent: Page/Page column 56
[2] Patent: WO2016/43926, 2016, A1, . Location in patent: Page/Page column 56
[3] Patent: WO2016/120486, 2016, A1, . Location in patent: Paragraph 00196

2
[ 40878-59-9 ]
[ 57817-89-7 ]

Reference： [1] Tetrahedron, 1980, vol. 36, p. 2641 - 2648

3
[ 572-09-8 ]
[ 57817-89-7 ]

Reference： [1] Tetrahedron, 1980, vol. 36, p. 2641 - 2648

4
[ 66335-80-6 ]
[ 66537-21-1 ]
[ 57817-89-7 ]

Reference： [1] Tetrahedron, 1980, vol. 36, p. 2641 - 2648

5
[ 57-50-1 ]
[ 57817-89-7 ]

Reference： [1] Patent: WO2016/43926, 2016, A1,

6
[ 57817-89-7 ]
[ 27975-19-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sulfuric acid In water	Ent-16-oxobeyeran-19-oic acid was synthesized by hydrolysis of stevioside with 10percent sulfuric acid [48] . Yield 93percent; Mp 228.4-230.8 °C; IR (KBr): 3448, 2955, 2924, 2848, 1736, 1692, 1453, 1404, 1373, 1320, 1268, 1214, 1180, 1150, 1108, 973, 950, 796, 589 cm^-1; ¹H NMR (400 MHz, CDCl_3, ppm): δ 2.64 (dd, J = 18.64, 3.76 Hz, 1H), 2.17 (d, J = 13.40 Hz, 1H), 1.90-1.37 (m, 13H), 1.25 (s, 3H), 1.22-1.14 (m, 3H), 1.06-1.03 (m, 1H), 0.98 (s, 3H), 0.95-0.88 (m, 1H), 0.78 (s, 3H); ¹³C NMR (100 MHz, CDCl_3, ppm): δ 224.22, 184.33, 56.79, 57.62, 56.09, 54.83, 49.73, 49.59, 44.38, 42.02, 40.42, 40.42, 38.99, 38.34, 32.80, 29.69, 22.32, 20.57, 19.55, 14.04; HRMS (ESI, m/z) calcd for C₂₀H₃₀O₃Na [M + Na]⁺ 341.2093. Found: 341.2085.

Reference： [1] Chemistry and Biodiversity, 2013, vol. 10, # 2, p. 177 - 188
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 19, p. 2485 - 2490
[3] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 26 - 40
[4] Journal of Chemical Crystallography, 2009, vol. 39, # 2, p. 108 - 111
[5] Journal of Chemical Crystallography, 2011, vol. 41, # 4, p. 519 - 522
[6] Journal of Natural Products, 2002, vol. 65, # 3, p. 273 - 277
[7] Life Sciences, 2005, vol. 77, # 17, p. 2127 - 2140
[8] Journal of the American Chemical Society, 2007, vol. 129, # 41, p. 12453 - 12460
[9] Patent: EP1757282, 2007, A1, . Location in patent: Page/Page column 10
[10] Planta Medica, 2008, vol. 74, # 8, p. 816 - 821
[11] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 4, p. 1464 - 1473
[12] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 70 - 82
[13] Life Sciences, 2014, vol. 116, # 1, p. 31 - 36
[14] Food Chemistry, 2016, vol. 190, p. 270 - 275
[15] Patent: CN108456240, 2018, A, . Location in patent: Paragraph 0063-0065

7
[ 57817-89-7 ]
[ 27975-19-5 ]

Reference： [1] Phytochemistry, 1996, vol. 43, # 2, p. 393 - 395
[2] Journal of Natural Products, 2004, vol. 67, # 3, p. 407 - 410
[3] Patent: US9314438, 2016, B2, . Location in patent: Page/Page column 26; 27

8
[ 50-99-7 ]
[ 7664-93-9 ]
[ 57817-89-7 ]
[ 27975-19-5 ]

Reference： [1] Journal de Pharmacie et de Chimie, 1931, vol. <8> 14, p. 99,100[2] Bulletin de la Societe de Chimie Biologique, 1931, vol. 13, p. 636,645, 656

9
[ 57817-89-7 ]
[ 57-50-1 ]
[ 58543-16-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With Arabidopsis thaliana sucrose synthase gene; UDP-glucosyltransferase from Stevia rebaudiana, recombinant; magnesium chloride In aq. phosphate buffer at 30℃; for 30 h; Enzymatic reaction	After pEUGT-SUS expressionin E. coli, the cells were harvested and washed twice in potassium phosphate buffer (100 mM, pH 7.2). A lysate containing soluble proteins was obtained by sonication on an ice-water bath and subsequent clarification by centrifugation at 4 °C. The supernatant was used as the crude extract. Total protein concentrations were measured by the Bradford assay using bovine serum albumin (BSA) as a standard.23) The substratestevioside was incubated with aliquots of the crude extract at 30 °C in a reaction mixture containing varying concentrations of UDP-glucose or UDP, sucrose, and 3 mM MgCl2 in potassium phosphate buffer (100 mM, pH 7.2) for synthesis of rebaudioside A.

Reference： [1] Bioscience, Biotechnology and Biochemistry, 2016, vol. 80, # 1, p. 67 - 73

10
[ 57817-89-7 ]
[ 58543-16-1 ]

Yield	Reaction Conditions	Operation in experiment
150 mg	With β-1,3-glucanase from Irpex lacteus In aq. buffer at 55℃; for 3 h; Enzymatic reaction	Stevioside (200 mg) and curdlan (400 mg) was dissolved in citrate buffer (0.1 M with pH 4.5) and β-1,3-glucanase 3.425 U/g was added. The reaction mixture was shaking in an incubator for 3 hr at 55 °C. The reaction mixture was cooled to room temperature and the enzyme was deactivated by boiling at 100 °C. Progress of the reaction was monitored by TLC using solvent system ethyl acetate/ethanol/H2O (8:2:1.2, v/v/v) (Jaitak et al., 2009a,b). The developed plate was dried and spots were visualized by spraying with 5percent sulfuric acid. Reaction mixture was passed through the Dianion HP-20, followed by washing with methanol. Methanol fraction was dried over rota vapor and recrystallized using cold ethanol to yield 150 mg of pure Rebaudioside A. Product was confirmed by, NMR, HRMS and melting point determination. Rebaudioside A: MP 245–247 °C, Rf value 0.45, ethyl acetate:ethanol:water (8:2:1.2, v/v/v), 1H NMR (400 MHz, DMSO): 5.64 (1H, d, J = 8 Hz), 5.28 (1H, d, J = 8 Hz), 5.02 (1H, t, J = 8 Hz) and 4.95 (1H, d, J = 8 Hz). 13C-NMR (100 MHz, DMSO): δc 14.89, 18.56, 19.79, 21.14, 28.04, 37.48, 38.70, 39.20, 40.03, 41.04, 41.64, 43.10, 43.20, 47.0, 53.23, 56.52, 60.56, 61.02, 61.34, 68.90, 69.48, 70.01, 70.32, 72.44, 73.59, 74.35, 75.98, 76.49, 76.88, 76.98, 77.42, 78.46, 78.79, 78.88, 79.12, 85.40, 86.27, 94.45, 96.45, 102.47, 102.98, 104.0, 152.78, 175.63. HRMS (ESI): m/z calc.for C44H70O23 [M-H]: 965.4230; found 965.5040.

Reference： [1] Phytochemistry, 2016, vol. 125, p. 106 - 111

11
[ 952585-00-1 ]
[ 57817-89-7 ]
[ 58543-16-1 ]

Reference： [1] Bioscience, Biotechnology and Biochemistry, 2016, vol. 80, # 1, p. 67 - 73

12
[ 133-89-1 ]
[ 57817-89-7 ]
[ 58543-16-1 ]

Reference： [1] Patent: WO2014/193888, 2014, A1, . Location in patent: Page/Page column 9; 46-47; 52-53
[2] Patent: WO2016/43926, 2016, A1, . Location in patent: Page/Page column 47

[ 57817-89-7 ] Synthesis Path-Downstream 1~9

1
[ 57817-89-7 ]
[ 471-80-7 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: stevioside With sodium periodate; hydrogen In water at 20℃; for 16h; Stage #2: With potassium hydroxide In water at 0℃; for 1h; Reflux;
70%	With sodium periodate; water; potassium hydroxide
60%	Stage #1: stevioside With sodium periodate In water at 25℃; for 16h; Stage #2: With water; potassium hydroxide at 100℃; for 2h;

26%	Stage #1: stevioside With sodium periodate In water at 20℃; for 16h; Stage #2: With potassium hydroxide for 1h; Reflux;
8%	Stage #1: stevioside With sodium periodate In water Stage #2: With potassium hydroxide at 110℃; for 1h;
	With potassium hydroxide; sodium periodate 1.) H₂O, RT, 16 h, 2.) reflux, 1 h; Yield given. Multistep reaction;
		Compound B (ent-13-hydroxykaur-16-en-18-oic acid) is produced from stevioside through a series processes including oxidation, hydrolysis, acidification, extraction, purification and crystallization. The structure of compound B is confirmed by inferred analysis and NMR, which are consistence with previously published data. (Mosettig E. et al.,1963). The purity of compound B is greater than 99% as determined by high performance liquid chromatograph.
3.2 g	With pectinase A; water In toluene at 50℃; for 336h;
640 mg	Enzymatic reaction;
	Stage #1: stevioside With sodium periodate at 20℃; Stage #2: With potassium hydroxide Reflux;
	With sodium periodate; potassium hydroxide In water
	Stage #1: stevioside With sodium periodate In water at 20℃; for 18h; Inert atmosphere; Stage #2: With potassium hydroxide In water for 2h; Inert atmosphere; Reflux;
	With β-glucosidase from Penicillium multicolour In aq. phosphate buffer; water at 60℃; for 12h;	Preparation of steviol from steviosidewith β-glucosidase For a typical reaction, Stv aqueous medium (5 g/L) andβ-glucosidase 2.37 kU/g Stv were mixed in 50 mM sodiumphosphate buffer (pH 5.6), and then the mixture was heated at 60 °C for 12 h. The hydrolysis product was precipitated from the reaction solution. The final product was obtained after recrystallization twice from 95% methanol aqueous solution. The product was characterized with NMR (contrastwith previous reports [14, 29]) and LC-MS (m/z: 317.4,[Msteviol-H]-).
	Stage #1: stevioside With sodium periodate In water at 20℃; Stage #2: With potassium hydroxide at 5 - 102℃;	[0057] Steviol was obtained by the following approach. Sodium periodate was added to a container containing stevioside (Cat. No. S0594, Tokyo Chemical Industry or Cat. No. S623, AK Scientific) and purified water, and the mixture was stirred overnight at room temperature. Potassium hydroxide was added thereto at internal temperature of 5 to 10°C under ice cooling, and the mixture was heated at internal temperature of 100 to 102°C for 2 hours. After confirmation of the completion of the reaction by HPLC, acetic acid was added thereto at internal temperature of 10 to 13°C under ice cooling. Next, extraction with ethyl acetate was performed three times, and the obtained organic layer was washed with a 10% aqueous sodium sulfite solution and subsequently with saline. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure at 40°C to obtain a crude product of a yellow solid. Methanol was added thereto, and the mixture was stirred for approximately 15 minutes. Then, purified water was added thereto, and a solid was collected by filtration. The solid collected by filtration was dried overnight at 50°C to obtain a white solid. This solid was dissolved in acetone at 50°C, followed by clarifying filtration. The filtrate was concentrated, and the obtained solid was dried under reduced pressure overnight at 50°C to obtain steviol of interest (purity: 98% (HPLC), acetone: 0.5 wt%). Steviol thus obtained was employed in the following experiments.
	Stage #1: stevioside With sodium periodate In water at 20℃; Stage #2: With potassium hydroxide at 5 - 102℃;	[0057] Steviol was obtained by the following approach. Sodium periodate was added to a container containing stevioside (Cat. No. S0594, Tokyo Chemical Industry or Cat. No. S623, AK Scientific) and purified water, and the mixture was stirred overnight at room temperature. Potassium hydroxide was added thereto at internal temperature of 5 to 10°C under ice cooling, and the mixture was heated at internal temperature of 100 to 102°C for 2 hours. After confirmation of the completion of the reaction by HPLC, acetic acid was added thereto at internal temperature of 10 to 13°C under ice cooling. Next, extraction with ethyl acetate was performed three times, and the obtained organic layer was washed with a 10% aqueous sodium sulfite solution and subsequently with saline. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure at 40°C to obtain a crude product of a yellow solid. Methanol was added thereto, and the mixture was stirred for approximately 15 minutes. Then, purified water was added thereto, and a solid was collected by filtration. The solid collected by filtration was dried overnight at 50°C to obtain a white solid. This solid was dissolved in acetone at 50°C, followed by clarifying filtration. The filtrate was concentrated, and the obtained solid was dried under reduced pressure overnight at 50°C to obtain steviol of interest (purity: 98% (HPLC), acetone: 0.5 wt%). Steviol thus obtained was employed in the following experiments.
57 %	Stage #1: stevioside With sodium periodate In water at 25℃; Stage #2: With potassium hydroxide In water at 100℃;
	Stage #1: stevioside With sodium periodate In water at 20℃; Stage #2: With potassium hydroxide at 5 - 102℃;	[0057] Steviol was obtained by the following approach. Sodium periodate was added to a container containing stevioside (Cat. No. S0594, Tokyo Chemical Industry or Cat. No. S623, AK Scientific) and purified water, and the mixture was stirred overnight at room temperature. Potassium hydroxide was added thereto at internal temperature of 5 to 10°C under ice cooling, and the mixture was heated at internal temperature of 100 to 102°C for 2 hours. After confirmation of the completion of the reaction by HPLC, acetic acid was added thereto at internal temperature of 10 to 13°C under ice cooling. Next, extraction with ethyl acetate was performed three times, and the obtained organic layer was washed with a 10% aqueous sodium sulfite solution and subsequently with saline. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure at 40°C to obtain a crude product of a yellow solid. Methanol was added thereto, and the mixture was stirred for approximately 15 minutes. Then, purified water was added thereto, and a solid was collected by filtration. The solid collected by filtration was dried overnight at 50°C to obtain a white solid. This solid was dissolved in acetone at 50°C, followed by clarifying filtration. The filtrate was concentrated, and the obtained solid was dried under reduced pressure overnight at 50°C to obtain steviol of interest (purity: 98% (HPLC), acetone: 0.5 wt%). Steviol thus obtained was employed in the following experiments.

Reference： [1]Lin, Zhaomin; Guo, Yanxia; Gao, Yanhui; Wang, Shuqi; Wang, Xiaoning; Xie, Zhiyu; Niu, Huanmin; Chang, Wenqiang; Liu, Lei; Yuan, Huiqing; Lou, Hongxiang [Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3944 - 3956]
[2]Location in patent: scheme or table Shi, Lian-Yong; Wu, Jia-Qiang; Zhang, Da-Yong; Wu, Yang-Chang; Hua, Wei-Yi; Wu, Xiao-Ming [Synthesis, 2011, # 23, p. 3807 - 3814]
[3]Nagy, Viktória; Ozsvár, Dániel; Szakonyi, Zsolt; Zupkó, István [International Journal of Molecular Sciences, 2020, vol. 21, # 1]
[4]Ukiya, Motohiko; Sawada, Shingo; Kikuchi, Takashi; Kushi, Yasunori; Fukatsu, Makoto; Akihisa, Toshihiro [Chemistry and biodiversity, 2013, vol. 10, # 2, p. 177 - 188]
[5]Isaza, Laura; Murillo, Jilmar. A.; Olivo, Horacio F.; Pineda, Tatiana; Quinones, Winston; Robledo, Sara M.; Torres, Fernando; echeverri, Fernando; escobar, Gustavo A. [European Journal of Organic Chemistry, 2021, vol. 2021, # 23, p. 3386 - 3397]
[6]Ogawa, Tomoya; Nozaki, Michio; Matsui, Masanao [Tetrahedron, 1980, vol. 36, p. 2641 - 2648]
[7]Current Patent Assignee: TAN - EP1757282, 2007, A1 Location in patent: Page/Page column 10
[8]Location in patent: experimental part Takasaki, Midori; Konoshima, Takao; Kozuka, Mutsuo; Tokuda, Harukuni; Takayasu, Junko; Nishino, Hoyoku; Miyakoshi, Masazumi; Mizutani, Kenji; Lee, Kuo-Hsiung [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 2, p. 600 - 605]
[9]Ibrahim, Mohamed A.; Rodenburg, Douglas L.; Alves, Kamilla; Fronczek, Frank R.; McChesney, James D.; Wu, Chongming; Nettles, Brian J.; Venkataraman, Sylesh K.; Jaksch, Frank [Journal of Natural Products, 2014, vol. 77, # 5, p. 1231 - 1235]
[10]Lin, Shwu-Jiuan; Su, Ta-Chi; Chu, Chin-Nan; Chang, Yi-Chih; Yang, Li-Ming; Kuo, Yu-Cheng; Huang, Tsurng-Juhn [Journal of Natural Products, 2016, vol. 79, # 12, p. 3057 - 3064]
[11]Current Patent Assignee: CHINA PHARMACEUTICAL UNIVERSITY - CN103819484, 2017, B Location in patent: Page/Page column 15
[12]Kobayashi, Shoji; Shibukawa, Keisuke; Hamada, Yoshiki; Kuruma, Takuma; Kawabata, Asako; Masuyama, Araki [Journal of Organic Chemistry, 2018, vol. 83, # 3, p. 1606 - 1613]
[13]Wan, Hui-da; Ni, Yao; Zhang, Hong-jian; Li, Dan; Wang, Da-wei [Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2019, vol. 93, # 3-4, p. 193 - 201]
[14]Current Patent Assignee: KOTOBUKI FUDOSAN (KABUSHIKI KAISHA) LTD - EP4082540, 2022, A1 Location in patent: Page/Page column 9; 10
[15]Current Patent Assignee: KOTOBUKI FUDOSAN (KABUSHIKI KAISHA) LTD - EP4082540, 2022, A1 Location in patent: Page/Page column 9; 10
[16]Bai, Dorottya; Schelz, Zsuzsanna; Erdős, Dóra; Kis, Anna K.; Nagy, Viktória; Zupkó, István; Balogh, György T.; Szakonyi, Zsolt [International Journal of Molecular Sciences, 2023, vol. 24, # 2]
[17]Current Patent Assignee: KOTOBUKI FUDOSAN (KABUSHIKI KAISHA) LTD - EP4082540, 2022, A1 Location in patent: Page/Page column 9; 10

2
[ 57817-89-7 ]
[ 27975-19-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sulfuric acid; In water;	Ent-16-oxobeyeran-19-oic acid was synthesized by hydrolysis of stevioside with 10% sulfuric acid [48] . Yield 93%; Mp 228.4-230.8 C; IR (KBr): 3448, 2955, 2924, 2848, 1736, 1692, 1453, 1404, 1373, 1320, 1268, 1214, 1180, 1150, 1108, 973, 950, 796, 589 cm-1; 1H NMR (400 MHz, CDCl3, ppm): delta 2.64 (dd, J = 18.64, 3.76 Hz, 1H), 2.17 (d, J = 13.40 Hz, 1H), 1.90-1.37 (m, 13H), 1.25 (s, 3H), 1.22-1.14 (m, 3H), 1.06-1.03 (m, 1H), 0.98 (s, 3H), 0.95-0.88 (m, 1H), 0.78 (s, 3H); 13C NMR (100 MHz, CDCl3, ppm): delta 224.22, 184.33, 56.79, 57.62, 56.09, 54.83, 49.73, 49.59, 44.38, 42.02, 40.42, 40.42, 38.99, 38.34, 32.80, 29.69, 22.32, 20.57, 19.55, 14.04; HRMS (ESI, m/z) calcd for C20H30O3Na [M + Na]+ 341.2093. Found: 341.2085.
	Acidic aqueous solution;	Chemical: Compound A, (ent-17-norkaurane-16-oxo-18-oic acid, molecular formula, C20H40O3, Molecular weight: 318.5) is produced from stevioside through acidic hydrolysis, crystallization and purification. The structure of compound A are confirmed by inferred analysis and NMR, which are consistence with previously published data. The purity of compound A is greater than 99% determined by high performance liquid chromatograph.
	With sulfuric acid; at 60 - 70℃; for 6h;	Preparation of ADIS The pulverized, dry S. rebaudina leaves were successively extracted with n-hexane, ethyl acetate, and methanol. The methanol extract was subjected to silica column chromatography to yield stevioside. ADIS was obtained from stevioside as described previously ( Wonganan et al., 2013 ). Briefly, stevioside was dissolved in 20% sulfuric acid solution and then heated at 60-70 C for 6 h with stirring. The mixture was extracted with ethyl acetate.

With sulfuric acid;Heating;

stevioside(4.0 g) in a round bottom flask.It was dissolved by adding 10% H 2 SO 4 and stirred under heating.After completion of the reaction, the system was cooled to room temperature, filtered, and washed with water to give Compound 2 as a white solid.

Reference： [1]Chemistry and biodiversity,2013,vol. 10,p. 177 - 188
[2]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 2485 - 2490
[3]European Journal of Medicinal Chemistry,2016,vol. 115,p. 26 - 40
[4]Journal of Chemical Crystallography,2009,vol. 39,p. 108 - 111
[5]Journal of Chemical Crystallography,2011,vol. 41,p. 519 - 522
[6]Journal of Natural Products,2002,vol. 65,p. 273 - 277
[7]Life Sciences,2005,vol. 77,p. 2127 - 2140
[8]Journal of the American Chemical Society,2007,vol. 129,p. 12453 - 12460
[9]Patent: EP1757282,2007,A1 .Location in patent: Page/Page column 10
[10]Planta Medica,2008,vol. 74,p. 816 - 821
[11]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 1464 - 1473
[12]European Journal of Medicinal Chemistry,2013,vol. 65,p. 70 - 82
[13]Life Sciences,2014,vol. 116,p. 31 - 36
[14]Food Chemistry,2016,vol. 190,p. 270 - 275
[15]Patent: CN108456240,2018,A .Location in patent: Paragraph 0063-0065
[16]Journal of Agricultural and Food Chemistry,2020,vol. 68,p. 4624 - 4631

3
[ 57817-89-7 ]
[ 41093-60-1 ]

Yield	Reaction Conditions	Operation in experiment
87.5%	With sodium hydroxide In methanol at 60℃; for 7h;	2.3 Hydrolysis of stevioside 1 (Hyd. ST) Stevioside (1, 5g, 6.21mmol) was added to 50 ml of 100 mmol NaOH (4 g dissolved in 50 ml MeOH at room temperature) and the mixture was heated at 60°C. The mixture was refluxed for 7 h under continuous stirring. The mixture was cooled to room temperature and then neutralised with 1N HCl. To obtain the product, two methods were employed as follows; Method A: the mixture was concentrated under vacuum to give a white solid, which was recrystallised from methanol-acetone (1:1) to yield pure 2 (2.99 g, 75.0%, mp 198-199°C). Method B: the product was extracted with n-BuOH. The n-BuOH layer was washed with water and concentrated under vacuum to afford a crude solid which was recrystallised from methanol-acetone (1:1) mixture to yield pure 2 (3.48 g, 87.5%, mp 198-199°C). The compound obtained had the following characteristics; IR (KBr): 3500-3300 (br., O-H), 2917.69 (SP3 C-H), 1720 (C=O acid), 1642.9 (C=C)cm-1. 1HNMR (CDCl3): δ0.83-0.86 (m, 1H, CH), 0.94 (s, 3H, CH3), 0.97-1.09 (m, 2H, CH), 1.16 (s, 3H, CH3), 1.39-1.43 (m, 2H, CH), 1.48-1.53 (m, 3H, CH), 1.57-1.69 (m, 1H, CH), 1.77-1.93 (m, 6H, CH), 2.01-2.14 (m, 3H, CH), 2.17-2.20 (m, 2H, CH), 3.29-3.62 (m, 16H, 13 CH-O, 3 OH, D2O exchangeable), 4.58-4.66 (m, 7H, O-CH-O, =CH2, 4 OH), 5.22-5.27 (m, 1H, O-CH-O). 13C NMR: δ15.23, 15.42, 18.93, 19.89, 20.00, 21.86, 21.93, 28.04, 28.11, 29.43, 37.31, 37.74, 37.89, 39.35, 40.64, 41.28, 41.41, 41.71, 43.37, 44.13, 44.25, 53.67, 53.80, 56.64, 56.73, 61.17, 61.36, 61.89, 62.37, 68.75, 70.07, 70.19, 70.60, 71.09, 74.04, 74.91, 76.44, 76.54, 76.84, 76.90, 76.94, 76.99, 77.16, 77.32, 78.59, 80.71, 86.48, 87.02, 87.74, 95.78, 96.03, 102.37, 102.94, 104.62, 152.32, 180.55. Analytically calculated for C32H50O13: C, 59.80; H, 7.84; found: C, 60.08; H, 8.11.
	With potassium hydroxide
	With water; sodium hydroxide at 100℃; for 1h;

	With water Alkaline conditions;
	With potassium hydroxide In water for 1h; Reflux;
	With potassium hydroxide In water
	With potassium hydroxide
	With methanol; sodium hydroxide at 70℃; Inert atmosphere;	7; 9 EXAMPLE 7: PREPARATION OF CC-00405 To a stirred solution of 19 (5.0 g, 6.21 mmol) in methanol (150 mL) NaOH (9.44 g, 236.06 mmol) was added in one lot at room temperature and stirred at reflux condition for 16 h. After completion of the reaction (TLC monitored), reaction mixture was cooled to room temperature, Acidified with 1 N HC1 (pH 4.0-5.0) at 10 °C, the solvent was evaporated under reduced pressure and compound was extracted with n-butanol (3 c 50 mL). The combined organic layer was washed with water and concentrated under reduced pressure. The crude compound was azeotrope with methanol: acetonitrile (1 : 1) (3 c 30 mL) to afford 20 (3.2 g) as a white solid. (Note: crude product was directly used in the next step). ESI MS: m/z 665 [M+Na]+; NMR (400 MHz, DMSO-de): d 5.68 (s, 1H), 5.41 (d, J= 3.2Hz, 1H), 5.12-4.88 (m, 4H), 4.74 (s, 1H), 4.48 (d, J= 7.6 Hz, 1H), 4.43-4.38 (m, 1H), 4.36 (d, J= 7.6Hz, 1H), 4.25-4.17 (m, 1H), 4.15-4.10 (m, 1H), 3.63-3.53 (m, 2H), 3.51-3.37 (m, 3H), 3.27-2.96 (m, 6H), 2.13-1.65 (m, 9H), 1.54-1.28 (m, 7H), 1.10 (s, 3H), 1.03-0.90 (m, 3H), 0.87 (s, 3H), 0.83-0.72 (m, 1H).
	With sodium hydroxide at 100℃; for 0.25h;
85 %	With sodium hydroxide In methanol at 60℃;	1 <Example 1>Hydrolysis of stevioside through alkali catalysis Add 402.5 mg (0.5 mmol) stevioside to 12.5 mL NaOH solution (1.0 g NaOH/12.5 mL methanol) and react at 60 ° C for 5 hours. The reaction solution was neutralized with 1N HCl at room temperature and extracted three times with n-butanol.The organic layer was collected, washed with water, and distilled under reduced pressure to obtain a crude solid product. This crude solid product was recrystallized from methanol-acetone 1:1 mixture to obtain steviolbioside (273mg, 85% (mol/mol) yield) as a purified steviol monoglycoside-acid.

Reference： [1]Khattab, Sherine N.; Massoud, Mona I.; Jad, Yahya El-Sayed; Bekhit, Adnan A.; El-Faham, Ayman [Food Chemistry, 2015, vol. 173, p. 979 - 985]
[2]Location in patent: scheme or table Sharipova; Strobykina, I. Yu.; Kataev; Lodochnikova; Gubaidullin [Russian Journal of General Chemistry, 2009, vol. 79, # 12, p. 2695 - 2697]
[3]Location in patent: scheme or table Kataev; Strobykina; Andreeva; Garifullin; Sharipova; Mironov; Chestnova [Russian Journal of Bioorganic Chemistry, 2011, vol. 37, # 4, p. 483 - 491]
[4]Location in patent: experimental part Hellfritsch, Caroline; Brockhoff, Anne; Staehler, Frauke; Meyerhof, Wolfgang; Hofmann, Thomas [Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 27, p. 6782 - 6793]
[5]Bartholomees, Uria; Struyf, Tom; Lauwers, Olivier; Ceunen, Stijn; Geuns, Jan M.C. [Food Chemistry, 2016, vol. 190, p. 270 - 275]
[6]Sharipova; Garifullin; Andreeva; Strobykina; Bazanova; Kataev [Russian Journal of General Chemistry, 2015, vol. 85, # 6, p. 1456 - 1466][Zh. Obshch. Khim., 2015, vol. 85, # 6, p. 989 - 999,11] Sharipova; Andreeva; Strobykina, I. Yu.; Voloshina; Strobykina; Kataev [Chemistry of Natural Compounds, 2017, vol. 53, # 6, p. 1107 - 1111][Khim. Prir. Soedin., 2017, # 6, p. 941 - 944,4]
[7]Sharipova; Garifullin; Andreeva; Strobykina, I. Yu.; Kataev [Russian Journal of General Chemistry, 2016, vol. 86, # 8, p. 1871 - 1880][Zh. Obshch. Khim., 2016, vol. 86, # 8, p. 1334 - 1344,11] Sharipova; Garifullin; Andreeva; Strobykina, I. Yu.; Kataev [Chemistry of Natural Compounds, 2016, vol. 52, # 5, p. 870 - 873][Khim. Prir. Soedin., 2016, # 5, p. 742 - 745]
[8]Current Patent Assignee: COCA-COLA CO - WO2019/147617, 2019, A1 Location in patent: Page/Page column 99; 111-112; 121-122
[9]Cao, Xueting; Jiang, Xukai; Xiao, Min; Xu, Li; Yan, Zhenxin; Yang, Shida; Yang, Xiao [Frontiers in Microbiology, 2021, vol. 12]
[10]Current Patent Assignee: PYO, Sang Hyun - WO2022/220521, 2022, A1 Location in patent: Paragraph 127-128

Yield	Reaction Conditions	Operation in experiment
	With NH(CH2)2NH2 functionalized polymethacrylate/DVB co-polymer absorbent resin; In methanol; acetone; at 20℃;Purification / work up;	Purification of Preparation 2The crude material (produced by Experiment 2) was loaded onto the top of an 8 liter low pressure preparative chromatography column packed with NH(CH2)2NH2 functionalized polymethacrylate/DVB co-polymer absorbent resin, eluted with 10% methanol in acetone for 2 bed volumes, then eluted with 14% methanol in acetone to yield fractions that contain stevioside. After stevioside was washed out, the column was eluted with 20% methanol in acetone to yield fractions containing <strong>[58543-16-1]rebaudioside A</strong> and stevioside.The fractions containing stevioside were collected and combined, then concentrated to dryness. The residue was then dissolved in hot methanol and then kept at room temperature overnight. The resultant needle-like crystals were filtered out and dried in a vacuum oven to yield 375 g of stevioside as a white crystalline powder whose purity was >99%.The fractions containing <strong>[58543-16-1]rebaudioside A</strong> were collected and concentrated to dryness in a rotary evaporator at 50 C. under vacuum. The residue was then dissolved in a small amount of hot methanol, and acetone was added to the methanol solution (the ratio of methanol to acetone is 15:85). The mixture was kept at room temperature overnight, and the needle like crystals that formed were collected through filtration. The crystals were then dried in a vacuum oven to yield 55 grams of <strong>[58543-16-1]rebaudioside A</strong> whose purity was 98.4%.
	With NH(CH2)2NH2 functionalized polymethacrylate/DVB co-polymer absorbent resin; In methanol; acetone; at 20 - 50℃;Purification / work up;	Purification of Preparation 2The crude material (produced by Experiment 2) was loaded onto the top of an 8 liter low pressure preparative chromatography column packed with NH(CH2)2NH2 functionalized polymethacrylate/DVB co-polymer absorbent resin, eluted with 10% methanol in acetone for 2 bed volumes, then eluted with 14% methanol in acetone to yield fractions that contain stevioside. After stevioside was washed out, the column was eluted with 20% methanol in acetone to yield fractions containing <strong>[58543-16-1]rebaudioside A</strong> and stevioside.The fractions containing stevioside were collected and combined, then concentrated to dryness. The residue was then dissolved in hot methanol and then kept at room temperature overnight. The resultant needle-like crystals were filtered out and dried in a vacuum oven to yield 375 g of stevioside as a white crystalline powder whose purity was >99%.The fractions containing <strong>[58543-16-1]rebaudioside A</strong> were collected and concentrated to dryness in a rotary evaporator at 50 C. under vacuum. The residue was then dissolved in a small amount of hot methanol, and acetone was added to the methanol solution (the ratio of methanol to acetone is 15:85). The mixture was kept at room temperature overnight, and the needle like crystals that formed were collected through filtration. The crystals were then dried in a vacuum oven to yield 55 grams of <strong>[58543-16-1]rebaudioside A</strong> whose purity was 98.4%.

5
[ 133-89-1 ]
[ 57817-89-7 ]
[ 58543-16-1 ]

Yield	Reaction Conditions	Operation in experiment
	With UDP-glucosyltransferase UGT76G1; magnesium chloride; In aq. phosphate buffer; at 30℃;pH 7.2;Enzymatic reaction;Catalytic behavior; Kinetics;	The total volume of the reaction was 5.0 mL with the following composition: 50 mM sodium phosphate buffer pH 7.2, 3 mM MgCl2, 2.5 mM UDP-glucose, 0.5 mM Stevioside and 500 mu^ of UGT76G1 thawed lysate. The reactions were run at 30 C on an orbitary shaker at 135 rpm. For each sample, 460 muEpsilon of the reaction mixture was quenched with 40 mu, of 2N H2S04 and 420 mu, of methanol/water (6/4). The samples were immediately centrifuged and kept at 10 C before analysis by HPLC (CAD). HPLC indicated almost complete conversion of stevioside to rebaudioside A as seen in Figure 40
	With UGT76G1; magnesium chloride; In aq. phosphate buffer; at 30℃;	EXAMPLE 4Catalytic reaction with in-vivo produced UGT76G1The total volume of the reaction was 5.0 mL with the following composition: 50 mM sodium phosphate buffer pH 7.2, 3 mM MgCl2, 2.5 mM UDP-glucose, 0.5 mM Stevioside and 500 muL of UGT76G1 thawed lysate. The reactions were run at 30 C on an orbitary shaker at 135 rpm. For each sample, 460 muL of the reaction mixture was quenched with 40 muL of 2N H2SO4and 420 muL of methanol/water (6/4). The samples were immediately centrifuged and kept at 10 C before analysis by HPLC (CAD). HPLC indicated almost complete conversion of stevioside to rebaudioside A, as shown in FIG. 51.

Reference： [1]Patent: WO2014/193888,2014,A1 .Location in patent: Page/Page column 9; 46-47; 52-53
[2]Patent: WO2016/43926,2016,A1 .Location in patent: Page/Page column 47

6
[ 952585-00-1 ]
[ 57817-89-7 ]
[ 58543-16-1 ]

Yield	Reaction Conditions	Operation in experiment
	With UDP-glucosyltransferase from Stevia rebaudiana, recombinant; magnesium chloride; In aq. phosphate buffer; at 30℃; for 1h;pH 7.2;Enzymatic reaction;	The UGT76G1 expressed by E. coli was subjected to the enzyme assay reaction. The assay mixture contained 1 mg of total protein from the crude extract, 1 mM stevioside, 2 mM UDP-glucose, and 3 mM MgCl2 in potassium phosphate buffer (100 mM, pH 7.2), in a total volume of 5 mL. Reactions were performed at 30 C for 1 h. The samples were taken and prepared for high-performance liquid chromatography (HPLC) analysis. One unit (U) of glucosyltransferase activity was defined as the amount of enzyme that produced 1 mumol of rebaudioside A per min under the described conditions.

Reference： [1]Bioscience, Biotechnology and Biochemistry,2016,vol. 80,p. 67 - 73

7
[ 57817-89-7 ]
[ 57-50-1 ]
[ 58543-16-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With Arabidopsis thaliana sucrose synthase gene; UDP-glucosyltransferase from Stevia rebaudiana, recombinant; magnesium chloride; In aq. phosphate buffer; at 30℃; for 30h;pH 7.2;Enzymatic reaction;	After pEUGT-SUS expressionin E. coli, the cells were harvested and washed twice in potassium phosphate buffer (100 mM, pH 7.2). A lysate containing soluble proteins was obtained by sonication on an ice-water bath and subsequent clarification by centrifugation at 4 C. The supernatant was used as the crude extract. Total protein concentrations were measured by the Bradford assay using bovine serum albumin (BSA) as a standard.23) The substratestevioside was incubated with aliquots of the crude extract at 30 C in a reaction mixture containing varying concentrations of UDP-glucose or UDP, sucrose, and 3 mM MgCl2 in potassium phosphate buffer (100 mM, pH 7.2) for synthesis of rebaudioside A.

Reference： [1]Bioscience, Biotechnology and Biochemistry,2016,vol. 80,p. 67 - 73

8
[ 57817-89-7 ]
[ 58543-16-1 ]

Yield	Reaction Conditions	Operation in experiment
150 mg	With beta-1,3-glucanase from Irpex lacteus; In aq. buffer; at 55℃; for 3h;pH 4.5;Enzymatic reaction;	Stevioside (200 mg) and curdlan (400 mg) was dissolved in citrate buffer (0.1 M with pH 4.5) and beta-1,3-glucanase 3.425 U/g was added. The reaction mixture was shaking in an incubator for 3 hr at 55 C. The reaction mixture was cooled to room temperature and the enzyme was deactivated by boiling at 100 C. Progress of the reaction was monitored by TLC using solvent system ethyl acetate/ethanol/H2O (8:2:1.2, v/v/v) (Jaitak et al., 2009a,b). The developed plate was dried and spots were visualized by spraying with 5% sulfuric acid. Reaction mixture was passed through the Dianion HP-20, followed by washing with methanol. Methanol fraction was dried over rota vapor and recrystallized using cold ethanol to yield 150 mg of pure Rebaudioside A. Product was confirmed by, NMR, HRMS and melting point determination. Rebaudioside A: MP 245-247 C, Rf value 0.45, ethyl acetate:ethanol:water (8:2:1.2, v/v/v), 1H NMR (400 MHz, DMSO): 5.64 (1H, d, J = 8 Hz), 5.28 (1H, d, J = 8 Hz), 5.02 (1H, t, J = 8 Hz) and 4.95 (1H, d, J = 8 Hz). 13C-NMR (100 MHz, DMSO): deltac 14.89, 18.56, 19.79, 21.14, 28.04, 37.48, 38.70, 39.20, 40.03, 41.04, 41.64, 43.10, 43.20, 47.0, 53.23, 56.52, 60.56, 61.02, 61.34, 68.90, 69.48, 70.01, 70.32, 72.44, 73.59, 74.35, 75.98, 76.49, 76.88, 76.98, 77.42, 78.46, 78.79, 78.88, 79.12, 85.40, 86.27, 94.45, 96.45, 102.47, 102.98, 104.0, 152.78, 175.63. HRMS (ESI): m/z calc.for C44H70O23 [M-H]: 965.4230; found 965.5040.

Reference： [1]Phytochemistry,2016,vol. 125,p. 106 - 111

9
[ 57817-89-7 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
65.1%	With sulfuric acid at 75℃; for 5h;	1 Preparation of compound (V) 10 g of stevioside (IV) was placed in a 1000 mL round bottom flask and 10 wt%Of dilute sulfuric acid solution 600mL, magnetic stirring, oil bath 75 ° C. After lh reaction, a small amount of yellow flocculent solid was produced and the reaction was continued for 4 h to stop the reaction from cooling to room temperature. The resulting yellow solid was transferred to a 100 mL single-necked flask and recrystallized from acetone. The crystals were allowed to cool and the white crystals were slowly precipitated, i.e., compound (V). Yield: 65.1%
65.1%	With sulfuric acid In water at 75℃; for 5h;	1 Example 1: Preparation of Compound (III) 10 g of stevioside (II) was placed in a 1000 mL round bottom flask, and 600 mL of a 10 wt% dilute sulfuric acid solution was slowly added, and magnetically stirred, and the oil bath was 75 °C. After 1 h of reaction, a small amount of yellow flocculent solid was produced, and the reaction was continued for 4 h, and the reaction was stopped and cooled to room temperature. After suction filtration, the yellow solid obtained by suction filtration was transferred to a 100 mL single-necked flask and recrystallized from acetone, and placed under cooling, and white crystals were slowly precipitated, and dried by filtration to obtain 2.98 g of Compound (III).

Reference： [1]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN105399644, 2016, A Location in patent: Paragraph 0032; 0033
[2]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN109053484, 2018, A Location in patent: Paragraph 0031; 0032

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[ 57817-89-7 ] Synthesis Path-Upstream 1~12

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