Name: 7464-56-4|Allyl a-D-glucopyranoside|97%
Brand: Ambeed
SKU: A515383
Rating: 96 (22 reviews)

1
[ 50-99-7 ]
[ 107-18-6 ]
[ 7464-56-4 ]

Yield	Reaction Conditions	Operation in experiment
40%	With Dowex 15 (H⁺) for 2h; Reflux;
	With hydrogenchloride
	With hydrogenchloride Heating;

With methanesulfonic acid at 105℃; for 10h;

Reference： [1]Location in patent: scheme or table Hassan, Hammed H.A.M. [Letters in Organic Chemistry, 2010, vol. 7, # 2, p. 127 - 135]
[2]Talley et al. [Journal of the American Chemical Society, 1945, vol. 67, p. 2037] Danielli et al. [Biochemical Journal, 1947, vol. 41, p. 325,332]
[3]Hetfleisch-Stephan; Schunk; Rudiger [Pharmazie, 1994, vol. 49, # 2-3, p. 125 - 130]
[4]Koto, Shinkiti; Shinoda, Yoshika; Hirooka, Motoko; Sekino, Akiko; Ishizumi, Sachiko; Koma, Mutsuko; Matuura, Chieko; Sakata, Naoko [Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 8, p. 1603 - 1615]

2
[ 106-95-6 ]
[ 7464-56-4 ]
[ 185564-68-5 ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: 1-O-allyl-α-D-glucopyranoside With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; Stage #2: allyl bromide In N,N-dimethyl-formamide at 0 - 20℃;
	With sodium hydroxide

Reference： [1]Location in patent: experimental part Hassan, Hammed H.A.M. [Letters in Organic Chemistry, 2010, vol. 7, # 2, p. 127 - 135]
[2]Talley et al. [Journal of the American Chemical Society, 1945, vol. 67, p. 2037]

3
[ 2280-44-6 ]
[ 107-18-6 ]
[ 7464-56-4 ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: allyl alcohol With acetyl chloride at 0℃; for 0.5h; Inert atmosphere; Stage #2: D-Glucose at 0 - 70℃; Inert atmosphere;
53%	Stage #1: allyl alcohol With acetyl chloride at 0℃; for 1h; Stage #2: D-Glucose at 70℃; for 5h;	Allyl α-D-glucopyranoside¹(5) Allyl alcohol (25 mL, 0.37 mol) was cooled to 0 °C, 6 (2.0 mL, 2.8 mmol) was added dropwise, and the mixture was stirred at 0 °C for 1 h. After heating to 70 °C, D-(+)-glucose (2.0 g, 11.1 mmol) was added and the reaction mixture was stirred under reflux for 5 h. It was neutralized with sodium hydrogen carbonate and filtered over Celite. After three co-distillations with toluene, the crude product was purified by flash column chromatography on silica (ethyl acetate/methanol, 8:2) to yield a colourless solid, 1.3 g, 5.9 mmol. Rf = 0.5 (ethyl acetate/ methanol, 8:2), yield: 53 %.
16%	With boron trifluoride diethyl etherate for 4h; Reflux;

	With 4 A molecular sieve; Dowex 50-X₈(H⁺) resin for 1.66667h; Heating;
	With Dowex (H⁺)
	With cation exchange resin QU-2 (H⁺) at 70℃; for 72h;
	With hydrogenchloride
	With acetyl chloride at 0 - 40℃;	1 Allyl alcohol (500 mL, 7.35 mol) was cooled to 0°C and acetyl chloride (72 mL, 1 .0 mol) was added slowly, keeping the reaction mixture below 5°C. D- Glucose monohydrate (200 g, 1 .0 mol) was added and the reaction mixture was stirred overnight at room temperature, then overnight at 40°C. The solvent was evaporated to provide a thick syrup, which was co-evaporated with toluene (500 mL) and used without further purification.
	for 2h; Inert atmosphere; Reflux;
	With boron trifluoride diethyl etherate at 115℃; for 8h;
	With trifluorormethanesulfonic acid at 0 - 80℃; for 48h;

Reference： [1]Schindler, Corinna S.; Bertschi, Louis; Carreira, Erick M. [Angewandte Chemie - International Edition, 2010, vol. 49, # 48, p. 9229 - 9232]
[2]Wang, Yanhui; Zhao, Xiaoke; Kong, Qiuyun; Yao, Jiajian; Meng, Xiangbao; Li, Zhongjun [Tetrahedron Letters, 2017, vol. 58, # 16, p. 1655 - 1658]
[3]Location in patent: experimental part Tursky, Matyas; Vesely, Jan; Tislerova, Iva; Trnka, Tomas; Ledvina, Miroslav [Synthesis, 2008, # 16, p. 2610 - 2616]
[4]Pelyvas, Istvan; Lindhorst, Thisbe; Thiem, Joachim [Liebigs Annalen der Chemie, 1990, # 8, p. 761 - 769]
[5]Holme, Kevin R.; Hall, Laurance D. [Carbohydrate Research, 1992, vol. 225, # 2, p. 291 - 306]
[6]Nepogod'ev, Sergey A.; Backinowsky, Leon V.; Grzeszczyk, Barbara; Zamojski, Aleksander [Carbohydrate Research, 1994, vol. 254, p. 43 - 60]
[7]Wolfenden, Mark L.; Cloninger, Mary J. [Journal of the American Chemical Society, 2005, vol. 127, # 35, p. 12168 - 12169]
[8]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - WO2011/137181, 2011, A1 Location in patent: Page/Page column 36
[9]Koch, Stefan; Schollmeyer, Dieter; Löwe, Holger; Kunz, Horst [Chemistry - A European Journal, 2013, vol. 19, # 22, p. 7020 - 7041]
[10]Tsai, Charng-Sheng; Chen, Chao-Tsen [Collection of Czechoslovak Chemical Communications, 2012, vol. 77, # 4, p. 314 - 322]
[11]Ruike, Tatsushi; Kanai, Yoshihiro; Iwabata, Kazuki; Matsumoto, Yuki; Murata, Hiroshi; Ishima, Masahiro; Ohta, Keisuke; Oshige, Masahiko; Katsura, Shinji; Kuramochi, Koji; Kamisuki, Shinji; Sahara, Hiroeki; Miura, Masahiko; Sugawara, Fumio; Sakaguchi, Kengo [Xenobiotica, 2018, p. 1 - 17]

4
[ 2280-44-6 ]
[ 107-18-6 ]
allyl β-D-glucopyranoside [ No CAS ]
[ 7464-56-4 ]

Yield	Reaction Conditions	Operation in experiment
14%	With Dowex 50-X₂-100 (H⁺) for 1.5h; Heating;
	With trifluorormethanesulfonic acid In dimethyl sulfoxide at 90℃; for 48h; Yield given. Yields of byproduct given;
	With Dowex-50 X-2 for 1.5h; Heating;

	With hydrogenchloride at 70℃; for 6h; Title compound not separated from byproducts;
	With Dowex-50 X-2 for 1.5h; Heating; Title compound not separated from byproducts;
	With trifluoroacetic acid at 105℃; for 26h;
	With Amberlite IR-120(H⁺) at 50℃; for 17h; Inert atmosphere; Ionic liquid; optical yield given as %de; stereoselective reaction;
	With scandium tris(trifluoromethanesulfonate) at 80℃; for 24h; Ionic liquid; optical yield given as %de; diastereoselective reaction;
	With carbon-based solid acid catalyst at 80℃; for 8h; Neat (no solvent); optical yield given as %de; diastereoselective reaction;
34 % de	With hydrogenchloride In water for 2h; Reflux; Inert atmosphere; Overall yield = 62.4 %; Overall yield = 7.62 g;

Reference： [1]Jenkins, David J.; Potter, Barry V.L. [Carbohydrate Research, 1996, vol. 287, # 2, p. 169 - 182]
[2]Konradsson, Peter; Roberts, Carmichael; Fraser-Reid, Bert [Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 1, p. 23 - 24]
[3]Jenkins; Potter [Journal of the Chemical Society. Chemical communications, 1995, # 11, p. 1169 - 1170]
[4]Nepogod'ev, Sergey A.; Backinowsky, Leon V.; Grzeszczyk, Barbara; Zamojski, Aleksander [Carbohydrate Research, 1994, vol. 254, p. 43 - 60]
[5]Jenkins; Potter [Journal of the Chemical Society. Chemical communications, 1995, # 11, p. 1169 - 1170]
[6]Fang, Tammy T.; Bendiak, Brad [Journal of the American Chemical Society, 2007, vol. 129, # 31, p. 9721 - 9736]
[7]Location in patent: experimental part Javier Munoz; Andre, Sabine; Gabius, Hans-Joachin; Sinisterra, Jose V.; Hernaiz, Maria J.; Linhardt, Robert J. [Green Chemistry, 2009, vol. 11, # 3, p. 373 - 379]
[8]Location in patent: scheme or table Auge, Jacques; Sizun, Gwenaelle [Green Chemistry, 2009, vol. 11, # 8, p. 1179 - 1183]
[9]Gorityala, Bala Kishan; Ma, Jimei; Pasunooti, Kalyan Kumar; Cai, Shuting; Liu, Xue-Wei [Green Chemistry, 2011, vol. 13, # 3, p. 573 - 577]
[10]Silverberg, Lee J.; Dillon, John L.; Vemishetti, Purushotham; Sleezer, Paul D.; Discordia, Robert P.; Hartung, Kerry B.; Gao, Qi [Organic Process Research and Development, 2000, vol. 4, # 1, p. 34 - 42]

5
[ 69304-37-6 ]
[ 7464-56-4 ]
[ 78120-20-4 ]

Yield	Reaction Conditions	Operation in experiment
69%	With 1H-imidazole In N,N-dimethyl-formamide for 1h; Ambient temperature;
36%	In pyridine at 0℃; for 1h;

Reference： [1]Ziegler; Eckhardt; Neumann; Birault [Synthesis, 1992, # 10, p. 1013 - 1017]
[2]Oltvoort, J. J.; Boeckel, C. A. A. van; Koning, J. H. de; Boom, J. H. van [Synthesis, 1981, # 4, p. 305 - 308]

6
[ 1125-88-8 ]
[ 7464-56-4 ]
[ 65987-12-4 ]

Yield	Reaction Conditions	Operation in experiment
57.2%	With toluenesulfonic acid monohydrate In N,N-dimethyl-formamide; acetonitrile at 0 - 40℃; for 16h;	1 In route B, allyl-4,6-O-benzylidene-α-D-glucopyranoside (structural formula) (2)) was synthesized. To the residue of Route A, add 100 mL each of anhydrous N, N-dimethylformamide and acetonitrile, cool to 0 ° C. under ice water, and benzaldehyde dimethylacetal (103 mL). And toluenesulfonic acid monohydrate (2.5 g) were added. Then, after heating and stirring at 40 ° C. for 16 hours, triethylamine (10 mL) was added to stop the reaction and concentrate under reduced pressure. The residue was poured into hexane (180 mL) and water (150 mL) and the mixture was vigorously stirred. The resulting precipitate was filtered off and washed with cold water and hexane in that order. The precipitate is further washed with hexane, cold water, and hexane in this order and filtered, and the precipitate is crystallized from ethanol to form a colorless acicular crystal, which is a compound represented by the structural formula (3). (28.6 g, 57.2%) was obtained.
	With toluene-4-sulfonic acid for 15h; Yield given;
	Yield given;

0.85 g	With methanesulfonic acid In N,N-dimethyl-formamide at 20℃;
34.5 g	With toluene-4-sulfonic acid In acetonitrile at 40℃; for 4h;

Reference： [1]Current Patent Assignee: GUNMA UNIVERSITY; M T 3 - JP6903273, 2021, B1 Location in patent: Paragraph 0021; 0044; 0046-0048
[2]Pelyvas, Istvan; Lindhorst, Thisbe; Thiem, Joachim [Liebigs Annalen der Chemie, 1990, # 8, p. 761 - 769]
[3]Yamada, Haruo; Harada, Takeo; Takahashi, Takashi [Journal of the American Chemical Society, 1994, vol. 116, # 17, p. 7919 - 7920]
[4]Koto, Shinkiti; Shinoda, Yoshika; Hirooka, Motoko; Sekino, Akiko; Ishizumi, Sachiko; Koma, Mutsuko; Matuura, Chieko; Sakata, Naoko [Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 8, p. 1603 - 1615]
[5]Ruike, Tatsushi; Kanai, Yoshihiro; Iwabata, Kazuki; Matsumoto, Yuki; Murata, Hiroshi; Ishima, Masahiro; Ohta, Keisuke; Oshige, Masahiko; Katsura, Shinji; Kuramochi, Koji; Kamisuki, Shinji; Sahara, Hiroeki; Miura, Masahiko; Sugawara, Fumio; Sakaguchi, Kengo [Xenobiotica, 2018, p. 1 - 17]

7
[ 76-83-5 ]
[ 7464-56-4 ]
[ 107242-80-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	In pyridine 23 degC, 12 h, 60 degC, 1 h;
	With pyridine for 17h; Ambient temperature;
	With pyridine; dmap at 80℃; for 16h;

Reference： [1]Hoos; Huixin; Vasella; Weiss [Helvetica Chimica Acta, 1996, vol. 79, # 7, p. 1757 - 1784]
[2]Nepogod'ev, Sergey A.; Backinowsky, Leon V.; Grzeszczyk, Barbara; Zamojski, Aleksander [Carbohydrate Research, 1994, vol. 254, p. 43 - 60]
[3]Zhang, Meimei; Du, Yuguo; Kong, Fanzuo [Carbohydrate Research, 2001, vol. 330, # 3, p. 319 - 324]

8
[ 100-52-7 ]
[ 7464-56-4 ]
[ 65987-12-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With zinc(II) chloride
70%	In N,N-dimethyl-formamide for 18h; Ambient temperature;
69%	With dimethyl sulfate In N,N-dimethyl-formamide for 18h; Ambient temperature;

39%

With trifluorormethanesulfonic acid; orthoformic acid triethyl ester In N,N-dimethyl-formamide at 20℃; for 72h;

Reference： [1]Ogawa, Tomoya; Kaburagi, Toshiaki [Carbohydrate Research, 1982, vol. 110, p. C12 - C15]
[2]Mani, Neelakandha S.; Kanakamma, Puthuparambil P. [Tetrahedron Letters, 1994, vol. 35, # 21, p. 3629 - 3632]
[3]Kanakamma, Puthuparampil P.; Mani, Neelakandha, S.; Maitra, Uday; Nair, Vijay [Journal of the Chemical Society. Perkin transactions I, 1995, # 18, p. 2339 - 2344]
[4]Location in patent: experimental part Tursky, Matyas; Vesely, Jan; Tislerova, Iva; Trnka, Tomas; Ledvina, Miroslav [Synthesis, 2008, # 16, p. 2610 - 2616]

9
[ 100-44-7 ]
[ 7464-56-4 ]
[ 6207-45-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydride In N,N-dimethyl-formamide for 15h;

Reference： [1]Lehmann, Jochen; Ziser, Lothar [Carbohydrate Research, 1992, vol. 225, # 1, p. 83 - 98]

10
[ 100-44-7 ]
[ 7464-56-4 ]
[ 83921-82-8 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium hydride at 100℃; for 3h;

Reference： [1]Koto, Shinkiti; Morishima, Naohiko; Shichi, Sonoko; Haigoh, Hisamitsu; Hirooka, Motoko; et al. [Bulletin of the Chemical Society of Japan, 1992, vol. 65, # 12, p. 3257 - 3274]

11
[ 7464-56-4 ]
2-O-α-D-glucopyranosyl-glycolaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With ozone In water-d2 for 0.133333h;
	With dimethylsulfide; ozone In methanol at -78℃; for 0.0833333h; Yield given;
	With dimethylsulfide; ozone 1) MeOH, -78 deg C, 2) r.t., 2 h; Multistep reaction;

	With dimethylsulfide; ozone 1.) MeOH, -78 deg C, 2.) MeOH, -10 deg C - r.t.; Yield given. Multistep reaction;
	With ozone
	Stage #1: 1-O-allyl-α-D-glucopyranoside With ozone In methanol at -78℃; Stage #2: With dimethylsulfide In methanol at -78 - 20℃; Inert atmosphere;	Oxime Neoglycoconjugates; General Procedure C General procedure: Ozone was bubbled through a solution of allyl glycoside 16 (250 mg)in MeOH (75 mL) at -78 °C until the solution turned blue (ca. 25 min). The solution was purged under N2 flow to remove the excess of ozone, and dimethyl sulfide (1 mL) was added. After a few minutes, nitrogen was again passed through the solution, which was then allowed to warm to r.t. The solvent was removed under reduced pressure to afford glycosyl aldehydes 29-39 (quant.) as a colorless oil. O-Benzylhydroxylamine hydrochloride (1.1 equiv) was then added to the solution of the corresponding glycosyl aldehydes (10 mg, 1 equiv) in H2O (1 mL). The mixture was stirred at 40 °C for 30 min and the final oxime was purified by semipreparative HPLC to obtain the Z/E mixture of neoglycoconjugates 47-58.

Reference： [1]Fang, Tammy T.; Zirrolli, Joseph; Bendiak, Brad [Carbohydrate Research, 2007, vol. 342, # 2, p. 217 - 235]
[2]Bernstein, Michael A.; Hall, Laurance D. [Carbohydrate Research, 1980, vol. 78, p. C1 - C3]
[3]Holme, Kevin R.; Hall, Laurance D. [Carbohydrate Research, 1992, vol. 225, # 2, p. 291 - 306]
[4]Hetfleisch-Stephan; Schunk; Rudiger [Pharmazie, 1994, vol. 49, # 2-3, p. 125 - 130]
[5]Weingarten, Saskia; Thiem, Joachim [Synlett, 2003, # 7, p. 1052 - 1054]
[6]Reina, José J.; Rioboo, Alicia; Montenegro, Javier [Synthesis, 2018, vol. 50, # 4, p. 831 - 845]

12
allyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside [ No CAS ]
[ 7464-56-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate for 3h; Ambient temperature;
	With water; triethylamine In methanol at 20℃; for 24h;
	Stage #1: allyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside With sodium methylate In methanol at 20℃; for 1h; Stage #2: In methanol	Deprotected Allyl Glycosides 8-14; General Procedure B General procedure: To a solution of protected glycosides (0.07 mmol) in anhydrous MeOH (1.5 mL), NaOMe (0.01 mmol) was added in one portion and the solution was stirred at r.t. After TLC showed a complete conversion (ca.1 h) Amberlite IRA 120H+ was added until pH 7 and the beads were filtered off. The solvent was evaporated under vacuum to obtain theα- and β-deprotected pyranosyl isomers of monosacharides 8-14.

Reference： [1]Nepogod'ev, Sergey A.; Backinowsky, Leon V.; Grzeszczyk, Barbara; Zamojski, Aleksander [Carbohydrate Research, 1994, vol. 254, p. 43 - 60]
[2]Konstantinović; Predojević; Gojković; Pavlović [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 3, p. 666 - 669]
[3]Reina, José J.; Rioboo, Alicia; Montenegro, Javier [Synthesis, 2018, vol. 50, # 4, p. 831 - 845]

13
[ 492-62-6 ]
[ 107-18-6 ]
[ 7464-56-4 ]

Yield	Reaction Conditions	Operation in experiment
	With Amberlite IR-120 (H⁺)
	With acetyl chloride Reflux;
	With camphor-10-sulfonic acid at 0 - 80℃; for 16h; Inert atmosphere;	1 In route A, allyl-α-D-glucopyranoside (structural formula (2)) was synthesized. The 500 mL eggplant flask was replaced with argon, and allyl alcohol (250 mL) was added. Α-D-Glucopyranose (structural formula (1)) (50 g) was added thereto with stirring. Camphor-sulfonic acid (1.9 g) was added while cooling to 0 ° C. under ice water. Then, it was taken out from the ice bath, returned to room temperature, heated to 80 ° C., and stirred for 16 hours. Then, the compound of structural formula (2) was obtained as a residue concentrated under reduced pressure.

With acetyl chloride Reflux;

Reference： [1]Yamada, Haruo; Harada, Takeo; Takahashi, Takashi [Journal of the American Chemical Society, 1994, vol. 116, # 17, p. 7919 - 7920]
[2]Pal, Rita; Das, Anupama; Jayaraman, Narayanaswamy [Chemical Communications, 2018, vol. 54, # 6, p. 588 - 590]
[3]Current Patent Assignee: GUNMA UNIVERSITY; M T 3 - JP6903273, 2021, B1 Location in patent: Paragraph 0021; 0044-0045
[4]Das, Anupama; Jayaraman, Narayanaswamy [Organic and Biomolecular Chemistry, 2021, vol. 19, # 42, p. 9318 - 9325]

14
[ 107-05-1 ]
[ 7464-56-4 ]
[ 185564-68-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium hydroxide; tetrabutylammomium bromide In water at 35℃; for 16h;
76%	With sodium hydroxide; tetrabutylammomium bromide In water at 35℃; for 16h;
76%	With tetrabutylammomium bromide; sodium hydride

72%	With sodium hydroxide; tetrabutylammomium bromide at 30℃; for 18h;
72%	With sodium hydroxide; tetrabutylammomium bromide

Reference： [1]Kieburg, Christoffer; Dubber, Michael; Lindhorst, Thisbe K. [Synlett, 1997, # 12, p. 1447 - 1449]
[2]Dubber, Michael; Lindhorst, Thisbe K. [Chemical Communications, 1998, # 12, p. 1265 - 1266]
[3]Lindhorst, Thisbe K.; Dubber, Michael [Carbohydrate Research, 2015, vol. 403, p. 90 - 97]
[4]Dubber, Michael; Lindhorst, Thisbe K. [Carbohydrate Research, 1998, vol. 310, # 1-2, p. 35 - 41]
[5]Dubber, Michael; Sperling, Oliver; Lindhorst, Thisbe K. [Organic and Biomolecular Chemistry, 2006, vol. 4, # 21, p. 3901 - 3912]

15
[ 116-11-0 ]
[ 7464-56-4 ]
allyl O²,O³;O⁴,O⁶-bis-isopropylidene-α-D-glucopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 20℃; for 2h;
76.6%	With toluene-4-sulfonic acid In acetone at 20℃; for 2h;

Reference： [1]Shieu, Jia-Cheng; Yeng-Jeng, Shaw; Luh, Tien-Yau [Journal of the Chinese Chemical Society, 2001, vol. 48, # 6 A, p. 1035 - 1040]
[2]Cheng, Wen-Lung; Shaw, Yeng-Jeng; Yeh, Sue-Min; Kanakamma, Puthuparampil P.; Chen, Yu-Huey; Chen, Chuo; Shieu, Jia-Cheng; Yiin, Shaang-Jyh; Lee, Gene-Hsiang; Wang, Yu; Luh, Tien-Yau [Journal of Organic Chemistry, 1999, vol. 64, # 2, p. 532 - 539]

16
[ 74808-10-9 ]
[ 7464-56-4 ]
Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-((2R,3S,4S,5R,6S)-6-allyloxy-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylsilyl trifluoromethanesulfonate In N,N-dimethyl-formamide at -42 - 20℃; for 3h;

Reference： [1]Zhu, Yuliang; Kong, Fanzuo [Synlett, 2000, # 5, p. 663 - 667]

17
[ 3282-30-2 ]
[ 7464-56-4 ]
[ 314252-91-0 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine at 0℃; for 2h;
	With pyridine at 0℃;

Reference： [1]Rosenberg, Heidi J.; Riley, Andrew M.; Correa, Vanessa; Taylor, Colin W.; Potter, Barry V.L. [Carbohydrate Research, 2000, vol. 329, # 1, p. 7 - 16]
[2]Wu, Changchun; Li, Yuxin; Liu, Ming; Liu, Jingbo; Hua, Xuewen; Zhang, Dongkai; Xiong, Lixia; Yang, Na; Wang, Baolei; Li, Zhengming [Chinese Journal of Chemistry, 2016, vol. 34, # 11, p. 1121 - 1128]

18
[ 98-59-9 ]
[ 7464-56-4 ]
[ 267900-42-5 ]

Yield	Reaction Conditions	Operation in experiment
83.8%	With pyridine; dmap
83.8%	With pyridine; dmap In water	4 2-3 3-4) Step d': Synthesis of 1-O-(2-propenyl)-6-O-(4-tolylsulfonyl)-α-D-glucose (V') Into 200 mL of anhydrous pyridine, 6.3 g (28.6 mmol) of 1-O-(2-propenyl)-α-D-glucose (IV') were dissolved, and 195 mg of DMAP and 7.0 g of p-toluenesulfonyl chloride were added. The solution was reacted for 16 hours at room temperature while stirring. Thereafter, the reaction was quenched by adding 20 mL of cold distilled water, and the reaction mixture was extracted with ethyl acetate (3200 mL). The organic layers were combined, acidified to pH 4 with 1.0 N and 0.1 N hydrochloric acids, washed with saturated aqueous sodium chloride (2200 mL), dried over anhydrous sodium sulfate, filtered, concentrated in vacuo, and purified by silica gel flash chromatography (dichloromethane:methanol=20:1) to give 8.6 g (24.0 mmol) of the title compound with yield of 83.8%.
83.8%	With pyridine; dmap In water	3.4 <Example 3: 3-4) Step d': Synthesis of 1-O-(2-propenyl)-6-O-(4-tolylsulfonyl)-α-D-glucose (V') Into 200 mL of anhydrous pyridine, 6.3 g (28.6 mmol) of 1-O-(2-propenyl)-α-D-glucose (IV') were dissolved, and 195 mg of DMAP and 7.0 g of p-toluenesulfonyl chloride were added. The solution was reacted for 16 hours at room temperature while stirring. Thereafter, the reaction was quenched by adding 20 mL of cold distilled water, and the reaction mixture was extracted with ethyl acetate (3200 mL). The organic layers were combined, acidified to pH 4 with 1.0 N and 0.1 N hydrochloric acids, washed with saturated aqueous sodium chloride (2200 mL), dried over anhydrous sodium sulfate, filtered, concentrated in vacuo, and purified by silica gel flash chromatography (dichloromethane:methanol=20:1) to give 8.6 g (24.0 mmol) of the title compound with yield of 83.8%.

83.8%

With pyridine; dmap at 20℃; for 16h;

1.6.C6 Route C6; 1-O-(2-propenyl)-6-O-(4-tolylsulfonyl)-α-D-glucose (6-4): The compound (6-3) (6.3 g, 28.6 mmol) was dissolved in dry pyridine (200 mL), and thereto were added p-dimethylaminopyridine (DMAP) (195 mg), and p-toluenesulfonyl chloride (7.0 g). While the solution was stirred, the reactive components were caused to react with each other at room temperature for 16 hours. Thereafter, thereto was added cold distilled water (20 mL) to terminate the reaction. The resultant was extracted with ethyl acetate (3 × 200 mL), and the organic layers were combined with each other. The combination was neutralized to a pH of 4 with 1.0 M hydrochloric acid and 0.1 M hydrochloric acid, washed with saturated saline (2 × 200 mL), dried over anhydrous sodium sulfate, filtrated, concentrated under reduced pressure, and then purified by silica gel flash chromatography (dichloromethane/methanol, 20:1) to yield the title compound (6-4) (8.6 mg (23.0 mmol), 83.8% yield).

Reference： [1]Hanashima, Shinya; Mizushina, Yoshiyuki; Yamazaki, Takayuki; Ohta, Keisuke; Takahashi, Syunya; Sahara, Hiroeki; Sakaguchi, Kengo; Sugawara, Fumio [Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 2, p. 367 - 376]
[2]Current Patent Assignee: TOYO SUISAN KAISHA LTD - US2002/52327, 2002, A1
[3]Current Patent Assignee: TOYO SUISAN KAISHA LTD - US6518410, 2003, B2
[4]Current Patent Assignee: TOYO SUISAN KAISHA LTD - EP2388264, 2011, A1 Location in patent: Page/Page column 40

19
1-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside [ No CAS ]
[ 7464-56-4 ]

Yield	Reaction Conditions	Operation in experiment
82.4%	With acetic acid at 80℃;

Reference： [1]Hanashima, Shinya; Mizushina, Yoshiyuki; Yamazaki, Takayuki; Ohta, Keisuke; Takahashi, Syunya; Sahara, Hiroeki; Sakaguchi, Kengo; Sugawara, Fumio [Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 2, p. 367 - 376]

20
[ 74808-10-9 ]
[ 7464-56-4 ]
[ 330960-33-3 ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylsilyl trifluoromethanesulfonate In N,N-dimethyl-formamide at -42 - 20℃; for 3h;

Reference： [1]Zhu, Yuliang; Kong, Fanzuo [Carbohydrate Research, 2001, vol. 332, # 1, p. 1 - 21]

21
[ 7464-56-4 ]
[ 80095-44-9 ]
Sulfuric acid mono-[(2R,3S,4R,5R,6S)-5-acetylamino-6-((2R,3S,4R,5R,6S)-6-allyloxy-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl] ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With β-N-acetylhexosaminidase from Aspergillus oryzae In phosphate buffer at 35℃; for 74h;

Reference： [1]Uzawa, Hirotaka; Zeng, Xiaoxiong; Minoura, Norihiko [Chemical Communications, 2003, # 1, p. 100 - 101]

22
[ 108-24-7 ]
[ 7464-56-4 ]
allyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With pyridine at 20℃;
	With pyridine; dmap
6.24 g	With pyridine; dmap at 20℃; for 10h;

Reference： [1]Hartmann, Mirja; Betz, Patrick; Sun, Yuchen; Gorb, Stanislav N.; Lindhorst, Thisbe K.; Krueger, Anke [Chemistry - A European Journal, 2012, vol. 18, # 21, p. 6485 - 6492]
[2]Wolfenden, Mark L.; Cloninger, Mary J. [Journal of the American Chemical Society, 2005, vol. 127, # 35, p. 12168 - 12169]
[3]Tsai, Charng-Sheng; Chen, Chao-Tsen [Collection of Czechoslovak Chemical Communications, 2012, vol. 77, # 4, p. 314 - 322]

23
[ 77-76-9 ]
[ 7464-56-4 ]
[ 721456-18-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 20℃; for 16h;

Reference： [1]Shiozaki, Masao; Doi, Hiromi; Tanaka, Daisuke; Shimozato, Takaichi; Kurakata, Shin-Ichi [Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 6, p. 1091 - 1104]

24
[ 7464-56-4 ]
p-nitrophenyl 2-acetamido-2-deoxy-6-O-sulfo-β-D-glucopyranoside, sodium salt [ No CAS ]
C₁₇H₂₈NO₁₄S^(1-)*Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With Aspergillus oryzae N-acetylhexosaminidase In phosphate buffer at 35℃; for 120h;

Reference： [1]Ogata, Makoto; Zeng, Xiaoxiong; Usui, Taichi; Uzawa, Hirotaka [Carbohydrate Research, 2007, vol. 342, # 1, p. 23 - 30]

25
[ 7464-56-4 ]
[ 920756-32-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium periodate In methanol; water at 0 - 25℃; for 3h;

Reference： [1]Anderluh, Marko [Tetrahedron Letters, 2006, vol. 47, # 52, p. 9203 - 9206]

26
[ 7464-56-4 ]
[ 721455-99-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 65 percent / p-TsOH*H₂O / dimethylformamide / 16 h / 20 °C 2: 98 percent / NaH / dimethylformamide / 16 h / 20 °C

Reference： [1]Shiozaki, Masao; Doi, Hiromi; Tanaka, Daisuke; Shimozato, Takaichi; Kurakata, Shin-Ichi [Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 6, p. 1091 - 1104]

27
[ 7464-56-4 ]
[ 721456-01-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 65 percent / p-TsOHH₂O / dimethylformamide / 16 h / 20 °C 2: 98 percent / NaH / dimethylformamide / 16 h / 20 °C 3: 54 percent / p-TsOHH₂O / methanol / 0.67 h / 20 °C 4: 100 percent / H₂ / Ir[(C₈H₁₂)(PMePh₂)2]PF₆ / tetrahydrofuran / 16 h / 20 °C

Reference： [1]Shiozaki, Masao; Doi, Hiromi; Tanaka, Daisuke; Shimozato, Takaichi; Kurakata, Shin-Ichi [Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 6, p. 1091 - 1104]

28
[ 7464-56-4 ]
[ 721456-00-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 65 percent / p-TsOHH₂O / dimethylformamide / 16 h / 20 °C 2: 98 percent / NaH / dimethylformamide / 16 h / 20 °C 3: 54 percent / p-TsOHH₂O / methanol / 0.67 h / 20 °C

Reference： [1]Shiozaki, Masao; Doi, Hiromi; Tanaka, Daisuke; Shimozato, Takaichi; Kurakata, Shin-Ichi [Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 6, p. 1091 - 1104]

29
[ 7464-56-4 ]
4-O-allyloxycarbonyl-2,3-di-O-dodecyl-D-glucopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 65 percent / p-TsOHH₂O / dimethylformamide / 16 h / 20 °C 2.1: 98 percent / NaH / dimethylformamide / 16 h / 20 °C 3.1: 54 percent / p-TsOHH₂O / methanol / 0.67 h / 20 °C 4.1: 100 percent / H₂ / Ir[(C₈H₁₂)(PMePh₂)2]PF₆ / tetrahydrofuran / 16 h / 20 °C 5.1: 95 percent / DMAP / CH₂Cl₂ / 16 h / 20 °C 6.1: pyridine / toluene / 0.17 h / 0 °C 6.2: 100 percent / toluene / 1 h / 0 °C 7.1: 74 percent / aq. HF / CH₂Cl₂; acetonitrile / 16 h / 20 °C

Reference： [1]Shiozaki, Masao; Doi, Hiromi; Tanaka, Daisuke; Shimozato, Takaichi; Kurakata, Shin-Ichi [Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 6, p. 1091 - 1104]

30
[ 7464-56-4 ]
[ 721456-02-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 65 percent / p-TsOHH₂O / dimethylformamide / 16 h / 20 °C 2: 98 percent / NaH / dimethylformamide / 16 h / 20 °C 3: 54 percent / p-TsOHH₂O / methanol / 0.67 h / 20 °C 4: 100 percent / H₂ / Ir[(C₈H₁₂)(PMePh₂)2]PF₆ / tetrahydrofuran / 16 h / 20 °C 5: 95 percent / DMAP / CH₂Cl₂ / 16 h / 20 °C

Reference： [1]Shiozaki, Masao; Doi, Hiromi; Tanaka, Daisuke; Shimozato, Takaichi; Kurakata, Shin-Ichi [Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 6, p. 1091 - 1104]

31
[ 7464-56-4 ]
[ 721456-03-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 65 percent / p-TsOHH₂O / dimethylformamide / 16 h / 20 °C 2.1: 98 percent / NaH / dimethylformamide / 16 h / 20 °C 3.1: 54 percent / p-TsOHH₂O / methanol / 0.67 h / 20 °C 4.1: 100 percent / H₂ / Ir[(C₈H₁₂)(PMePh₂)2]PF₆ / tetrahydrofuran / 16 h / 20 °C 5.1: 95 percent / DMAP / CH₂Cl₂ / 16 h / 20 °C 6.1: pyridine / toluene / 0.17 h / 0 °C 6.2: 100 percent / toluene / 1 h / 0 °C

Reference： [1]Shiozaki, Masao; Doi, Hiromi; Tanaka, Daisuke; Shimozato, Takaichi; Kurakata, Shin-Ichi [Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 6, p. 1091 - 1104]

32
[ 7464-56-4 ]
Carbonic acid allyl ester (2R,3R,4S,5R)-2-[(2R,3R,4R,5S,6R)-3-amino-5-(bis-allyloxy-phosphoryloxy)-4-((R)-3-methoxy-decyloxy)-6-methoxymethyl-tetrahydro-pyran-2-yloxymethyl]-4,5-bis-dodecyloxy-6-hydroxy-tetrahydro-pyran-3-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 65 percent / p-TsOHH₂O / dimethylformamide / 16 h / 20 °C 2.1: 98 percent / NaH / dimethylformamide / 16 h / 20 °C 3.1: 54 percent / p-TsOHH₂O / methanol / 0.67 h / 20 °C 4.1: 100 percent / H₂ / Ir[(C₈H₁₂)(PMePh₂)2]PF₆ / tetrahydrofuran / 16 h / 20 °C 5.1: 95 percent / DMAP / CH₂Cl₂ / 16 h / 20 °C 6.1: pyridine / toluene / 0.17 h / 0 °C 6.2: 100 percent / toluene / 1 h / 0 °C 7.1: 74 percent / aq. HF / CH₂Cl₂; acetonitrile / 16 h / 20 °C 8.1: 96 percent / AgOTf; TMSOTf / CH₂Cl₂ / 16 h / 20 °C 9.1: AcOH; Zn / tetrahydrofuran / 2.5 h / 25 °C

Reference： [1]Shiozaki, Masao; Doi, Hiromi; Tanaka, Daisuke; Shimozato, Takaichi; Kurakata, Shin-Ichi [Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 6, p. 1091 - 1104]

33
[ 7464-56-4 ]
4-O-allyloxycarbonyl-2,3-di-O-dodecyl-6-O-{2-deoxy-4-O-diallylphosphono-3-O-[(R)-3-(methoxy)decyl]-6-O-methyl-2-[(2,2,2-trichloroethoxycarbonyl)amino]-β-D-glucopyranosyl}-D-glucopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: 65 percent / p-TsOHH₂O / dimethylformamide / 16 h / 20 °C 2.1: 98 percent / NaH / dimethylformamide / 16 h / 20 °C 3.1: 54 percent / p-TsOHH₂O / methanol / 0.67 h / 20 °C 4.1: 100 percent / H₂ / Ir[(C₈H₁₂)(PMePh₂)2]PF₆ / tetrahydrofuran / 16 h / 20 °C 5.1: 95 percent / DMAP / CH₂Cl₂ / 16 h / 20 °C 6.1: pyridine / toluene / 0.17 h / 0 °C 6.2: 100 percent / toluene / 1 h / 0 °C 7.1: 74 percent / aq. HF / CH₂Cl₂; acetonitrile / 16 h / 20 °C 8.1: 96 percent / AgOTf; TMSOTf / CH₂Cl₂ / 16 h / 20 °C

Reference： [1]Shiozaki, Masao; Doi, Hiromi; Tanaka, Daisuke; Shimozato, Takaichi; Kurakata, Shin-Ichi [Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 6, p. 1091 - 1104]

34
[ 7464-56-4 ]
4-O-allyloxycarbonyl-6-O-{2-deoxy-4-O-diallylphosphono-3-O-[(R)-3-(methoxy)decyl]-6-O-methyl-2-[(Z)-(11-octadecenoyl)amino]-β-D-glucopyranosyl}-2,3-di-O-dodecyl-D-glucopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: 65 percent / p-TsOHH₂O / dimethylformamide / 16 h / 20 °C 2.1: 98 percent / NaH / dimethylformamide / 16 h / 20 °C 3.1: 54 percent / p-TsOHH₂O / methanol / 0.67 h / 20 °C 4.1: 100 percent / H₂ / Ir[(C₈H₁₂)(PMePh₂)2]PF₆ / tetrahydrofuran / 16 h / 20 °C 5.1: 95 percent / DMAP / CH₂Cl₂ / 16 h / 20 °C 6.1: pyridine / toluene / 0.17 h / 0 °C 6.2: 100 percent / toluene / 1 h / 0 °C 7.1: 74 percent / aq. HF / CH₂Cl₂; acetonitrile / 16 h / 20 °C 8.1: 96 percent / AgOTf; TMSOTf / CH₂Cl₂ / 16 h / 20 °C 9.1: AcOH; Zn / tetrahydrofuran / 2.5 h / 25 °C 10.1: 1.32 g / NaHCO₃ / tetrahydrofuran; H₂O / 1 h / 20 °C

Reference： [1]Shiozaki, Masao; Doi, Hiromi; Tanaka, Daisuke; Shimozato, Takaichi; Kurakata, Shin-Ichi [Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 6, p. 1091 - 1104]

35
[ 7464-56-4 ]
3-((2-aminoethyl)thio)propoxy 2,3,4,6-tetra-O-acetyl-2-α-D-glucopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: pyridine; DMAP 2: 74 percent / 1,1-di(tert-butylperoxy)cyclohexane / toluene / 4 h / 110 °C 3: TFA / CH₂Cl₂ / 12 h
	Multi-step reaction with 2 steps 1: dmap; pyridine / 10 h / 20 °C 2: methanol / 5 h / Irradiation; Inert atmosphere

Reference： [1]Wolfenden, Mark L.; Cloninger, Mary J. [Journal of the American Chemical Society, 2005, vol. 127, # 35, p. 12168 - 12169]
[2]Tsai, Charng-Sheng; Chen, Chao-Tsen [Collection of Czechoslovak Chemical Communications, 2012, vol. 77, # 4, p. 314 - 322]

36
[ 7464-56-4 ]
1-O-(6-isothiocyanato-4-thiohexyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: pyridine; DMAP 2: 74 percent / 1,1-di(tert-butylperoxy)cyclohexane / toluene / 4 h / 110 °C 3: TFA / CH₂Cl₂ / 12 h 4: 0.3 g / Et₃N / CH₂Cl₂ / 2 h

Reference： [1]Wolfenden, Mark L.; Cloninger, Mary J. [Journal of the American Chemical Society, 2005, vol. 127, # 35, p. 12168 - 12169]

37
[ 7464-56-4 ]
[ 866415-67-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine; DMAP 2: 74 percent / 1,1-di(tert-butylperoxy)cyclohexane / toluene / 4 h / 110 °C

Reference： [1]Wolfenden, Mark L.; Cloninger, Mary J. [Journal of the American Chemical Society, 2005, vol. 127, # 35, p. 12168 - 12169]

38
[ 7464-56-4 ]
[ 95451-96-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 0.85 g / methanesulfonic acid / dimethylformamide / 20 °C 2: pyridine / CH₂Cl₂ / 0.5 h / -25 °C 3: 0.620 g / n-BuNN₃ / dimethylformamide / 20 - 40 °C 4: 0.9513 g / acetic acid / H₂O / 0.25 h / 95 °C 5: 681.2 mg / sodium hydride / dimethylformamide / 1.25 h / 0 - 20 °C

Reference： [1]Koto, Shinkiti; Shinoda, Yoshika; Hirooka, Motoko; Sekino, Akiko; Ishizumi, Sachiko; Koma, Mutsuko; Matuura, Chieko; Sakata, Naoko [Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 8, p. 1603 - 1615]

39
[ 7464-56-4 ]
[ 95451-95-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 0.85 g / methanesulfonic acid / dimethylformamide / 20 °C 2: pyridine / CH₂Cl₂ / 0.5 h / -25 °C 3: 0.620 g / n-BuNN₃ / dimethylformamide / 20 - 40 °C 4: 0.9513 g / acetic acid / H₂O / 0.25 h / 95 °C

Reference： [1]Koto, Shinkiti; Shinoda, Yoshika; Hirooka, Motoko; Sekino, Akiko; Ishizumi, Sachiko; Koma, Mutsuko; Matuura, Chieko; Sakata, Naoko [Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 8, p. 1603 - 1615]

40
[ 7464-56-4 ]
[ 148968-89-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 0.85 g / methanesulfonic acid / dimethylformamide / 20 °C 2: pyridine / CH₂Cl₂ / 0.5 h / -25 °C 3: 0.620 g / n-BuNN₃ / dimethylformamide / 20 - 40 °C 4: 0.9513 g / acetic acid / H₂O / 0.25 h / 95 °C 5: 681.2 mg / sodium hydride / dimethylformamide / 1.25 h / 0 - 20 °C 6: 149.0 mg / NaOAc; PdCl₂; acetic acid / H₂O / 20 °C

Reference： [1]Koto, Shinkiti; Shinoda, Yoshika; Hirooka, Motoko; Sekino, Akiko; Ishizumi, Sachiko; Koma, Mutsuko; Matuura, Chieko; Sakata, Naoko [Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 8, p. 1603 - 1615]

41
[ 7464-56-4 ]
[ 612500-05-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 0.85 g / methanesulfonic acid / dimethylformamide / 20 °C 2: pyridine / CH₂Cl₂ / 0.5 h / -25 °C 3: 0.620 g / n-BuNN₃ / dimethylformamide / 20 - 40 °C

Reference： [1]Koto, Shinkiti; Shinoda, Yoshika; Hirooka, Motoko; Sekino, Akiko; Ishizumi, Sachiko; Koma, Mutsuko; Matuura, Chieko; Sakata, Naoko [Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 8, p. 1603 - 1615]

42
[ 7464-56-4 ]
Trifluoro-methanesulfonic acid (4aR,6S,7S,8S,8aS)-6-allyloxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 0.85 g / methanesulfonic acid / dimethylformamide / 20 °C 2: pyridine / CH₂Cl₂ / 0.5 h / -25 °C

Reference： [1]Koto, Shinkiti; Shinoda, Yoshika; Hirooka, Motoko; Sekino, Akiko; Ishizumi, Sachiko; Koma, Mutsuko; Matuura, Chieko; Sakata, Naoko [Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 8, p. 1603 - 1615]

43
[ 7464-56-4 ]
O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 0.85 g / methanesulfonic acid / dimethylformamide / 20 °C 2: pyridine / CH₂Cl₂ / 0.5 h / -25 °C 3: 0.620 g / n-BuNN₃ / dimethylformamide / 20 - 40 °C 4: 0.9513 g / acetic acid / H₂O / 0.25 h / 95 °C 5: 681.2 mg / sodium hydride / dimethylformamide / 1.25 h / 0 - 20 °C 6: 149.0 mg / NaOAc; PdCl₂; acetic acid / H₂O / 20 °C 7: 25 percent / p-nitrobenzenesulfonylchloride; triethylamine; silver(I) triflate / various solvent(s) 8: PdCl₂; NaOAc; acetic acid / H₂O / 20 °C

Reference： [1]Koto, Shinkiti; Shinoda, Yoshika; Hirooka, Motoko; Sekino, Akiko; Ishizumi, Sachiko; Koma, Mutsuko; Matuura, Chieko; Sakata, Naoko [Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 8, p. 1603 - 1615]

44
[ 7464-56-4 ]
O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-galactopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 0.85 g / methanesulfonic acid / dimethylformamide / 20 °C 2: pyridine / CH₂Cl₂ / 0.5 h / -25 °C 3: 0.620 g / n-BuNN₃ / dimethylformamide / 20 - 40 °C 4: 0.9513 g / acetic acid / H₂O / 0.25 h / 95 °C 5: 681.2 mg / sodium hydride / dimethylformamide / 1.25 h / 0 - 20 °C 6: 149.0 mg / NaOAc; PdCl₂; acetic acid / H₂O / 20 °C 7: 25 percent / p-nitrobenzenesulfonylchloride; triethylamine; silver(I) triflate / various solvent(s) 8: PdCl₂; NaOAc; acetic acid / H₂O / 20 °C

Reference： [1]Koto, Shinkiti; Shinoda, Yoshika; Hirooka, Motoko; Sekino, Akiko; Ishizumi, Sachiko; Koma, Mutsuko; Matuura, Chieko; Sakata, Naoko [Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 8, p. 1603 - 1615]

45
[ 7464-56-4 ]
[ 612499-96-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 0.85 g / methanesulfonic acid / dimethylformamide / 20 °C 2: pyridine / CH₂Cl₂ / 0.5 h / -25 °C 3: 0.620 g / n-BuNN₃ / dimethylformamide / 20 - 40 °C 4: 0.9513 g / acetic acid / H₂O / 0.25 h / 95 °C 5: 681.2 mg / sodium hydride / dimethylformamide / 1.25 h / 0 - 20 °C 6: 149.0 mg / NaOAc; PdCl₂; acetic acid / H₂O / 20 °C 7: 25 percent / p-nitrobenzenesulfonylchloride; triethylamine; silver(I) triflate / various solvent(s)

Reference： [1]Koto, Shinkiti; Shinoda, Yoshika; Hirooka, Motoko; Sekino, Akiko; Ishizumi, Sachiko; Koma, Mutsuko; Matuura, Chieko; Sakata, Naoko [Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 8, p. 1603 - 1615]

46
[ 7464-56-4 ]
allyl O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-galactopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 0.85 g / methanesulfonic acid / dimethylformamide / 20 °C 2: pyridine / CH₂Cl₂ / 0.5 h / -25 °C 3: 0.620 g / n-BuNN₃ / dimethylformamide / 20 - 40 °C 4: 0.9513 g / acetic acid / H₂O / 0.25 h / 95 °C 5: 681.2 mg / sodium hydride / dimethylformamide / 1.25 h / 0 - 20 °C 6: 149.0 mg / NaOAc; PdCl₂; acetic acid / H₂O / 20 °C 7: 66 percent / p-nitrobenzenesulfonylchloride; triethylamine; silver(I) triflate / various solvent(s)

Reference： [1]Koto, Shinkiti; Shinoda, Yoshika; Hirooka, Motoko; Sekino, Akiko; Ishizumi, Sachiko; Koma, Mutsuko; Matuura, Chieko; Sakata, Naoko [Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 8, p. 1603 - 1615]

47
[ 7464-56-4 ]
[ 340964-46-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: DMAP; pyridine / 16 h / 80 °C 2: imidazole / dimethylformamide / 6 h / 20 °C 3: pyridine / 24 h / 50 °C 4: 92 percent / TFA / H₂O / 2 h / 20 °C
	Multi-step reaction with 4 steps 1: DMAP; pyridine / 16 h / 80 °C 2: imidazole / dimethylformamide / 6 h / 20 °C 3: pyridine / 24 h / 50 °C 4: 49 percent / FeCl₃*6H₂O / CH₂Cl₂ / 2 h / 20 °C

Reference： [1]Zhang, Meimei; Du, Yuguo; Kong, Fanzuo [Carbohydrate Research, 2001, vol. 330, # 3, p. 319 - 324]
[2]Zhang, Meimei; Du, Yuguo; Kong, Fanzuo [Carbohydrate Research, 2001, vol. 330, # 3, p. 319 - 324]

48
[ 7464-56-4 ]
[ 340964-54-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: DMAP; pyridine / 16 h / 80 °C 2: imidazole / dimethylformamide / 6 h / 20 °C 3: pyridine / 24 h / 50 °C 4: 92 percent / TFA / H₂O / 2 h / 20 °C 5: 72.5 percent / Me₃SiOTf / CH₂Cl₂ / 1 h / -15 °C
	Multi-step reaction with 5 steps 1: DMAP; pyridine / 16 h / 80 °C 2: imidazole / dimethylformamide / 6 h / 20 °C 3: pyridine / 24 h / 50 °C 4: 49 percent / FeCl₃*6H₂O / CH₂Cl₂ / 2 h / 20 °C 5: 72.5 percent / Me₃SiOTf / CH₂Cl₂ / 1 h / -15 °C

Reference： [1]Zhang, Meimei; Du, Yuguo; Kong, Fanzuo [Carbohydrate Research, 2001, vol. 330, # 3, p. 319 - 324]
[2]Zhang, Meimei; Du, Yuguo; Kong, Fanzuo [Carbohydrate Research, 2001, vol. 330, # 3, p. 319 - 324]

49
[ 7464-56-4 ]
allyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->6)-2-O-acetyl-3,4-di-O-benzoyl-α-D-glucopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: DMAP; pyridine / 16 h / 80 °C 2: imidazole / dimethylformamide / 6 h / 20 °C 3: pyridine / 24 h / 50 °C 4: 92 percent / TFA / H₂O / 2 h / 20 °C 5: 72.5 percent / Me₃SiOTf / CH₂Cl₂ / 1 h / -15 °C 6: pyridine / 20 °C
	Multi-step reaction with 6 steps 1: DMAP; pyridine / 16 h / 80 °C 2: imidazole / dimethylformamide / 6 h / 20 °C 3: pyridine / 24 h / 50 °C 4: 49 percent / FeCl₃*6H₂O / CH₂Cl₂ / 2 h / 20 °C 5: 72.5 percent / Me₃SiOTf / CH₂Cl₂ / 1 h / -15 °C 6: pyridine / 20 °C

Reference： [1]Zhang, Meimei; Du, Yuguo; Kong, Fanzuo [Carbohydrate Research, 2001, vol. 330, # 3, p. 319 - 324]
[2]Zhang, Meimei; Du, Yuguo; Kong, Fanzuo [Carbohydrate Research, 2001, vol. 330, # 3, p. 319 - 324]

50
[ 7464-56-4 ]
[ 265312-94-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 83.8 percent / pyridine; DMAP 2: 91.6 percent / 2,6-lutidine / CH₂Cl₂ / 5 h / 0 °C 3: 82 percent / hexamethylphosphoric acid triamide / 3 h / 70 °C
	Multi-step reaction with 3 steps 1: dmap; pyridine / 16 h / 20 °C 2: 2,6-dimethylpyridine / dichloromethane / 16 h / Inert atmosphere 3: ethanol / 3 h / Reflux

Reference： [1]Hanashima, Shinya; Mizushina, Yoshiyuki; Yamazaki, Takayuki; Ohta, Keisuke; Takahashi, Syunya; Sahara, Hiroeki; Sakaguchi, Kengo; Sugawara, Fumio [Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 2, p. 367 - 376]
[2]Current Patent Assignee: TOYO SUISAN KAISHA LTD - EP2388264, 2011, A1

51
[ 7464-56-4 ]
[ 265312-96-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 83.8 percent / pyridine; DMAP 2: 91.6 percent / 2,6-lutidine / CH₂Cl₂ / 5 h / 0 °C 3: 82 percent / hexamethylphosphoric acid triamide / 3 h / 70 °C 4: 88 percent / OsO₄; trimethylamine N-oxide / 2-methyl-propan-2-ol; H₂O / 48 h / 20 °C
	Multi-step reaction with 4 steps 1: dmap; pyridine / 16 h / 20 °C 2: 2,6-dimethylpyridine / dichloromethane / 16 h / Inert atmosphere 3: ethanol / 3 h / Reflux 4: trimethylamine-N-oxide; water / osmium(VIII) oxide / <i>tert</i>-butyl alcohol / 22 h / 20 °C

Reference： [1]Hanashima, Shinya; Mizushina, Yoshiyuki; Yamazaki, Takayuki; Ohta, Keisuke; Takahashi, Syunya; Sahara, Hiroeki; Sakaguchi, Kengo; Sugawara, Fumio [Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 2, p. 367 - 376]
[2]Current Patent Assignee: TOYO SUISAN KAISHA LTD - EP2388264, 2011, A1

52
[ 7464-56-4 ]
[ 265312-92-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 83.8 percent / pyridine; DMAP 2: 91.6 percent / 2,6-lutidine / CH₂Cl₂ / 5 h / 0 °C
	Multi-step reaction with 2 steps 1: dmap; pyridine / 16 h / 20 °C 2: 2,6-dimethylpyridine / dichloromethane / 16 h / Inert atmosphere

Reference： [1]Hanashima, Shinya; Mizushina, Yoshiyuki; Yamazaki, Takayuki; Ohta, Keisuke; Takahashi, Syunya; Sahara, Hiroeki; Sakaguchi, Kengo; Sugawara, Fumio [Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 2, p. 367 - 376]
[2]Current Patent Assignee: TOYO SUISAN KAISHA LTD - EP2388264, 2011, A1

53
[ 7464-56-4 ]
[ 169822-03-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: pyridine / 2 h / 0 °C 2: p-toluenesulfonic acid / tetrahydrofuran / 2 h / 20 °C 3: NaOH / methanol / 1 h / Heating 4: NaH / dimethylformamide / 1.5 h / 0 - 20 °C 5: 1M HCl / 0.5 h
	Multi-step reaction with 4 steps 1: pyridine / 0 °C 2: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C 3: sodium hydroxide / methanol / Reflux 4: hydrogenchloride / methanol / 20 °C

Reference： [1]Rosenberg, Heidi J.; Riley, Andrew M.; Correa, Vanessa; Taylor, Colin W.; Potter, Barry V.L. [Carbohydrate Research, 2000, vol. 329, # 1, p. 7 - 16]
[2]Wu, Changchun; Li, Yuxin; Liu, Ming; Liu, Jingbo; Hua, Xuewen; Zhang, Dongkai; Xiong, Lixia; Yang, Na; Wang, Baolei; Li, Zhengming [Chinese Journal of Chemistry, 2016, vol. 34, # 11, p. 1121 - 1128]

54
[ 7464-56-4 ]
[ 169822-00-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: pyridine / 2 h / 0 °C 2: p-toluenesulfonic acid / tetrahydrofuran / 2 h / 20 °C 3: NaOH / methanol / 1 h / Heating 4: NaH / dimethylformamide / 1.5 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1: 1) dibutyltin oxide, 2) triethylamine / 1) toluene, reflux, 4 h, 2) toluene, 200-110 deg C, 2 d 2: 71 percent / p-toluenesulfonic acid / acetone / 0.08 h / Ambient temperature
	Multi-step reaction with 3 steps 1: pyridine / 0 °C 2: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C 3: sodium hydroxide / methanol / Reflux

Reference： [1]Rosenberg, Heidi J.; Riley, Andrew M.; Correa, Vanessa; Taylor, Colin W.; Potter, Barry V.L. [Carbohydrate Research, 2000, vol. 329, # 1, p. 7 - 16]
[2]Jenkins, David J.; Potter, Barry V.L. [Carbohydrate Research, 1996, vol. 287, # 2, p. 169 - 182]
[3]Wu, Changchun; Li, Yuxin; Liu, Ming; Liu, Jingbo; Hua, Xuewen; Zhang, Dongkai; Xiong, Lixia; Yang, Na; Wang, Baolei; Li, Zhengming [Chinese Journal of Chemistry, 2016, vol. 34, # 11, p. 1121 - 1128]

55
[ 7464-56-4 ]
[ 181777-23-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: pyridine / 2 h / 0 °C 2: p-toluenesulfonic acid / tetrahydrofuran / 2 h / 20 °C 3: NaOH / methanol / 1 h / Heating 4: NaH / dimethylformamide / 1.5 h / 0 - 20 °C 5: 1M HCl / 0.5 h 6: 77 percent / NaH / dimethylformamide / 12 h / 20 °C
	Multi-step reaction with 2 steps 1: 1) dibutyltin oxide, 2) triethylamine / 1) toluene, reflux, 4 h, 2) toluene, 200-110 deg C, 2 d 2: 72 percent / NaH / dimethylformamide / 3 h / Ambient temperature

Reference： [1]Rosenberg, Heidi J.; Riley, Andrew M.; Correa, Vanessa; Taylor, Colin W.; Potter, Barry V.L. [Carbohydrate Research, 2000, vol. 329, # 1, p. 7 - 16]
[2]Jenkins, David J.; Potter, Barry V.L. [Carbohydrate Research, 1996, vol. 287, # 2, p. 169 - 182]

56
[ 7464-56-4 ]
[ 314252-93-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine / 2 h / 0 °C 2: p-toluenesulfonic acid / tetrahydrofuran / 2 h / 20 °C
	Multi-step reaction with 2 steps 1: pyridine / 0 °C 2: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C

Reference： [1]Rosenberg, Heidi J.; Riley, Andrew M.; Correa, Vanessa; Taylor, Colin W.; Potter, Barry V.L. [Carbohydrate Research, 2000, vol. 329, # 1, p. 7 - 16]
[2]Wu, Changchun; Li, Yuxin; Liu, Ming; Liu, Jingbo; Hua, Xuewen; Zhang, Dongkai; Xiong, Lixia; Yang, Na; Wang, Baolei; Li, Zhengming [Chinese Journal of Chemistry, 2016, vol. 34, # 11, p. 1121 - 1128]

57
[ 7464-56-4 ]
2,6-di-O-benzyl-3,4-di-O-(p-methoxybenzyl)-β-D-glucopyranosylmethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: pyridine / 2 h / 0 °C 2.1: p-toluenesulfonic acid / tetrahydrofuran / 2 h / 20 °C 3.1: NaOH / methanol / 1 h / Heating 4.1: NaH / dimethylformamide / 1.5 h / 0 - 20 °C 5.1: 1M HCl / 0.5 h 6.1: 77 percent / NaH / dimethylformamide / 12 h / 20 °C 7.1: 70.5 percent / PdCl₂; methanol / 3 h 8.1: 67 percent / oxalyl chloride; DMSO / CH₂Cl₂ / 0.33 h / -78 °C 9.1: 65.1 percent / pyridine / tetrahydrofuran / 1.5 h / -45 - 0 °C 10.1: 0.5M 9-BBN / tetrahydrofuran / 3 h / 0 °C 10.2: 58 percent / 5 percent aq KOH; 30 percent H₂O₂
	Multi-step reaction with 10 steps 1.1: pyridine / 2 h / 0 °C 2.1: p-toluenesulfonic acid / tetrahydrofuran / 2 h / 20 °C 3.1: NaOH / methanol / 1 h / Heating 4.1: NaH / dimethylformamide / 1.5 h / 0 - 20 °C 5.1: 1M HCl / 0.5 h 6.1: 77 percent / NaH / dimethylformamide / 12 h / 20 °C 7.1: 70.5 percent / PdCl₂; methanol / 3 h 8.1: 67 percent / oxalyl chloride; DMSO / CH₂Cl₂ / 0.33 h / -78 °C 9.1: 65.1 percent / pyridine / tetrahydrofuran / 1.5 h / -45 - 0 °C 10.1: 1.0M BH₃-THF / tetrahydrofuran / 2 h / 0 - 20 °C 10.2: 5 percent aq KOH; 30 percent H₂O₂ / 0.5 h

Reference： [1]Rosenberg, Heidi J.; Riley, Andrew M.; Correa, Vanessa; Taylor, Colin W.; Potter, Barry V.L. [Carbohydrate Research, 2000, vol. 329, # 1, p. 7 - 16]
[2]Rosenberg, Heidi J.; Riley, Andrew M.; Correa, Vanessa; Taylor, Colin W.; Potter, Barry V.L. [Carbohydrate Research, 2000, vol. 329, # 1, p. 7 - 16]

58
[ 7464-56-4 ]
[ 774164-62-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 76 percent / NaOH, TBABr / H₂O / 16 h / 35 °C 2: 97 percent / methanol / 4 h / Irradiation 3: Et₃N / dimethylformamide / 60 h / 50 °C
	Multi-step reaction with 2 steps 1: sodium hydride; tetrabutylammomium bromide 2: methanol / Irradiation

Reference： [1]Kieburg, Christoffer; Dubber, Michael; Lindhorst, Thisbe K. [Synlett, 1997, # 12, p. 1447 - 1449]
[2]Lindhorst, Thisbe K.; Dubber, Michael [Carbohydrate Research, 2015, vol. 403, p. 90 - 97]

59
[ 7464-56-4 ]
[ 78184-40-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 90 percent / pyridine / 23 degC, 12 h, 60 degC, 1 h 2: 85 percent / NaH, Bu₄NI / tetrahydrofuran / 23 degC, 10 min, reflux 24 h 3: 93 percent / BF₃*OEt₂, Et₃SiH / acetonitrile; CH₂Cl₂ / 0.17 h / 0 °C
	Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / acetonitrile / 4 h / 40 °C 2: sodium hydroxide / N,N-dimethyl-formamide / 24 h / 20 °C 3: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether; dichloromethane / 4 h / Reflux

Reference： [1]Hoos; Huixin; Vasella; Weiss [Helvetica Chimica Acta, 1996, vol. 79, # 7, p. 1757 - 1784]
[2]Ruike, Tatsushi; Kanai, Yoshihiro; Iwabata, Kazuki; Matsumoto, Yuki; Murata, Hiroshi; Ishima, Masahiro; Ohta, Keisuke; Oshige, Masahiko; Katsura, Shinji; Kuramochi, Koji; Kamisuki, Shinji; Sahara, Hiroeki; Miura, Masahiko; Sugawara, Fumio; Sakaguchi, Kengo [Xenobiotica, 2018, p. 1 - 17]

60
[ 7464-56-4 ]
[ 87326-31-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 69 percent / dimethyl sulfate / dimethylformamide / 18 h / Ambient temperature 2: 91 percent / NaH / tetrahydrofuran / 24 h / Heating
	Multi-step reaction with 2 steps 1: 70 percent / DMF-dimethyl sulphate / dimethylformamide / 18 h / Ambient temperature 2: 91 percent / NaH / tetrahydrofuran / 70 °C
	Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / acetonitrile / 4 h / 40 °C 2: sodium hydroxide / N,N-dimethyl-formamide / 24 h / 20 °C

Multi-step reaction with 2 steps 1.1: toluenesulfonic acid monohydrate / N,N-dimethyl-formamide; acetonitrile / 16 h / 0 - 40 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 - 20 °C 2.2: 1 h / 0 - 20 °C

Reference： [1]Kanakamma, Puthuparampil P.; Mani, Neelakandha, S.; Maitra, Uday; Nair, Vijay [Journal of the Chemical Society. Perkin transactions I, 1995, # 18, p. 2339 - 2344]
[2]Mani, Neelakandha S.; Kanakamma, Puthuparambil P. [Tetrahedron Letters, 1994, vol. 35, # 21, p. 3629 - 3632]
[3]Ruike, Tatsushi; Kanai, Yoshihiro; Iwabata, Kazuki; Matsumoto, Yuki; Murata, Hiroshi; Ishima, Masahiro; Ohta, Keisuke; Oshige, Masahiko; Katsura, Shinji; Kuramochi, Koji; Kamisuki, Shinji; Sahara, Hiroeki; Miura, Masahiko; Sugawara, Fumio; Sakaguchi, Kengo [Xenobiotica, 2018, p. 1 - 17]
[4]Current Patent Assignee: GUNMA UNIVERSITY; M T 3 - JP6903273, 2021, B1

61
[ 7464-56-4 ]
[ 157399-20-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 69 percent / dimethyl sulfate / dimethylformamide / 18 h / Ambient temperature 2: 91 percent / NaH / tetrahydrofuran / 24 h / Heating 3: 80 percent / NaCNBH₃, HCl / diethyl ether; tetrahydrofuran / 0.17 h / Ambient temperature 4: NaH / tetrahydrofuran / 0.5 h / 70 °C
	Multi-step reaction with 4 steps 1: 70 percent / DMF-dimethyl sulphate / dimethylformamide / 18 h / Ambient temperature 2: 91 percent / NaH / tetrahydrofuran / 70 °C 3: 80 percent / NaCNBH₃-HCl / diethyl ether; tetrahydrofuran / 0.17 h / Ambient temperature 4: 98 percent / NaH / tetrahydrofuran / 5 h / 70 °C

Reference： [1]Kanakamma, Puthuparampil P.; Mani, Neelakandha, S.; Maitra, Uday; Nair, Vijay [Journal of the Chemical Society. Perkin transactions I, 1995, # 18, p. 2339 - 2344]
[2]Mani, Neelakandha S.; Kanakamma, Puthuparambil P. [Tetrahedron Letters, 1994, vol. 35, # 21, p. 3629 - 3632]

62
[ 7464-56-4 ]
[ 157399-21-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 69 percent / dimethyl sulfate / dimethylformamide / 18 h / Ambient temperature 2: 91 percent / NaH / tetrahydrofuran / 24 h / Heating 3: 80 percent / NaCNBH₃, HCl / diethyl ether; tetrahydrofuran / 0.17 h / Ambient temperature 4: NaH / tetrahydrofuran / 0.5 h / 70 °C 5: 1) O₃, 2) NaBH₄ / 1) MeOH, -78 deg C, 2) -78 deg C -> room temperature, 12 h
	Multi-step reaction with 5 steps 1: 70 percent / DMF-dimethyl sulphate / dimethylformamide / 18 h / Ambient temperature 2: 91 percent / NaH / tetrahydrofuran / 70 °C 3: 80 percent / NaCNBH₃-HCl / diethyl ether; tetrahydrofuran / 0.17 h / Ambient temperature 4: 98 percent / NaH / tetrahydrofuran / 5 h / 70 °C 5: 1.) O₃; 2.) NaBH₄ / 1.) MeOH, -78 deg C; 2.) -78 deg C -> r.t.

Reference： [1]Kanakamma, Puthuparampil P.; Mani, Neelakandha, S.; Maitra, Uday; Nair, Vijay [Journal of the Chemical Society. Perkin transactions I, 1995, # 18, p. 2339 - 2344]
[2]Mani, Neelakandha S.; Kanakamma, Puthuparambil P. [Tetrahedron Letters, 1994, vol. 35, # 21, p. 3629 - 3632]

63
[ 7464-56-4 ]
[ 153097-69-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 69 percent / dimethyl sulfate / dimethylformamide / 18 h / Ambient temperature 2: 91 percent / NaH / tetrahydrofuran / 24 h / Heating 3: 80 percent / NaCNBH₃, HCl / diethyl ether; tetrahydrofuran / 0.17 h / Ambient temperature
	Multi-step reaction with 3 steps 1: 70 percent / DMF-dimethyl sulphate / dimethylformamide / 18 h / Ambient temperature 2: 91 percent / NaH / tetrahydrofuran / 70 °C 3: 80 percent / NaCNBH₃-HCl / diethyl ether; tetrahydrofuran / 0.17 h / Ambient temperature

Reference： [1]Kanakamma, Puthuparampil P.; Mani, Neelakandha, S.; Maitra, Uday; Nair, Vijay [Journal of the Chemical Society. Perkin transactions I, 1995, # 18, p. 2339 - 2344]
[2]Mani, Neelakandha S.; Kanakamma, Puthuparambil P. [Tetrahedron Letters, 1994, vol. 35, # 21, p. 3629 - 3632]

64
[ 7464-56-4 ]
[ 172164-28-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 69 percent / dimethyl sulfate / dimethylformamide / 18 h / Ambient temperature 2: 91 percent / NaH / tetrahydrofuran / 24 h / Heating 3: 80 percent / NaCNBH₃, HCl / diethyl ether; tetrahydrofuran / 0.17 h / Ambient temperature 4: NaH / tetrahydrofuran / 0.5 h / 70 °C 5: 1) O₃, 2) NaBH₄ / 1) MeOH, -78 deg C, 2) -78 deg C -> room temperature, 12 h 6: 33 percent / NaH / tetrahydrofuran / 24 h / 70 °C 7: 63 percent / H₂ / Pd/C / methanol; ethyl acetate / 12 h / 2068.6 Torr

Reference： [1]Kanakamma, Puthuparampil P.; Mani, Neelakandha, S.; Maitra, Uday; Nair, Vijay [Journal of the Chemical Society. Perkin transactions I, 1995, # 18, p. 2339 - 2344]

65
[ 7464-56-4 ]
[ 172164-29-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 69 percent / dimethyl sulfate / dimethylformamide / 18 h / Ambient temperature 2: 91 percent / NaH / tetrahydrofuran / 24 h / Heating 3: 80 percent / NaCNBH₃, HCl / diethyl ether; tetrahydrofuran / 0.17 h / Ambient temperature 4: NaH / tetrahydrofuran / 0.5 h / 70 °C 5: 1) O₃, 2) NaBH₄ / 1) MeOH, -78 deg C, 2) -78 deg C -> room temperature, 12 h 6: 34 percent / NaH / tetrahydrofuran / 24 h / 70 °C 7: 91 percent / H₂ / Pd/C / methanol; ethyl acetate / 8 h / 2068.6 Torr

Reference： [1]Kanakamma, Puthuparampil P.; Mani, Neelakandha, S.; Maitra, Uday; Nair, Vijay [Journal of the Chemical Society. Perkin transactions I, 1995, # 18, p. 2339 - 2344]

66
[ 7464-56-4 ]
[ 172164-30-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 69 percent / dimethyl sulfate / dimethylformamide / 18 h / Ambient temperature 2: 91 percent / NaH / tetrahydrofuran / 24 h / Heating 3: 80 percent / NaCNBH₃, HCl / diethyl ether; tetrahydrofuran / 0.17 h / Ambient temperature 4: NaH / tetrahydrofuran / 0.5 h / 70 °C 5: 1) O₃, 2) NaBH₄ / 1) MeOH, -78 deg C, 2) -78 deg C -> room temperature, 12 h 6: 29 percent / NaH / tetrahydrofuran / 24 h / 70 °C 7: 72 percent / H₂ / Pd/C / methanol; ethyl acetate / 10 h / 2068.6 Torr

Reference： [1]Kanakamma, Puthuparampil P.; Mani, Neelakandha, S.; Maitra, Uday; Nair, Vijay [Journal of the Chemical Society. Perkin transactions I, 1995, # 18, p. 2339 - 2344]

67
[ 7464-56-4 ]
Acetic acid (1R,15S,17R,18S,19R)-19-acetoxy-17-acetoxymethyl-2,5,8,11,14,16-hexaoxa-bicyclo[13.2.2]nonadec-18-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 69 percent / dimethyl sulfate / dimethylformamide / 18 h / Ambient temperature 2: 91 percent / NaH / tetrahydrofuran / 24 h / Heating 3: 80 percent / NaCNBH₃, HCl / diethyl ether; tetrahydrofuran / 0.17 h / Ambient temperature 4: NaH / tetrahydrofuran / 0.5 h / 70 °C 5: 1) O₃, 2) NaBH₄ / 1) MeOH, -78 deg C, 2) -78 deg C -> room temperature, 12 h 6: 33 percent / NaH / tetrahydrofuran / 24 h / 70 °C 7: 63 percent / H₂ / Pd/C / methanol; ethyl acetate / 12 h / 2068.6 Torr 8: 73 percent / pyridine / 5 h / 0 °C

Reference： [1]Kanakamma, Puthuparampil P.; Mani, Neelakandha, S.; Maitra, Uday; Nair, Vijay [Journal of the Chemical Society. Perkin transactions I, 1995, # 18, p. 2339 - 2344]

68
[ 7464-56-4 ]
Acetic acid (1R,18S,20R,21S,22R)-22-acetoxy-20-acetoxymethyl-2,5,8,11,14,17,19-heptaoxa-bicyclo[16.2.2]docos-21-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 69 percent / dimethyl sulfate / dimethylformamide / 18 h / Ambient temperature 2: 91 percent / NaH / tetrahydrofuran / 24 h / Heating 3: 80 percent / NaCNBH₃, HCl / diethyl ether; tetrahydrofuran / 0.17 h / Ambient temperature 4: NaH / tetrahydrofuran / 0.5 h / 70 °C 5: 1) O₃, 2) NaBH₄ / 1) MeOH, -78 deg C, 2) -78 deg C -> room temperature, 12 h 6: 34 percent / NaH / tetrahydrofuran / 24 h / 70 °C 7: 91 percent / H₂ / Pd/C / methanol; ethyl acetate / 8 h / 2068.6 Torr 8: 70 percent / pyridine / 5 h / 0 °C

Reference： [1]Kanakamma, Puthuparampil P.; Mani, Neelakandha, S.; Maitra, Uday; Nair, Vijay [Journal of the Chemical Society. Perkin transactions I, 1995, # 18, p. 2339 - 2344]

69
[ 7464-56-4 ]
Acetic acid (1R,22S,24R,25S,26R)-26-acetoxy-24-acetoxymethyl-2,5,8,15,18,21,23-heptaoxa-tricyclo[20.2.2.0^9,14]hexacosa-9,11,13-trien-25-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 69 percent / dimethyl sulfate / dimethylformamide / 18 h / Ambient temperature 2: 91 percent / NaH / tetrahydrofuran / 24 h / Heating 3: 80 percent / NaCNBH₃, HCl / diethyl ether; tetrahydrofuran / 0.17 h / Ambient temperature 4: NaH / tetrahydrofuran / 0.5 h / 70 °C 5: 1) O₃, 2) NaBH₄ / 1) MeOH, -78 deg C, 2) -78 deg C -> room temperature, 12 h 6: 29 percent / NaH / tetrahydrofuran / 24 h / 70 °C 7: 72 percent / H₂ / Pd/C / methanol; ethyl acetate / 10 h / 2068.6 Torr 8: 70 percent / pyridine / 5 h / 0 °C

Reference： [1]Kanakamma, Puthuparampil P.; Mani, Neelakandha, S.; Maitra, Uday; Nair, Vijay [Journal of the Chemical Society. Perkin transactions I, 1995, # 18, p. 2339 - 2344]

70
[ 7464-56-4 ]
(1R,20R,21S,22R)-21,22-Bis-benzyloxy-20-benzyloxymethyl-2,5,8,11,14,17,19-heptaoxa-bicyclo[16.2.2]docosane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 70 percent / DMF-dimethyl sulphate / dimethylformamide / 18 h / Ambient temperature 2: 91 percent / NaH / tetrahydrofuran / 70 °C 3: 80 percent / NaCNBH₃-HCl / diethyl ether; tetrahydrofuran / 0.17 h / Ambient temperature 4: 98 percent / NaH / tetrahydrofuran / 5 h / 70 °C 5: 1.) O₃; 2.) NaBH₄ / 1.) MeOH, -78 deg C; 2.) -78 deg C -> r.t. 6: 34 percent / NaH / tetrahydrofuran / 24 h / 70 °C

Reference： [1]Mani, Neelakandha S.; Kanakamma, Puthuparambil P. [Tetrahedron Letters, 1994, vol. 35, # 21, p. 3629 - 3632]

71
[ 7464-56-4 ]
(1R,24R,25S,26R)-25,26-Bis-benzyloxy-24-benzyloxymethyl-2,5,8,15,18,21,23-heptaoxa-tricyclo[20.2.2.0^9,14]hexacosa-9,11,13-triene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 70 percent / DMF-dimethyl sulphate / dimethylformamide / 18 h / Ambient temperature 2: 91 percent / NaH / tetrahydrofuran / 70 °C 3: 80 percent / NaCNBH₃-HCl / diethyl ether; tetrahydrofuran / 0.17 h / Ambient temperature 4: 98 percent / NaH / tetrahydrofuran / 5 h / 70 °C 5: 1.) O₃; 2.) NaBH₄ / 1.) MeOH, -78 deg C; 2.) -78 deg C -> r.t. 6: 29 percent / NaH / tetrahydrofuran / 24 h / 70 °C

Reference： [1]Mani, Neelakandha S.; Kanakamma, Puthuparambil P. [Tetrahedron Letters, 1994, vol. 35, # 21, p. 3629 - 3632]

72
[ 7464-56-4 ]
[ 122220-84-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 62 percent / NaH / 3 h / 100 °C 2: p-nitrobenzenesulfonyl chloride (NsCl), silver trifluoromethanesulfonate (AgOTf), Et₃N, N,N-dimethylacetamide (DMA) / CH₂Cl₂ 3: 1.) tris(triphenylphosphine)rhodium(I) chloride, 2.) aq. HCl / 1.) ethanol, benzene, H₂O, reflux, overnight, 2.) acetone, 50 deg C, 1 h

Reference： [1]Koto, Shinkiti; Morishima, Naohiko; Shichi, Sonoko; Haigoh, Hisamitsu; Hirooka, Motoko; et al. [Bulletin of the Chemical Society of Japan, 1992, vol. 65, # 12, p. 3257 - 3274]

73
[ 1122-58-3 ]
[ 98-59-9 ]
[ 7464-56-4 ]
[ 267900-42-5 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In water	1 Route p: 1-O-(2-propenyl)-6-O-(4-tolylsulfonyl)-α-D-glucose (V) Route p: 1-O-(2-propenyl)-6-O-(4-tolylsulfonyl)-α-D-glucose (V) Into 200 mL of anhydrous pyridine, 6.3 g (28.6 mmol) of the compound (IV) was dissolved, and 195 mg of p-dimethylaminopyridine (DMAP) and 7.0 g of p-toluenesulfonyl chloride were added. The solution was reacted for 16 hours at room temperature while stirring. Thereafter, the reaction was quenched by adding 20 mL of cold distilled water, and the reaction mixture was extracted with ethyl acetate (3200 ML). The organic layers were combined, neutralized to pH 4 with 1.0 M and 0.1 M hydrochloric acids, washed with brine (2200 mL), dried over anhydrous sodium sulfate, filtered, concentrated in vacuo, and purified by silica gel flash chromatography (dichloromethane:methanol=20:1) (yield: 8.6 mg (23.0 mmol), recovery: 83.8%). 1H NMR(300 MHz, CDCl3+TMS); 7.77(2H,d,J=8.3,Ar at TsCH3),7.30(2H, d, J=8.1 Ar at TsSO2), 5.90-5.77(1H, m, -C=CH2), 5.24(1H, dd, J=1.4&17.2, -CH=C2), 5.11(1H, dd, J=1.2&12.4, -CH=C2), 4.79(1H, d, J=3.3, H-1), 4.38-3.38(8H, m), 2.40(3H, s, TSC)

Reference： [1]Current Patent Assignee: TOYO SUISAN KAISHA LTD - US2002/28776, 2002, A1

74
aq. H₂ SO₄ [ No CAS ]
[ 7732-18-5 ]
[ 76-83-5 ]
[ 7464-56-4 ]
[ 107242-80-8 ]

Yield	Reaction Conditions	Operation in experiment
23.3 g (90%)	In pyridine; acetone	2 Preparation of 4-methylumbelliferyl(5R)-5-phosphonyl-β-D-xylopyranoside (16): STR9 Allyl 6-O-trityl-α-D-glucopyranoside (2). A solution of allyl α-D-glucopyranoside (1) (prepared according to R. E. Wing, J. N. BeMiller, Carbohydr. Res. 1969, 10, 441) (12.5 g, 56.8 mmol) and triphenylmethyl chloride (20.0 g, 71.7 mmol) in dry pyridine (120 ml) was stirred at r.t. for 12 h, and at 60° for 1 h. After the addition of triphenylmethyl chloride (12.0 g, 43.0 mmol), the solution was stirred at 60° until all starting material has disappeared (3-4 h). H2 O (120 ml) was added to the still warm solution. Extraction with EtOAc, extraction of the combined org. layers with 1M aq. H2 SO4 and brine, evaporation of the organic layer and FC (400 g SiO2, toluene/actone 2:1→toluene/acetone 1:1) gave 23.3 g (90%) of 2. Grey glassy solid.

Reference： [1]Current Patent Assignee: SANOFI - US5621002, 1997, A

75
[ 7464-56-4 ]
C₈H₁₆O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ozone In water-d2

Reference： [1]Fang, Tammy T.; Bendiak, Brad [Journal of the American Chemical Society, 2007, vol. 129, # 31, p. 9721 - 9736]

76
[ 13154-24-0 ]
[ 7464-56-4 ]
C₁₈H₃₆O₆Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 10h;

Reference： [1]Ban, Lan; Mrksich, Milan [Angewandte Chemie - International Edition, 2008, vol. 47, # 18, p. 3396 - 3399]

77
[ 33513-42-7 ]
[ 7464-56-4 ]
[ 1152233-54-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; Inert atmosphere; Stage #2: 1-O-allyl-α-D-glucopyranoside In N,N-dimethyl-formamide at 60℃; Inert atmosphere; Cooling; Stage #3: With water; sodium hydrogencarbonate In N,N-dimethyl-formamide

Reference： [1]Thota, Niranjan; Mukherjee, Debaraj; Reddy, Mallepally Venkat; Yousuf, Syed Khalid; Koul, Surrinder; Taneja, Subhash Chandra [Organic and Biomolecular Chemistry, 2009, vol. 7, # 7, p. 1280 - 1283]

78
[ 60-24-2 ]
[ 7464-56-4 ]
[ 1234565-41-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With 2,2'-azobis(isobutyronitrile) In 1,4-dioxane at 75℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Hassan, Hammed H.A.M. [Letters in Organic Chemistry, 2010, vol. 7, # 2, p. 127 - 135]

79
[ 142-62-1 ]
[ 7464-56-4 ]
[ 1260954-90-2 ]

Yield	Reaction Conditions	Operation in experiment
62%	With di-isopropyl azodicarboxylate; triphenylphosphine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;

Reference： [1]Schindler, Corinna S.; Bertschi, Louis; Carreira, Erick M. [Angewandte Chemie - International Edition, 2010, vol. 49, # 48, p. 9229 - 9232]

80
[ 7464-56-4 ]
[ 1234307-18-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: dmap; pyridine / 16 h / 20 °C 2: 2,6-dimethylpyridine / dichloromethane / 16 h / Inert atmosphere 3: ethanol / 3 h / Reflux 4: trimethylamine-N-oxide; water / osmium(VIII) oxide / <i>tert</i>-butyl alcohol / 22 h / 20 °C 5: pyridine / dichloromethane / 2 h / 20 °C

Reference： [1]Current Patent Assignee: TOYO SUISAN KAISHA LTD - EP2388264, 2011, A1

81
[ 7464-56-4 ]
[ 1234307-20-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: dmap; pyridine / 16 h / 20 °C 2: 2,6-dimethylpyridine / dichloromethane / 16 h / Inert atmosphere 3: ethanol / 3 h / Reflux 4: trimethylamine-N-oxide; water / osmium(VIII) oxide / <i>tert</i>-butyl alcohol / 22 h / 20 °C 5: pyridine / dichloromethane / 2 h / 20 °C 6: pyridine / dichloromethane / 2 h / 20 °C

Reference： [1]Current Patent Assignee: TOYO SUISAN KAISHA LTD - EP2388264, 2011, A1

82
[ 7464-56-4 ]
[ 1234307-22-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: dmap; pyridine / 16 h / 20 °C 2: 2,6-dimethylpyridine / dichloromethane / 16 h / Inert atmosphere 3: ethanol / 3 h / Reflux 4: trimethylamine-N-oxide; water / osmium(VIII) oxide / <i>tert</i>-butyl alcohol / 22 h / 20 °C 5: pyridine / dichloromethane / 2 h / 20 °C 6: pyridine / dichloromethane / 2 h / 20 °C 7: Oxone; potassium acetate; acetic acid / 48 h / 20 °C

Reference： [1]Current Patent Assignee: TOYO SUISAN KAISHA LTD - EP2388264, 2011, A1

83
[ 7464-56-4 ]
[ 1234307-23-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: dmap; pyridine / 16 h / 20 °C 2: 2,6-dimethylpyridine / dichloromethane / 16 h / Inert atmosphere 3: ethanol / 3 h / Reflux 4: trimethylamine-N-oxide; water / osmium(VIII) oxide / <i>tert</i>-butyl alcohol / 22 h / 20 °C 5: pyridine / dichloromethane / 2 h / 20 °C 6: pyridine / dichloromethane / 2 h / 20 °C 7: Oxone; potassium acetate; acetic acid / 48 h / 20 °C 8: trifluoroacetic acid; water; acetic acid / tetrahydrofuran / 48 h / 20 °C

Reference： [1]Current Patent Assignee: TOYO SUISAN KAISHA LTD - EP2388264, 2011, A1

84
[ 7464-56-4 ]
[ 1234307-24-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: dmap; pyridine / 16 h / 20 °C 2: 2,6-dimethylpyridine / dichloromethane / 16 h / Inert atmosphere 3: ethanol / 3 h / Reflux 4: trimethylamine-N-oxide; water / osmium(VIII) oxide / <i>tert</i>-butyl alcohol / 22 h / 20 °C 5: pyridine / dichloromethane / 2 h / 20 °C 6: dmap; 2,2'-dipyridyl carbonate / dichloromethane / 48 h / 20 °C

Reference： [1]Current Patent Assignee: TOYO SUISAN KAISHA LTD - EP2388264, 2011, A1

85
[ 7464-56-4 ]
[ 1234307-25-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: dmap; pyridine / 16 h / 20 °C 2: 2,6-dimethylpyridine / dichloromethane / 16 h / Inert atmosphere 3: ethanol / 3 h / Reflux 4: trimethylamine-N-oxide; water / osmium(VIII) oxide / <i>tert</i>-butyl alcohol / 22 h / 20 °C 5: pyridine / dichloromethane / 2 h / 20 °C 6: dmap; 2,2'-dipyridyl carbonate / dichloromethane / 48 h / 20 °C 7: Oxone; potassium acetate; acetic acid / 24 h / 20 °C

Reference： [1]Current Patent Assignee: TOYO SUISAN KAISHA LTD - EP2388264, 2011, A1

86
[ 7464-56-4 ]
[ 1234307-26-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: dmap; pyridine / 16 h / 20 °C 2: 2,6-dimethylpyridine / dichloromethane / 16 h / Inert atmosphere 3: ethanol / 3 h / Reflux 4: trimethylamine-N-oxide; water / osmium(VIII) oxide / <i>tert</i>-butyl alcohol / 22 h / 20 °C 5: pyridine / dichloromethane / 2 h / 20 °C 6: dmap; 2,2'-dipyridyl carbonate / dichloromethane / 48 h / 20 °C 7: Oxone; potassium acetate; acetic acid / 24 h / 20 °C 8: trifluoroacetic acid; water; acetic acid / tetrahydrofuran / 48 h / 20 °C

Reference： [1]Current Patent Assignee: TOYO SUISAN KAISHA LTD - EP2388264, 2011, A1

87
[ 93382-48-0 ]
[ 7464-56-4 ]

Yield	Reaction Conditions	Operation in experiment
82.4%	With water; acetic acid at 100℃; for 1h;	1.6.B6 Route B6; 1-O-(2-propenyl)-α-D-glucose (6-3): The compound (6-2) (10.7 g, 34.7 mmol) was dissolved in a solution (260 mL) of acetic acid and water (8:5), and the reactive components were caused to react with each other at 100°C for 1 hour. The solution was concentrated under reduced pressure, and purified by silica gel flash chromatography (dichloromethane/methanol, 6:1) to yield the title compound (6-3) (6.3 g (28.6 mmol), 82.4% yield).

Reference： [1]Current Patent Assignee: TOYO SUISAN KAISHA LTD - EP2388264, 2011, A1 Location in patent: Page/Page column 40

88
[ 1125-88-8 ]
[ 7464-56-4 ]
[ 93382-48-0 ]

Yield	Reaction Conditions	Operation in experiment
39%	With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 60℃; for 3h;	Allyl 4,6-O-Benzylidene-α-D-glucopyranoside²(6) The glycoside 5 (7.60 g, 34.5 mmol) was dissolved in anhyd DMF (60 mL), benzaldehyde dimethylacetal (1.6 mL, 11 mmol) and TsOH·H2O (10.6 mg, 0.0559 mmol) were added and the mixture was stirred at 60 °C for 3 h, poured into ice-cold sat.aq NaHCO3 (30 mL) and diluted with H2O (150 mL). The crude product was purified by flash column chromatography on silica (PE/ethyl acetate, 2:1) to yield a colourless solid. Yield: 4.2 g (39%); 1H NMR (400 MHz, CDCl3): δ 7.50 - 7.48 (m, 2H), 7.37 - 7.35 (m, 3H), 5.94 - 5.87 (m, 1H), 5.52 (s, 1H), 5.35 (d, J = 20.0 Hz, 1H), 5.26 (d, J = 12.1 Hz, 1H), 4.94 (d, J = 4.1Hz, 1H), 4.32-4.21 (m, 2H), 4.07-4.05 (m, 1H), 3.94 (t, J = 8.1 Hz, 1H), 3.87-3.81 (m, 1H), 3.75 (t, J = 8.1Hz , 1H), 3.63-3.60 (m, 1H), 3.51 (t, J = 20.0Hz, 1H), 2.97 (brs, 1H), 2.41 (brs, 1H) ppm. 13C NMR (101 MHz, CDCl3) δ 137.14, 133.41, 129.38, 128.46, 126.42, 118.45, 102.02, 97.99, 77.47, 77.16, 76.84, 72.95, 71.89, 68.99, 62.70 ppm. The spectroscopic data are in agreement with literature data.
	In acetonitrile at 20℃;	1 Crude allyl-D-glucopyranoside was dissolved in acetonitrile (1000 mL). To this stirred solution were added benzaldehyde dimethylacetal (250 mL, 1 .7 mol) and (+/-)-camphor-10-sulfonic acid (12 g, 0.05 mol) and the solution was stirred at room temperature overnight. The solids were filtered off, the solvent was removed in vacuo and the residue was taken up in ethyl acetate (1000 mL), washed with saturated NaHCO3 (3 x 200 mL) and water (3 x 200 mL) then evaporated to a thick syrup. The syrup was dissolved in hot ethanol (500 mL) and cooled to -20°C for 2.5 days. The solid product was filtered and washed with cold ethanol, and dried under vacuum to give allyl-4,6-0-benzylidene-α-D-glucopyranoside (150 g, 48%).
	With toluene-4-sulfonic acid In toluene at 20 - 50℃;

Reference： [1]Wang, Yanhui; Zhao, Xiaoke; Kong, Qiuyun; Yao, Jiajian; Meng, Xiangbao; Li, Zhongjun [Tetrahedron Letters, 2017, vol. 58, # 16, p. 1655 - 1658]
[2]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - WO2011/137181, 2011, A1 Location in patent: Page/Page column 36-37
[3]Koch, Stefan; Schollmeyer, Dieter; Löwe, Holger; Kunz, Horst [Chemistry - A European Journal, 2013, vol. 19, # 22, p. 7020 - 7041]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	7464-56-4	MDL No. :	MFCD04973540
Formula :	C₉H₁₆O₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XJNKZTHFPGIJNS-ZEBDFXRSSA-N
M.W :	220.22	Pubchem ID :	10878666
Synonyms :

Signal Word:	Warning	Class:
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Hazard Statements:	H302-H312-H332	Packing Group:
GHS Pictogram:

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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 7464-56-4 ] {[proInfo.proName]}

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[ 7464-56-4 ] Synthesis Path-Downstream 1~88

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