Name: 138-59-0|(3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-ene-1-carboxylic acid|98%
Brand: Ambeed
SKU: A134982
Price: 8.0 USD
Availability: InStock
Rating: 99 (35 reviews)

1
[ 908094-01-9 ]
[ 138-59-0 ]
[ 40983-58-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	In methanol; diethyl ether for 15h; Ambient temperature;
	In methanol
	In methanol; diethyl ether at -20 - -15℃;

	at 0℃;
	In tetrahydrofuran

Reference： [1]Zamir, Lolita O.; Luthe, Corinne [Canadian Journal of Chemistry, 1984, vol. 62, p. 1169 - 1175]
[2]Luthe, Corinne; Zamir, Lolita O. [Tetrahedron Letters, 1983, vol. 24, # 41, p. 4409 - 4412]
[3]Meier; Tamm [Helvetica Chimica Acta, 1991, vol. 74, # 4, p. 807 - 818]
[4]Kim; Kirschning; Bergon; Ahn; Wang; Shibuya; Floss [Journal of the American Chemical Society, 1992, vol. 114, # 12, p. 4941 - 4943]
[5]Pansegrau, Paul D.; Anderson, Karen S.; Widlanski, Theodore; Ream, Joel E.; Douglas Sammons; Sikorski, James A.; Knowles, Jeremy R. [Tetrahedron Letters, 1991, vol. 32, # 23, p. 2589 - 2592]
[6]Grewe; Bokranz [Chemische Berichte, 1955, vol. 88, p. 49,55] Fischer; Dangschat [Helvetica Chimica Acta, 1934, vol. 17, p. 1200,1201][Helvetica Chimica Acta, 1935, vol. 18, p. 1206,1207] Suami, Tetsuo; Tadano, Kin-ichi; Ueno, Yoshihide; Iimura, Youichi [Chemistry Letters, 1985, p. 37 - 40] Ulibarri, Gerardo; Nadler, William; Skrydstrup, Troels; Audrain, Helene; Chiaroni, Angele; et al. [Journal of Organic Chemistry, 1995, vol. 60, # 9, p. 2753 - 2761]

2
[ 67-56-1 ]
[ 138-59-0 ]
[ 40983-58-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With Amberlite IR 120 for 16h; Heating;
100%	With Amberlite-IR₁₂₀ at 65℃; for 18h;
100%	With hydrogenchloride at 60℃; for 6h;

100%	With hydrogenchloride at 60℃; for 4h;
100%	With hydrogenchloride at 60℃; for 6h;
100%	With dowex 50H+ Reflux;
100%	With sulfuric acid at 20℃; for 50h;	2; 2A (-)-Shikimic acid (20 g) in MeOH (200 ml) and sulfuric acid (2 ml, 98%) are stirred at rt for 50 h. The reaction mixture is neutralized with 2N aqueous NaOH in the cold. After evaporation to dryness, the residue is purified by silica gel chromatography to afford II (19.2 g).
98%	With hydrogenchloride at 60℃; for 4h;
96%	With camphor-10-sulfonic acid for 10h; Heating;
96%	With (1S)-10-camphorsulfonic acid for 10h; Heating;
96%	With (+) cation resin for 15h; Heating;
95%	With Amberlite IR 120 for 12h; Heating;
95%	With acetyl chloride at 0 - 20℃; Inert atmosphere;	1 Example 1: Preparation of Compound IV The shikimic acid (50g, 0.287mol) was dissolved in 500mL of dry methanol, cooled to 0 ° C under nitrogen, acetyl chloride (23.4g, 0.3mol) was naturally warmed to room temperature, the temperature was allowed to react until TLC disappeared , The reaction is completed.The reaction was quenched with water, extracted with ethyl acetate, the organic phases were combined, washed with brine and dried over anhydrous Na2SO4The crude product was dried and concentrated to give a pale yellow oil.The crude product was chromatographed on a silica gel column to give 54 g of Compound IV 51g as a light yellow oil in 95% yield.
93%	With thionyl chloride at 10℃;
93%	With thionyl chloride at 0 - 20℃;
92%	With oxone at 60℃;
91%	With thionyl chloride at 40℃; for 3h;
88%	With hydrogenchloride at 60℃; for 5h;
75%	With camphor-10-sulfonic acid Reflux;
	With hydrogenchloride
	With hydrogenchloride Heating; Yield given;
	With hydrogenchloride Heating; Yield given;
	With hydrogenchloride
	With sulfuric acid at 20℃; for 50h;	1 (-)-Shikimic acid (20 g) in MeOH (200 ml) and sulfuric acid (2 ml, 98%) are stirred at room temperature (rt) for 50 h. The reaction mixture is neutralized with 2N aqueous NaOH in the cold. After evaporation to dryness, the residue is purified by silica gel chromatography to afford II (19.2 g).
	With sulfuric acid at 20℃; for 50h;	4 Example 4; Synthesis of Glycomimetic (FIG. 3); Synthesis of intermediate II: (-)-Shikimic acid (20 g) in MeOH (200 ml) and sulfuric acid (2 ml, 98%) are stirred at rt for 50 h. The reaction mixture is neutralized with 2N aqueous NaOH in the cold. After evaporation to dryness, the residue is purified by silica gel chromatography to afford II (19.2 g).
	With thionyl chloride at 10 - 40℃; for 4h;
	With hydrogenchloride In water at 20℃; for 50h;	4 EXAMPLE 4; SYNTHESIS OF SECOND GLYCOMIMETIC (COMPOUND XX OF FIG.4); Synthesis of intermediate II:; (-)-Shikimic acid (20 g) in MeOH (200 ml) and concentrated hydrochloric acid (2 ml) are stirred at RT for 50 h. The reaction mixture is neutralized with 2N aqueous NaOH in the cold. After evaporation to dryness, the residue is purified by silica gel chromatography to afford II (19.2 g).
2.03 g	With thionyl chloride for 1.5h; Reflux;
	With p-TsOH/SiO₂ for 5h; Reflux;	2.1 Typical procedure for the preparation of 3-MDHS To a mixture of (-)-shikimic acid (8.7g, 0.05mol) and p-TsOH/SiO2 (1.4g) wasadded MeOH (100 ml). The mixture was heated at reflux for 5 h. After cooling, thecatalyst was filtered off and the filtrate was concentrated under reduced pressure togive crude (-)-methyl shikimate.
10.2 g	With sulfuric acid at 20℃; for 24h;	A Step A 3,4,5-trihydroxycyclohex-1-enecarboxylic acid methyl ester (formula a) Take 10.0 g (57.4 mmol) of shikimic acid,Add 100 mL of methanol to suspend,Add 2.0 mL of concentrated sulfuric acid,Stir the reaction at room temperature,The reaction solution gradually clarifies,24h reaction is over,Stop the reaction,Add sodium carbonate powder to the reaction solution under stirring to adjust the pH to neutral.filter,The filtrate was evaporated under reduced pressure to give a crude material.Column chromatography gave 10.2 g of solid 3,4,5-trihydroxycyclohex-1-enecarboxylic acid methyl ester (a).
	With Amberlyst 15 ion-exchange resin for 10h; Reflux; Large scale;

Reference： [1]Delfourne, Evelyne; Despeyroux, Pierre; Gorrichon, Liliane; Veronique, Jacqueline [Journal of Chemical Research, Miniprint, 1991, # 3, p. 532 - 544]
[2]Tan, Derek S.; Foley, Michael A.; Stockwell, Brent R.; Shair, Matthew D.; Schreiber, Stuart L. [Journal of the American Chemical Society, 1999, vol. 121, # 39, p. 9073 - 9087]
[3]Sanchez-Abella, Laura; Fernandez, Susana; Armesto, Nuria; Ferrero, Miguel; Gotor, Vicente [Journal of Organic Chemistry, 2006, vol. 71, # 14, p. 5396 - 5399]
[4]Armesto, Nuria; Ferrero, Miguel; Fernandez, Susana; Gotor, Vicente [Journal of Organic Chemistry, 2002, vol. 67, # 14, p. 4978 - 4981]
[5]Location in patent: scheme or table Sanchez-Abella, Laura; Fernandez, Susana; Verstuyf, Annemieke; Verlinden, Lieve; Gotor, Vicente; Ferrero, Miguel [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 24, p. 10244 - 10250]
[6]Location in patent: scheme or table Payne, Richard J.; Bulloch, Esther M. M.; Toscano, Miguel M.; Jones, Michelle A.; Kerbarh, Olivier; Abell, Chris [Organic and Biomolecular Chemistry, 2009, vol. 7, # 11, p. 2421 - 2429]
[7]Current Patent Assignee: GLYCOMIMETICS, INC. - WO2010/126888, 2010, A1 Location in patent: Page/Page column 12; 34
[8]Sarandeses, Luis A.; Mascarenas, Jose L.; Castedo, Luis; Mourino, Antonio [Tetrahedron Letters, 1992, vol. 33, # 37, p. 5445 - 5448]
[9]Song; Jiang; Singh [Synlett, 2001, # 12, p. 1983 - 1985] Song, Chuanjun; Jiang, Shende; Singh, Gurdial [Tetrahedron Letters, 2001, vol. 42, # 51, p. 9069 - 9071]
[10]Song, Chuanjun; Jiang, Shende; Singh, Gurdial [Tetrahedron Asymmetry, 2003, vol. 14, # 18, p. 2833 - 2838]
[11]Huang, Jian; Chen, Fen-Er [Helvetica Chimica Acta, 2007, vol. 90, # 7, p. 1366 - 1372]
[12]Chahoua, Latifa; Baltas, Michel; Gorrichon, Liliane; Tisnes, Pierre; Zedde, Chantal [Journal of Organic Chemistry, 1992, vol. 57, # 21, p. 5798 - 5801]
[13]Current Patent Assignee: HAOYUAN CHEMEXPRESS - CN107501317, 2017, A Location in patent: Paragraph 0047; 0048; 0049; 0050; 0088; 0089
[14]Zhang, Yi; Liu, An; Ye, Zu Guang; Lin, Jia; Xu, Li Zhen; Yang, Shi Lin [Chemical and Pharmaceutical Bulletin, 2006, vol. 54, # 10, p. 1459 - 1461]
[15]Liu, An; Liu, Zhan Zhu; Zou, Zhong Mei; Chen, Shi Zhi; Xu, Li Zhen; Yang, Shi Lin [Tetrahedron, 2004, vol. 60, # 16, p. 3689 - 3694]
[16]Padala, Anil K.; Saikam, Varma; Ali, Asif; Ahmed, Qazi Naveed [Tetrahedron, 2015, vol. 71, # 50, p. 9388 - 9395]
[17]Sheng, Jianfei; Liu, Zhihong; Yan, Ming; Zhang, Xuejing; Wang, Dejian; Xu, Jun; Zhang, Ensheng; Zou, Yong [Organic and Biomolecular Chemistry, 2017, vol. 15, # 23, p. 4971 - 4977]
[18]Psotka, Miroslav; Martinková, Miroslava; Gonda, Jozef [Chemical Papers, 2017, vol. 71, # 4, p. 709 - 719]
[19]Du, Lin; Munteanu, Charissa; King, Jarrod B.; Frantz, Doug E.; Cichewicz, Robert H. [Journal of Natural Products, 2019, vol. 82, # 7, p. 1989 - 1999]
[20]Grewe et al. [Chemische Berichte, 1956, vol. 89, p. 898,901] Fischer; Dangschat [Helvetica Chimica Acta, 1934, vol. 17, p. 1200,1201][Helvetica Chimica Acta, 1935, vol. 18, p. 1206,1207]
[21]Brettle, Roger; Cross, Richard; Frederickson, Martyn; Haslam, Edwin; Davies, Gareth M. [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 3, p. 291 - 294]
[22]Brettle; Cross; Frederickson; Haslam; MacBeath; Davies [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 11, p. 1275 - 1278]
[23]Sanchez-Abella, Laura; Fernandez, Susana; Verstuyf, Annemieke; Verlinden, Lieve; Ferrero, Miguel; Gotor, Vicente [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 12, p. 4193 - 4202]
[24]Current Patent Assignee: GLYCOMIMETICS, INC. - US2009/253646, 2009, A1 Location in patent: Page/Page column 7
[25]Current Patent Assignee: GLYCOMIMETICS, INC. - US2007/54870, 2007, A1 Location in patent: Page/Page column 13
[26]Location in patent: experimental part Wu, Wei; Zou, Yong; Chen, Yu; Li, Jun; Lv, Zeliang; Wei, Wen; Huang, Tongkun; Liu, Xianke [Green Chemistry, 2012, vol. 14, # 2, p. 363 - 370]
[27]Current Patent Assignee: GLYCOMIMETICS, INC. - WO2012/61662, 2012, A1 Location in patent: Page/Page column 63
[28]Just, Jeremy; Deans, Bianca J.; Olivier, Wesley J.; Paull, Brett; Bissember, Alex C.; Smith, Jason A. [Organic Letters, 2015, vol. 17, # 10, p. 2428 - 2430]
[29]Wang, Dejian; Zhang, Ensheng; Xu, Tianlong; Sheng, Jianfei; Zou, Yong [Synlett, 2016, vol. 27, # 2, p. 287 - 293]
[30]Current Patent Assignee: LIAONING UNIVERSITY - CN109134480, 2019, A Location in patent: Paragraph 0049-0053
[31]Zhou, Shengfeng; Zhu, Runyu; Hu, Jingwen; Zhang, Lixiong; Lu, Qian; Yu, Xinhong [Organic Process Research and Development, 2019, vol. 23, # 9, p. 1887 - 1891]

3
[ 138-59-0 ]
[ 108-24-7 ]
[ 98167-08-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	In pyridine for 5h;
54%	With perchloric acid; acetic acid at 20 - 60℃;
34.8%	With pyridine at 0℃; Inert atmosphere;	1 Compound 43: (3R,4S,5R)-3,4,5-triacetoxycyclohex-1 -ene-1 -carboxylic acid Acetic anhydride (1 .61 ml_,17.2 mmol) was added dropwise to a stirred solution of shikimic acid (0.300 g,1 .72 mmol) in anhydrous pyridine (1 .38 mL,1 7.2 mmol) at 0°C under N atmosphere. The resulting stirred solution was left to come to room temperature and reaction was monitored to completion by LCMS. The solution was diluted with 20 mL of ethyl acetate and washed with 1 M HCI (20 mL) and saturated NaCI (20 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated by rotary evaporation. The crude residue was purified by flash chromatography (silica,10-90% acetonitrile in water) and fractions were concentrated by rotary evaporation to yield compound 43 (0.18 g,34.8% yield) as a white solid. -NMR (DMSO-de,400 MHz): d 12.90 (s,1 H),6.61 (dt,1 H), 5.60 (m, (0900) 1 H), 5.18 (dd,1 H), 5.12 (dt,1 H), 2.76 (m,1 H), 2.35 (m,1 H), 2.04 (s, 5H), 2.01 (s,3H). LC-MS: 299.1 (M- H)-

34.8%	With pyridine at 0 - 20℃; Inert atmosphere;	Compound 215: (3R,4S,5R)-3,4,5-triacetoxycyclohex-1-ene-1-carboxylic acid Acetic anhydride (1 .61 ml_, 17.2 mmol) was added dropwise to a stirred solution of shikimic acid (0.300 g, 1 .72 mmol) in anhydrous pyridine (1 .38 ml_, 17.2 mmol) at 0C under N2 atmosphere. The resulting stirred solution was left to come to room temperature and reaction was monitored to completion by LCMS. The solution was diluted with 20 ml_ of ethyl acetate and washed with 1 M HCI (20 ml_) and saturated NaCI (20 ml_). The organic layer was dried over magnesium sulfate, filtered, and concentrated by rotary evaporation. The crude residue was purified by flash chromatography (silica, 10-90% acetonitrile in water) and fractions were concentrated by rotary evaporation to yield compound 43 (0.18 g, 34.8% yield) as a white solid. 1H-NMR (DMSO-de, 400 MHz): d 12.90 (s, 1H), 6.61 (dt, 1H), 5.60 (m, 1H), 5.18 (dd, 1H), 5.12 (dt, 1H), 2.76 (m, 1H), 2.35 (m, 1H), 2.04 (S,5H), 2.01 (S,3H). LC-MS: 299.1 (M- H)-
	With pyridine

Reference： [1]Carbain, Benoit; Hitchcock, Peter B.; Streicher, Hansjörg [Tetrahedron Letters, 2010, vol. 51, # 20, p. 2717 - 2719]
[2]Srinivas, Ramishetti; Karmali, Priya P.; Pramanik, Dipankar; Garu, Arup; Mahidhar, Yenugonda Venkata; Majeti, Bharat K.; Ramakrishna, Sistla; Srinivas, Gunda; Chaudhuri, Arabinda [Journal of Medicinal Chemistry, 2010, vol. 53, # 3, p. 1387 - 1391]
[3]Current Patent Assignee: FLAGSHIP PIONEERING INC - WO2019/236775, 2019, A1 Location in patent: Page/Page column 67; 88
[4]Current Patent Assignee: FLAGSHIP PIONEERING INC - WO2019/236772, 2019, A1 Location in patent: Page/Page column 156
[5]Yamashita; Sato [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1930, vol. 50, p. 113,116; dtsch. Ref. S. 19][Chem.Abstr., 1930, p. 2739]
[6]Fischer; Dangschat [Helvetica Chimica Acta, 1935, vol. 18, p. 1206,1210]

4
[ 138-59-0 ]
[ 2922-42-1 ]

Yield	Reaction Conditions	Operation in experiment
60%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 65℃;
	With NAD(P)-independent quinate dehydrogenase EC 1.1.99.25; potassium hexacyanoferrate(III)
	With oxygen In water at 20℃; for 336h;

Reference： [1]McKittrick, Brian A.; Ganem, Bruce [Journal of Organic Chemistry, 1985, vol. 50, # 26, p. 5897 - 5898]
[2]Adachi, Osao; Yoshihara, Nozomi; Tanasupawat, Somboon; Toyama, Hirohide; Matsushita, Kazunobu [Bioscience, Biotechnology and Biochemistry, 2003, vol. 67, # 10, p. 2115 - 2123]
[3]Location in patent: experimental part Tonucci, Lucia; Nicastro, Marco; D'Alessandro, Nicola; Bressan, Mario; D'Ambrosio, Primiano; Morvillo, Antonino [Green Chemistry, 2009, vol. 11, # 6, p. 816 - 820]

5
[ 138-59-0 ]
(-)-shikimate 3-phosphate trisodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With ATP shikimate kinase, 1.) 6 h, 2.) 13 deg C_., overnight;
	Multi-step reaction with 11 steps 1: 95 percent / Amberlite IR 120 / 12 h / Heating 2: 96 percent / camphorsulfonic acid / 0.25 h / Ambient temperature 3: 100 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature 4: 94 percent / aq. HOAc / tetrahydrofuran / 6 h / 70 °C 5: 1.) dibutyltin oxide / 1.) benzene, reflux, 1 h, 2.) DMF, 30 min 6: 100 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 50 °C 7: 89 percent / 80percent aq. HOAc / 0.25 h 8: tetrazole / CH₂Cl₂ / 2 h / Ambient temperature 9: 0.304 g / m-CPBA / CH₂Cl₂ / 2 h / -40 °C 10: 80 percent / bromotrimethylsilane / CH₂Cl₂ / 1 h / 0 °C 11: 99 percent / 1 N NaOH / 3 h / 0 °C

Reference： [1]Castellino, Stephen; Leo, Gregory C.; Sammons, R. Douglas; Sikorski, James A. [Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5176 - 5181]
[2]Chahoua, Latifa; Baltas, Michel; Gorrichon, Liliane; Tisnes, Pierre; Zedde, Chantal [Journal of Organic Chemistry, 1992, vol. 57, # 21, p. 5798 - 5801]

6
[ 40983-58-2 ]
[ 138-59-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium hydroxide In tetrahydrofuran; water for 5.5h; Ambient temperature;
96%	With sodium hydroxide In tetrahydrofuran; water
96%	With sodium hydroxide; water In tetrahydrofuran for 1h; Ambient temperature;

86%	With hydrogenchloride; water at 60 - 70℃; for 12h;
80%	alkaline hydrolysis;
	Multi-step reaction with 5 steps 1: 90 percent / p-toluenesulfonic acid, Na₂CO₃ / CH₂Cl₂ / 5 °C 2: imidazole / dimethylformamide / 1.75 h 3: 1.) H₂O, AcOH; 2.) N,N-dimethylolpyridine / 1.) methanol, toluene, r.t., 1 h; 2) ether, 1 h 4: 80 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / 5 °C 5: 90 percent / aq.NaOH / methanol / 2.5 h / 5 - 25 °C
	Multi-step reaction with 8 steps 1: 90 percent / p-toluenesulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature; under nitrogen gas 2: imidazole / dimethylformamide / 1 h / 45 °C / under nitrogen gas 3: water / conc. HCl / methanol / 1 h / Ambient temperature 4: Jones reagent (CrO₃ in H₂SO₄) / acetone / 1 h / Ambient temperature; different ratios of reagent and different reaction times 5: NaBD₄ / ethanol / 5 °C 6: acetylation in the usual manner 7: 83 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / 5 °C 8: 1.) and 2.) NaOH / 1.) in methanol-water, 5 deg C, 0.5h; 2.) room temp., 2h
	Multi-step reaction with 7 steps 1: 90 percent / p-toluenesulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature; under nitrogen gas 2: imidazole / dimethylformamide / 1 h / 45 °C / under nitrogen gas 3: water / conc. HCl / methanol / 1 h / Ambient temperature 4: potassium acetate / 1.5 h / 70 °C 5: 1.) water / 1.) conc. HCl / 1.) methanol, room temp., 1h; 2.) re-acetylation 6: 83 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / 5 °C 7: 1.) and 2.) NaOH / 1.) in methanol-water, 5 deg C, 0.5h; 2.) room temp., 2h
	Multi-step reaction with 6 steps 1: 90 percent / p-toluenesulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature; under nitrogen gas 2: imidazole / dimethylformamide / 1 h / 45 °C / under nitrogen gas 3: water / conc. HCl / methanol / 1 h / Ambient temperature 4: acetylation in the usual manner 5: 83 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / 5 °C 6: 1.) and 2.) NaOH / 1.) in methanol-water, 5 deg C, 0.5h; 2.) room temp., 2h
	Multi-step reaction with 9 steps 1: 90 percent / p-toluenesulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature; under nitrogen gas 2: imidazole / dimethylformamide / 1 h / 45 °C / under nitrogen gas 3: water / conc. HCl / methanol / 1 h / Ambient temperature 4: pyridinium dichromate / dimethylformamide / 1 h / 45 °C / under nitrogen gas 5: NaBH₄ / ethanol / 0.25 h / 5 °C 6: potassium acetate / 1.5 h / 70 °C 7: 1.) water / 1.) conc. HCl / 1.) methanol, room temp., 1h; 2.) re-acetylation 8: 83 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / 5 °C 9: 1.) and 2.) NaOH / 1.) in methanol-water, 5 deg C, 0.5h; 2.) room temp., 2h
	Multi-step reaction with 9 steps 1: 90 percent / p-toluenesulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature; under nitrogen gas 2: imidazole / dimethylformamide / 1 h / 45 °C / under nitrogen gas 3: water / conc. HCl / methanol / 1 h / Ambient temperature 4: pyridinium dichromate / dimethylformamide / 1 h / 45 °C / under nitrogen gas 5: NaBH₄ / ethanol / 0.25 h / 5 °C 6: potassium acetate / 1.5 h / 70 °C 7: 1.) water / 1.) conc. HCl / 1.) methanol, room temp., 1h; 2.) re-acetylation 8: 83 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / 5 °C 9: 1.) and 2.) NaOH / 1.) in methanol-water, 5 deg C, 0.5h; 2.) room temp., 2h
	Multi-step reaction with 5 steps 1: 90 percent / p-toluenesulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature; under nitrogen gas 2: imidazole / dimethylformamide / 1 h / 45 °C / under nitrogen gas 3: 1.) water / 1.) conc. HCl / 1.) methanol, room temp., 1h; 2.) re-acetylation 4: 83 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / 5 °C 5: 1.) and 2.) NaOH / 1.) in methanol-water, 5 deg C, 0.5h; 2.) room temp., 2h

Reference： [1]Pawlak, John L.; Berchtold, Glenn A. [Journal of Organic Chemistry, 1987, vol. 52, # 9, p. 1765 - 1771]
[2]Kamikubo, Takashi; Ogasawara, Kunio [Chemistry Letters, 1996, # 11, p. 987 - 988]
[3]Hiroya, Kou; Ogasawara, Kunio [Chemical Communications, 1998, # 18, p. 2033 - 2034]
[4]Humphreys, Jane L.; Lowes, David J.; Wesson, Karen A.; Whitehead, Roger C. [Tetrahedron, 2006, vol. 62, # 21, p. 5099 - 5108]
[5]Fleet, George W. J.; Shing, Tony K. M. [Journal of the Chemical Society. Chemical communications, 1983, # 15, p. 849 - 850]
[6]Zamir, Lolita O.; Luthe, Corinne [Canadian Journal of Chemistry, 1984, vol. 62, p. 1169 - 1175]
[7]Luthe, Corinne; Zamir, Lolita O. [Tetrahedron Letters, 1983, vol. 24, # 41, p. 4409 - 4412]
[8]Luthe, Corinne; Zamir, Lolita O. [Tetrahedron Letters, 1983, vol. 24, # 41, p. 4409 - 4412]
[9]Luthe, Corinne; Zamir, Lolita O. [Tetrahedron Letters, 1983, vol. 24, # 41, p. 4409 - 4412]
[10]Luthe, Corinne; Zamir, Lolita O. [Tetrahedron Letters, 1983, vol. 24, # 41, p. 4409 - 4412]
[11]Luthe, Corinne; Zamir, Lolita O. [Tetrahedron Letters, 1983, vol. 24, # 41, p. 4409 - 4412]
[12]Luthe, Corinne; Zamir, Lolita O. [Tetrahedron Letters, 1983, vol. 24, # 41, p. 4409 - 4412]

7
[ 91758-39-3 ]
[ 138-59-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydroxide In methanol at 5 - 25℃; for 2.5h;
	With sodium hydroxide 1.) in methanol-water, 5 deg C, 0.5h; 2.) room temp., 2h; Multistep reaction;

Reference： [1]Zamir, Lolita O.; Luthe, Corinne [Canadian Journal of Chemistry, 1984, vol. 62, p. 1169 - 1175]
[2]Luthe, Corinne; Zamir, Lolita O. [Tetrahedron Letters, 1983, vol. 24, # 41, p. 4409 - 4412]

8
(3R,4S,5R)-3-[(tert-butyldimethylsilyl)oxy]-4,5-(2,3-dimethoxybutan-2,3-dioxy)cyclohex-1-ene-1-carboxylic acid [ No CAS ]
[ 138-59-0 ]

Yield	Reaction Conditions	Operation in experiment
53%	With trifluoroacetic acid In water

Reference： [1]Shinada, Tetsuro; Yoshida, Yasutaka; Ohfune, Yasufumi [Tetrahedron Letters, 1998, vol. 39, # 33, p. 6027 - 6028]

9
[ 138-59-0 ]
5-O-(p-coumaroyl)shikimic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	In water at 35℃; for 6h; dark; shikimate-p-hydroxycinnamoyl transferase;

Reference： [1]Ulbrich, Bernhard; Zenk, Meinhart H. [Phytochemistry, 1980, vol. 19, # 8, p. 1625 - 1629]

10
[ 138-59-0 ]
[ 67436-13-9 ]
[ 75932-02-4 ]
Fmoc-Gly-O-Wang ester resin [ No CAS ]
N^α,N^ε-Bis-[(3R,4S,5R)-3,4,5-trihydroxycyclohexanecarbonyl]-L-lysyl-[S-(tert-butylthio)]-L-cysteinyl-glycine [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 2967 - 2975

11
[ 138-59-0 ]
[ 431-03-8 ]
[ 149-73-5 ]
[ 245054-32-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sulfuric acid In methanol for 48h; Inert atmosphere; Reflux;
80%	With 10-camphorsufonic acid In methanol at 85℃;
70%	With CSA In methanol for 48h; Inert atmosphere; Reflux;

62%

With (1S)-10-camphorsulfonic acid In methanol for 72h; Reflux; Inert atmosphere;

Reference： [1]Blanco, Beatriz; Prado, Veronica; Lence, Emilio; Otero, Jose M.; Garcia-Doval, Carmela; Van Raaij, Mark J.; Llamas-Saiz, Antonio L.; Lamb, Heather; Hawkins, Alastair R.; Gonzalez-Bello, Concepcion [Journal of the American Chemical Society, 2013, vol. 135, # 33, p. 12366 - 12376]
[2]Armesto; Ferrero; Fernandez; Gotor [Tetrahedron Letters, 2000, vol. 41, # 45, p. 8759 - 8762]
[3]Location in patent: scheme or table Dinh, Tung N.; Chen, Anqi; Chai, Christina L.L. [Tetrahedron, 2011, vol. 67, # 19, p. 3363 - 3368]
[4]Carbain, Benoit; Hitchcock, Peter B.; Streicher, Hansjörg [Tetrahedron Letters, 2010, vol. 51, # 20, p. 2717 - 2719]

12
[ 138-59-0 ]
[ 171963-37-4 ]
[ 99-06-9 ]
[ 108-95-2 ]

Yield	Reaction Conditions	Operation in experiment
	In water at 250℃; for 0.5h;

Reference： [1]Gibson, James M.; Thomas, Phillip S.; Thomas, Joshua D.; Barker, Jessica L.; Chandran, Sunil S.; Harrup, Mason K.; Draths, Karen M.; Frost, John W. [Angewandte Chemie - International Edition, 2001, vol. 40, # 10, p. 1945 - 1948]

13
[ 138-59-0 ]
[ 99-06-9 ]
[ 108-95-2 ]
[ 99-96-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 51% 2: 18 % Chromat. 3: 1 % Chromat.	Stage #1: shikimic acid In water at 350℃; for 0.5h; Stage #2: With copper In water at 350℃;

Reference： [1]Gibson, James M.; Thomas, Phillip S.; Thomas, Joshua D.; Barker, Jessica L.; Chandran, Sunil S.; Harrup, Mason K.; Draths, Karen M.; Frost, John W. [Angewandte Chemie - International Edition, 2001, vol. 40, # 10, p. 1945 - 1948]

14
[ 138-59-0 ]
[ 99-06-9 ]
[ 99-96-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 57% 2: 9%	With sulfuric acid; acetic acid at 120℃; for 16h;
1: 13% 2: 40%	With hydrogenchloride for 14h; Heating;

Reference： [1]Gibson, James M.; Thomas, Phillip S.; Thomas, Joshua D.; Barker, Jessica L.; Chandran, Sunil S.; Harrup, Mason K.; Draths, Karen M.; Frost, John W. [Angewandte Chemie - International Edition, 2001, vol. 40, # 10, p. 1945 - 1948]
[2]Gibson, James M.; Thomas, Phillip S.; Thomas, Joshua D.; Barker, Jessica L.; Chandran, Sunil S.; Harrup, Mason K.; Draths, Karen M.; Frost, John W. [Angewandte Chemie - International Edition, 2001, vol. 40, # 10, p. 1945 - 1948]

15
[ 138-59-0 ]
C₃₃H₅₆N₈O₁₁S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	Stage #1: shikimic acid; H-Lys-Cys(StBu)-Arg(Pmc)-2,2,5,7,8-pentamethylchroma-6-sulfonyl peptidyl-resin With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.666667h; Stage #2: With chlorotriisopropylsilane; trifluoroacetic acid In water at 20℃; for 1h;

Reference： [1]Angyalosi, Gerhild; Grandjean, Cyrille; Lamirand, Melanie; Auriault, Claude; Gras-Masse, Helene; Melnyk, Oleg [Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 19, p. 2723 - 2727]

16
[ 138-59-0 ]
C₂₉H₄₇N₅O₁₁S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	Stage #1: shikimic acid; H-Lys-Cys(StBu)-Gly-2,2,5,7,8-pentamethylchroma-6-sulfonyl peptidyl-resin With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.666667h; Stage #2: With chlorotriisopropylsilane; trifluoroacetic acid In water at 20℃; for 1h;

Reference： [1]Angyalosi, Gerhild; Grandjean, Cyrille; Lamirand, Melanie; Auriault, Claude; Gras-Masse, Helene; Melnyk, Oleg [Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 19, p. 2723 - 2727]

17
[ 109-65-9 ]
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35661-39-3 ]
(1R,2S,3S,4S,5R)-2-(4-Butylsulfanyl-2,3-dihydroxy-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

18
[ 109-65-9 ]
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-14-5 ]
(S)-3-[(1R,2S,3S,4S,5R)-2-(4-Butylsulfanyl-2,3-dihydroxy-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-succinamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

19
[ 109-65-9 ]
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-18-9 ]
(S)-4-[(1R,2S,3S,4S,5R)-2-(4-Butylsulfanyl-2,3-dihydroxy-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-4-carbamoyl-butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

20
[ 446-48-0 ]
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35661-39-3 ]
(1R,2S,3S,4S,5R)-2-[4-(2-Fluoro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

21
[ 446-48-0 ]
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-14-5 ]
(S)-3-({(1R,2S,3S,4S,5R)-2-[4-(2-Fluoro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-succinamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

22
[ 446-48-0 ]
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-18-9 ]
(S)-4-Carbamoyl-4-({(1R,2S,3S,4S,5R)-2-[4-(2-fluoro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

23
[ 6892-68-8 ]
[ 111-83-1 ]
[ 138-59-0 ]
[ 35661-39-3 ]
(1R,2S,3S,4S,5R)-2-(2,3-Dihydroxy-4-octylsulfanyl-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

24
[ 6892-68-8 ]
[ 111-83-1 ]
[ 138-59-0 ]
[ 71989-14-5 ]
(S)-3-[(1R,2S,3S,4S,5R)-2-(2,3-Dihydroxy-4-octylsulfanyl-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-succinamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

25
[ 6892-68-8 ]
[ 111-83-1 ]
[ 138-59-0 ]
[ 71989-18-9 ]
(S)-4-Carbamoyl-4-[(1R,2S,3S,4S,5R)-2-(2,3-dihydroxy-4-octylsulfanyl-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

26
[ 6892-68-8 ]
[ 5292-43-3 ]
[ 138-59-0 ]
[ 35661-39-3 ]
{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-ethylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanyl}-acetic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

27
[ 6892-68-8 ]
[ 5292-43-3 ]
[ 138-59-0 ]
[ 71989-14-5 ]
(S)-3-[(1R,2S,3S,4S,5R)-2-(4-tert-Butoxycarbonylmethylsulfanyl-2,3-dihydroxy-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-succinamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

28
[ 6892-68-8 ]
[ 5292-43-3 ]
[ 138-59-0 ]
[ 71989-18-9 ]
(S)-4-[(1R,2S,3S,4S,5R)-2-(4-tert-Butoxycarbonylmethylsulfanyl-2,3-dihydroxy-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-4-carbamoyl-butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

29
[ 6892-68-8 ]
[ 24356-14-7 ]
[ 138-59-0 ]
[ 35661-39-3 ]
2-{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-ethylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanyl}-hexanoic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

30
[ 6892-68-8 ]
[ 24356-14-7 ]
[ 138-59-0 ]
[ 71989-14-5 ]
2-{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-2-carboxy-ethylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanyl}-hexanoic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

31
[ 6892-68-8 ]
[ 24356-14-7 ]
[ 138-59-0 ]
[ 71989-18-9 ]
2-{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-3-carboxy-propylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanyl}-hexanoic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

32
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35661-39-3 ]
[ 14704-31-5 ]
(1R,2S,3S,4S,5R)-2-[4-(Biphenyl-3-ylmethylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide [ No CAS ]

Reference： [1]Organic letters,2003,vol. 5,p. 1407 - 1410

33
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35661-39-3 ]
[ 35132-16-2 ]
{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-ethylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanyl}-phenyl-acetic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

34
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35661-39-3 ]
[ 108052-76-2 ]
4-{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-ethylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanylmethyl}-benzoic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

35
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35661-39-3 ]
[ 126062-63-3 ]
3-{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-ethylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanylmethyl}-benzoic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

36
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35661-39-3 ]
[ 42877-95-2 ]
2-{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-ethylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanyl}-3-methyl-butyric acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

37
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35661-39-3 ]
[ 536711-05-4 ]
4-{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-ethylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanylmethyl}-phthalic acid di-tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

38
[ 6892-68-8 ]
[ 138-59-0 ]
[ 14704-31-5 ]
[ 71989-14-5 ]
(S)-3-({(1R,2S,3S,4S,5R)-2-[4-(Biphenyl-3-ylmethylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-succinamic acid [ No CAS ]

Reference： [1]Organic letters,2003,vol. 5,p. 1407 - 1410

39
[ 6892-68-8 ]
[ 138-59-0 ]
[ 14704-31-5 ]
[ 71989-18-9 ]
(S)-4-({(1R,2S,3S,4S,5R)-2-[4-(Biphenyl-3-ylmethylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-4-carbamoyl-butyric acid [ No CAS ]

Reference： [1]Organic letters,2003,vol. 5,p. 1407 - 1410

40
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35132-16-2 ]
[ 71989-14-5 ]
(S)-3-({(1R,2S,3S,4S,5R)-2-[4-(tert-Butoxycarbonyl-phenyl-methylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-succinamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

41
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35132-16-2 ]
[ 71989-18-9 ]
(S)-4-({(1R,2S,3S,4S,5R)-2-[4-(tert-Butoxycarbonyl-phenyl-methylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-4-carbamoyl-butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

42
[ 6892-68-8 ]
[ 138-59-0 ]
[ 108052-76-2 ]
[ 71989-14-5 ]
4-{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-2-carboxy-ethylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanylmethyl}-benzoic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

43
[ 6892-68-8 ]
[ 138-59-0 ]
[ 108052-76-2 ]
[ 71989-18-9 ]
4-{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-3-carboxy-propylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanylmethyl}-benzoic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

44
[ 6892-68-8 ]
[ 138-59-0 ]
[ 126062-63-3 ]
[ 71989-14-5 ]
3-{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-2-carboxy-ethylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanylmethyl}-benzoic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

45
[ 6892-68-8 ]
[ 138-59-0 ]
[ 126062-63-3 ]
[ 71989-18-9 ]
3-{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-3-carboxy-propylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanylmethyl}-benzoic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

46
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-14-5 ]
[ 42877-95-2 ]
2-{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-2-carboxy-ethylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanyl}-3-methyl-butyric acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

47
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-14-5 ]
[ 536711-05-4 ]
4-{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-2-carboxy-ethylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanylmethyl}-phthalic acid di-tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

48
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-18-9 ]
[ 42877-95-2 ]
2-{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-3-carboxy-propylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanyl}-3-methyl-butyric acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

49
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-18-9 ]
[ 536711-05-4 ]
4-{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-3-carboxy-propylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanylmethyl}-phthalic acid di-tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

50
[ 27565-41-9 ]
[ 138-59-0 ]
[ 35661-39-3 ]
[ 14704-31-5 ]
(1R,2S,3S,4S,5R)-2-[4-(Biphenyl-3-ylmethylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide [ No CAS ]

Reference： [1]Organic letters,2003,vol. 5,p. 1407 - 1410

51
[ 27565-41-9 ]
[ 138-59-0 ]
[ 35661-39-3 ]
[ 35132-16-2 ]
{4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-ethylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanyl}-phenyl-acetic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

52
[ 27565-41-9 ]
[ 138-59-0 ]
[ 14704-31-5 ]
[ 71989-14-5 ]
(S)-3-({(1R,2S,3S,4S,5R)-2-[4-(Biphenyl-3-ylmethylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-succinamic acid [ No CAS ]

Reference： [1]Organic letters,2003,vol. 5,p. 1407 - 1410

53
[ 27565-41-9 ]
[ 138-59-0 ]
[ 14704-31-5 ]
[ 71989-18-9 ]
(S)-4-({(1R,2S,3S,4S,5R)-2-[4-(Biphenyl-3-ylmethylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-4-carbamoyl-butyric acid [ No CAS ]

Reference： [1]Organic letters,2003,vol. 5,p. 1407 - 1410

54
[ 27565-41-9 ]
[ 138-59-0 ]
[ 35132-16-2 ]
[ 71989-14-5 ]
(S)-3-({(1R,2S,3S,4S,5R)-2-[4-(tert-Butoxycarbonyl-phenyl-methylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-succinamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

55
[ 27565-41-9 ]
[ 138-59-0 ]
[ 35132-16-2 ]
[ 71989-18-9 ]
(S)-4-({(1R,2S,3S,4S,5R)-2-[4-(tert-Butoxycarbonyl-phenyl-methylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-4-carbamoyl-butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

56
[ 35661-60-0 ]
[ 138-59-0 ]
[ 39088-65-8 ]
4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-3-methyl-butylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanylmethyl]-benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

57
[ 138-59-0 ]
[ 35661-39-3 ]
[ 39088-65-8 ]
4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-ethylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanylmethyl]-benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

58
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35661-39-3 ]
[ 100-39-0 ]
(1R,2S,3S,4S,5R)-2-(4-Benzylsulfanyl-2,3-dihydroxy-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

59
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-14-5 ]
[ 100-39-0 ]
(S)-3-[(1R,2S,3S,4S,5R)-2-(4-Benzylsulfanyl-2,3-dihydroxy-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-succinamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

60
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-18-9 ]
[ 100-39-0 ]
(S)-4-[(1R,2S,3S,4S,5R)-2-(4-Benzylsulfanyl-2,3-dihydroxy-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-4-carbamoyl-butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

61
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35661-39-3 ]
[ 2550-36-9 ]
(1R,2S,3S,4S,5R)-2-(4-Cyclohexylmethylsulfanyl-2,3-dihydroxy-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

62
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-14-5 ]
[ 2550-36-9 ]
(S)-3-[(1R,2S,3S,4S,5R)-2-(4-Cyclohexylmethylsulfanyl-2,3-dihydroxy-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-succinamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

63
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-18-9 ]
[ 2550-36-9 ]
(S)-4-Carbamoyl-4-[(1R,2S,3S,4S,5R)-2-(4-cyclohexylmethylsulfanyl-2,3-dihydroxy-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

64
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35661-39-3 ]
[ 766-80-3 ]
(1R,2S,3S,4S,5R)-2-[4-(3-Chloro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

65
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-14-5 ]
[ 766-80-3 ]
(S)-3-({(1R,2S,3S,4S,5R)-2-[4-(3-Chloro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-succinamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

66
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-18-9 ]
[ 766-80-3 ]
(S)-4-Carbamoyl-4-({(1R,2S,3S,4S,5R)-2-[4-(3-chloro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

67
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35661-39-3 ]
[ 459-46-1 ]
(1R,2S,3S,4S,5R)-2-[4-(4-Fluoro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

68
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-14-5 ]
[ 459-46-1 ]
(S)-3-({(1R,2S,3S,4S,5R)-2-[4-(4-Fluoro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-succinamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

69
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-18-9 ]
[ 459-46-1 ]
(S)-4-Carbamoyl-4-({(1R,2S,3S,4S,5R)-2-[4-(4-fluoro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

70
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35661-39-3 ]
[ 20443-98-5 ]
(1R,2S,3S,4S,5R)-2-[4-(2,6-Dichloro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

71
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-14-5 ]
[ 20443-98-5 ]
(S)-3-({(1R,2S,3S,4S,5R)-2-[4-(2,6-Dichloro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-succinamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

72
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-18-9 ]
[ 20443-98-5 ]
(S)-4-Carbamoyl-4-({(1R,2S,3S,4S,5R)-2-[4-(2,6-dichloro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

73
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35661-39-3 ]
[ 3958-60-9 ]
(1R,2S,3S,4S,5R)-2-[2,3-Dihydroxy-4-(2-nitro-benzylsulfanyl)-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

74
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-14-5 ]
[ 3958-60-9 ]
(S)-3-({(1R,2S,3S,4S,5R)-2-[2,3-Dihydroxy-4-(2-nitro-benzylsulfanyl)-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-succinamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

75
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-18-9 ]
[ 3958-60-9 ]
(S)-4-Carbamoyl-4-({(1R,2S,3S,4S,5R)-2-[2,3-dihydroxy-4-(2-nitro-benzylsulfanyl)-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

76
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35661-39-3 ]
[ 1765-40-8 ]
(1R,2S,3S,4S,5R)-2-(2,3-Dihydroxy-4-pentafluorophenylmethylsulfanyl-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

77
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-14-5 ]
[ 1765-40-8 ]
(S)-3-[(1R,2S,3S,4S,5R)-2-(2,3-Dihydroxy-4-pentafluorophenylmethylsulfanyl-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-succinamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

78
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-18-9 ]
[ 1765-40-8 ]
(S)-4-Carbamoyl-4-[(1R,2S,3S,4S,5R)-2-(2,3-dihydroxy-4-pentafluorophenylmethylsulfanyl-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

79
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35661-39-3 ]
[ 100-11-8 ]
(1R,2S,3S,4S,5R)-2-[2,3-Dihydroxy-4-(4-nitro-benzylsulfanyl)-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

80
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-14-5 ]
[ 100-11-8 ]
(S)-3-({(1R,2S,3S,4S,5R)-2-[2,3-Dihydroxy-4-(4-nitro-benzylsulfanyl)-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-succinamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

81
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-18-9 ]
[ 100-11-8 ]
(S)-4-Carbamoyl-4-({(1R,2S,3S,4S,5R)-2-[2,3-dihydroxy-4-(4-nitro-benzylsulfanyl)-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

82
[ 6892-68-8 ]
[ 138-59-0 ]
[ 35661-39-3 ]
[ 112-89-0 ]
(1R,2S,3S,4S,5R)-2-(2,3-Dihydroxy-4-octadecylsulfanyl-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

83
[ 6892-68-8 ]
[ 138-59-0 ]
[ 71989-14-5 ]
[ 112-89-0 ]
(S)-3-[(1R,2S,3S,4S,5R)-2-(2,3-Dihydroxy-4-octadecylsulfanyl-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-succinamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Schuster, Michael C; Mann, David A; Buchholz, Tonia J; Johnson, Kathryn M; Thomas, William D; Kiessling, Laura L [Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410]

84
[ 2280-44-6 ]
[ 138-59-0 ]
[ 178948-66-8 ]

Yield	Reaction Conditions	Operation in experiment
5%	Stage #1: D-Glucose With Bacillus pumilus ATCC 21143; oxygen In various solvent(s) at 30℃; for 96h; Microbiological reaction; Stage #2: Escherichia coli SP_1.1/pJG_6.181B With oxygen In various solvent(s) at 37℃; Microbiological reaction;

Reference： [1]Guo, Jiantao; Frost [Organic Letters, 2004, vol. 6, # 10, p. 1585 - 1588]

85
[ 138-59-0 ]
[ 4265-07-0 ]
[ 617-12-9 ]
[ 85506-20-3 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 2043 - 2051

86
[ 138-59-0 ]
[ 101906-39-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 96 percent / (+) cation resin / 15 h / Heating 2: 95 percent / 1H-imidazole; DMAP / dimethylformamide / 12 h / 0 - 25 °C
	Multi-step reaction with 2 steps 1: 100 percent / HCl / 6 h / 60 °C 2: 75 percent / Et₃N; DMAP / dimethylformamide / 1 h / 20 °C
	Multi-step reaction with 2 steps 1: 98 percent / HCl / 4 h / 60 °C 2: 82 percent / Et₃N, DMAP / dimethylformamide / 6 h / 0 °C

	Multi-step reaction with 2 steps 1: methanol; diethyl ether / -20 - -15 °C 2: 78 percent / Et₃N, 4-(dimethylamino)pyridine / dimethylformamide / 4 h / 0 °C
	Multi-step reaction with 2 steps 1: acetyl chloride / 0 - 20 °C / Inert atmosphere 2: tetrabutylammomium bromide; dmap; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

Reference： [1]Huang, Jian; Chen, Fen-Er [Helvetica Chimica Acta, 2007, vol. 90, # 7, p. 1366 - 1372]
[2]Sanchez-Abella, Laura; Fernandez, Susana; Armesto, Nuria; Ferrero, Miguel; Gotor, Vicente [Journal of Organic Chemistry, 2006, vol. 71, # 14, p. 5396 - 5399]
[3]Sarandeses, Luis A.; Mascarenas, Jose L.; Castedo, Luis; Mourino, Antonio [Tetrahedron Letters, 1992, vol. 33, # 37, p. 5445 - 5448]
[4]Meier; Tamm [Helvetica Chimica Acta, 1991, vol. 74, # 4, p. 807 - 818]
[5]Current Patent Assignee: HAOYUAN CHEMEXPRESS - CN107501317, 2017, A

87
[ 138-59-0 ]
[ 245054-32-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 93 percent / SOCl₂ / 10 °C 2: 90 percent / (+/-)-CSA / methanol / 48 h / 90 °C
	Multi-step reaction with 2 steps 1: 93 percent / SOCl₂ / 0 - 20 °C 2: 87 percent / (+/-)-camphorsulfonic acid / methanol / 48 h / 90 °C
	Multi-step reaction with 3 steps 1: 93 percent / SOCl₂ / 0 - 20 °C 2: 12 percent / (+/-)-camphorsulfonic acid / methanol / 48 h / 90 °C 3: 92 percent / (+/-)-camphorsulfonic acid / methanol / 18 h / Heating

Multi-step reaction with 2 steps 1: hydrogenchloride / 5 h / 60 °C 2: dmap / methanol

Reference： [1]Zhang, Yi; Liu, An; Ye, Zu Guang; Lin, Jia; Xu, Li Zhen; Yang, Shi Lin [Chemical and Pharmaceutical Bulletin, 2006, vol. 54, # 10, p. 1459 - 1461]
[2]Liu, An; Liu, Zhan Zhu; Zou, Zhong Mei; Chen, Shi Zhi; Xu, Li Zhen; Yang, Shi Lin [Tetrahedron, 2004, vol. 60, # 16, p. 3689 - 3694]
[3]Liu, An; Liu, Zhan Zhu; Zou, Zhong Mei; Chen, Shi Zhi; Xu, Li Zhen; Yang, Shi Lin [Tetrahedron, 2004, vol. 60, # 16, p. 3689 - 3694]
[4]Psotka, Miroslav; Martinková, Miroslava; Gonda, Jozef [Chemical Papers, 2017, vol. 71, # 4, p. 709 - 719]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	138-59-0	MDL No. :	MFCD00066278
Formula :	C₇H₁₀O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JXOHGGNKMLTUBP-HSUXUTPPSA-N
M.W :	174.15	Pubchem ID :	8742
Synonyms :	NSC 59257;Shikimate;(–)-Shikimic Acid, L-Shikimic Acid, Shikimic acid;L-Shikimic Acid;(–)-Shikimic Acid

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.57
Num. rotatable bonds :	1
Num. H-bond acceptors :	5.0
Num. H-bond donors :	4.0
Molar Refractivity :	38.43
TPSA :	97.99 Å²

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.58 cm/s

Log Po/w (iLOGP) :	0.02
Log Po/w (XLOGP3) :	-1.72
Log Po/w (WLOGP) :	-1.52
Log Po/w (MLOGP) :	-1.43
Log Po/w (SILICOS-IT) :	-1.36
Consensus Log Po/w :	-1.2

[ CAS No. 138-59-0 ] {[proInfo.proName]}

Quality Control of [ 138-59-0 ]

Related Doc. of [ 138-59-0 ]

Product Details of [ 138-59-0 ]

Calculated chemistry of [ 138-59-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 138-59-0 ]

Application In Synthesis of [ 138-59-0 ]

[ 138-59-0 ] Synthesis Path-Downstream 1~87

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Log S (ESOL) :	0.23
Solubility :	296.0 mg/ml ; 1.7 mol/l
Class :	Highly soluble
Log S (Ali) :	0.18
Solubility :	261.0 mg/ml ; 1.5 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	1.75
Solubility :	9750.0 mg/ml ; 56.0 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.77

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

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling