Name: 477-47-4|(5R,5aS,8aR,9R)-9-Hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one|98%
Brand: Ambeed
SKU: A359248
Price: 19.0 USD
Availability: InStock
Rating: 97 (22 reviews)

1
[ 908094-01-9 ]
[ 112066-16-7 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; diethyl ether; acetone

Reference： [1]Nadkarni et al. [Journal of the American Chemical Society, 1953, vol. 75, p. 1308,1311]

2
[ 77-78-1 ]
[ 112066-16-7 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide

Reference： [1]Nadkarni et al. [Journal of the American Chemical Society, 1953, vol. 75, p. 1308,1311]

3
[ 77-78-1 ]
[ 40505-27-9 ]
[ 477-47-4 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 1308,1311

4
[ 4375-06-8 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; acetone

Reference： [1]Hartwell; Schrecker [Journal of the American Chemical Society, 1951, vol. 73, p. 2909,2916]

5
[ 108-30-5 ]
[ 477-47-4 ]
[ 47789-93-5 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine

Reference： [1]Schrecker et al. [Journal of the American Chemical Society, 1955, vol. 77, p. 6565,6566]

6
[ 16837-38-0 ]
[ 477-47-4 ]
(5aS)-9c-nicotinoyloxy-5c-(3,4,5-trimethoxy-phenyl)-(5ar,8ac)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine

Reference： [1]Schrecker et al. [Journal of the American Chemical Society, 1955, vol. 77, p. 6565,6566]

7
[ 108-24-7 ]
[ 477-47-4 ]
[ 38491-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine
	With sodium acetate
	With pyridine at 60℃; for 1h;	1 Example 1 (5R,5aR,8aS.9R)-8-oxo-9-(3.4.5-trimethoxyphenyl)-5,5a.6.8.8a.9- 6Χ3νΓθυΓθΓ3'.4':6.7η3ρΗΜοΓ2.3-Γ1.3οχο[-5-νΙ acetate Example 1 (5R,5aR,8aS.9R)-8-oxo-9-(3.4.5-trimethoxyphenyl)-5,5a.6.8.8a.9- 6Χ3νΓθυΓθΓ3'.4':6.7η3ρΗΜοΓ2.3-Γ1.3οχο[-5-νΙ acetate PPP (21 mg, 0.05 mmol) was mixed with pyridine (0.12 mL) and acetic anhydride (0.047 mL). The mixture was heated to 60 °C and stirred for 1 hour. Then methanol (2 mL) was added and precipitate was formed. The mixture was concentrated under reduced pressure and the residue was suspended in ethyl acetate and washed with hydrochloric acid (1 M aq), water and NaHC03 (sat). The organic phase was dried over Na2S04, filtered and evaporated to give the product (21 mg) in 92% yield. The organic phase was dried over Na2S04, filtered and evaporated to give the product (21 mg) in 92% yield and 90% purity according to LCMS (ACE 3 C8, 50 x 3.0 mm, 10% to 97% acetonitrile in 3 min in 0.1% TFA in water, 1 mL/min), MS ESI+ m/z 397, rt 2.112

Reference： [1]Gensler; Wang [Journal of the American Chemical Society, 1954, vol. 76, p. 5890] Spaeth; Wessely; Kornfeld [Chemische Berichte, 1932, vol. 65, p. 1536,1549] Gensler et al. [Journal of the American Chemical Society, 1960, vol. 82, p. 1714,1724]
[2]Borsche; Niemann [Justus Liebigs Annalen der Chemie, 1932, vol. 494, p. 126,142][Justus Liebigs Annalen der Chemie, 1932, vol. 499, p. 59,67] Spaeth; Wessely; Kornfeld [Chemische Berichte, 1932, vol. 65, p. 1536,1549]
[3]Current Patent Assignee: AXELAR AB - WO2013/132262, 2013, A1 Location in patent: Page/Page column 17

8
[ 98-88-4 ]
[ 477-47-4 ]
[ 78215-98-2 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine

Reference： [1]Drake; Price [Journal of the American Chemical Society, 1951, vol. 73, p. 201,203] Hartwell; Schrecker [Journal of the American Chemical Society, 1951, vol. 73, p. 2909,2916]

9
[ 541-88-8 ]
[ 477-47-4 ]
O-chloroacetyl-picropodophyllin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine

Reference： [1]Schrecker et al. [Journal of the American Chemical Society, 1954, vol. 76, p. 1182]

10
[ 477-47-4 ]
[ 6258-41-9 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium at 240℃;

Reference： [1]Spaeth; Wessely; Kornfeld [Chemische Berichte, 1932, vol. 65, p. 1536,1549]

11
[ 477-47-4 ]
[ 344585-17-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With Amberlyst In acetic anhydride for 0.5h; Heating;
	With sulfuric acid; acetic anhydride
	With phosphorus trichloride; benzene

	With hydrogenchloride; acetic acid
	With chloroform; phosphorus pentachloride

Reference： [1]Buchardt; Jensen; Hansen; Nielsen; Andersen; Chinoin [Journal of Pharmaceutical Sciences, 1986, vol. 75, # 11, p. 1076 - 1080]
[2]Robertson; Waters [Journal of the Chemical Society, 1933, p. 83,86] Schrecker; Hartwell [Journal of the American Chemical Society, 1952, vol. 74, p. 5676,5682] Borsche; Niemann [Justus Liebigs Annalen der Chemie, 1932, vol. 494, p. 126,142][Justus Liebigs Annalen der Chemie, 1932, vol. 499, p. 59,67] Spaeth; Wessely; Kornfeld [Chemische Berichte, 1932, vol. 65, p. 1536,1549]
[3]Hartwell; Schrecker [Journal of the American Chemical Society, 1951, vol. 73, p. 2909,2916]
[4]Schrecker; Hartwell [Journal of the American Chemical Society, 1954, vol. 76, p. 752]
[5]Borsche; Niemann [Justus Liebigs Annalen der Chemie, 1932, vol. 494, p. 126,142][Justus Liebigs Annalen der Chemie, 1932, vol. 499, p. 59,67]

12
[ 477-47-4 ]
[ 477-48-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With pyridine; chromium(VI) oxide In dichloromethane at 20℃; for 3h;
	With manganese(IV) oxide; chloroform
	In dimethyl sulfoxide for 72h; Forsythia intermedia; Yield given;

	With chromium(VI) oxide In pyridine for 3h; Ambient temperature; Yield given;
	With manganese(IV) oxide
162 mg	With chromium(VI) oxide In pyridine Ambient temperature;
200 mg	With dipyridinium dichromate In dichloromethane for 3h; Ambient temperature;

Reference： [1]Wang, Yi; Shao, Yonghua; Wang, Yangyang; Fan, Lingling; Yu, Xiang; Zhi, Xiaoyan; Yang, Chun; Qu, Huan; Yao, Xiaojun; Xu, Hui [Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 34, p. 8435 - 8443]
[2]Gensler; Johnson [Journal of the American Chemical Society, 1955, vol. 77, p. 3674]
[3]Broomhead, A. Jane; Dewick, Paul M. [Phytochemistry, 1991, vol. 30, # 5, p. 1511 - 1517]
[4]Feliciano, A. San; Lopez, J. L.; Medarde, M.; Corral, J. M. Miduel del; Pascual-Teresa, B. de; Puebla, P. [Tetrahedron, 1988, vol. 44, # 23, p. 7255 - 7260]
[5]Dewick, Paul M.; Jackson, David E. [Phytochemistry, 1981, vol. 20, # 9, p. 2277 - 2280]
[6]Lopez-Perez, Jose L.; Olmo, Ester del; Pascual-Teresa, Beatriz de; Merino, Marta; Martin, Sara; Feliciano, Arturo San [Tetrahedron, 1995, vol. 51, # 22, p. 6343 - 6348]
[7]Del Corral; Gordaliza; Lopez; Del Olmo; Castro; Lopez [Helvetica Chimica Acta, 1995, vol. 78, # 7, p. 1793 - 1796]

13
[ 477-47-4 ]
[ 245321-94-2 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; sulfuric acid

Reference： [1]Schrecker; Hartwell [Journal of the American Chemical Society, 1954, vol. 76, p. 752]

14
[ 518-28-5 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium hydroxide In methanol for 0.5h; Ambient temperature;
90%	With potassium hydroxide In methanol for 1h; Ambient temperature;
78%	With sodium acetate In ethanol; water for 12h; Heating;

73%	With sodium acetate In ethanol; water for 15h; Reflux;
72%	With sodium acetate In ethanol; water at 80℃; for 18h;
69%	With sodium acetate In ethanol; water for 15.5h; Reflux;	Synthesis of picropodophyllotoxin (1c) A mixture of1a(2.072 g, 5.0 mmol), absolute ethanol (31 mL), and 10% aq. CH3CO2Na (21 mL) was refluxed. When the reaction was complete for 15.5 h checked by TLC analysis, the mixture was cooled to 0oC and filtered to give the solid, which was recrystallized from absolute ethanol to afford1c(1.419 g, 69% yield). CAS: 1370530-62-3. White solid, m.p. 222-223oC.[α]20D= +5 (c3.2 mg/mL, CHCl3).1H NMR (500 MHz, DMSO-d6)δ: 7.06 (s, 1H, H-5), 6.60 (s, 2H, H-2′, 6′), 6.00 (s, 1H, H-8), 5.91-5.95 (m, 3H, H-4 and OCH2O), 4.51 (d,J= 9.0 Hz, 1H, H-1), 4.34-4.41 (m, 2H, H-11), 3.92 (d,J= 7.5 Hz, 1H, H-2), 3.74 (s, 6H, 3′, 5′-OCH3), 3.69 (s, 3H, 4′-OCH3), 3.40-3.44 (m, 1H, H-3).13C NMR (125 MHz, DMSO-d6)δ: 177.9, 152.8, 145.7, 145.6, 138.3, 136.1, 134.7, 131.4, 107.2, 106.3, 104.4, 100.6, 69.2, 67.2, 59.9, 55.8, 43.6, 43.2, 42.7. MS (ESI-TRAP),m/z(%): 432 ([M+NH4]+, 100).
	With ethanol; sodium acetate
	With methanol; palladium
	With piperidine; methanol
	With sodium hydroxide In chloroform for 12h;
394 mg	With potassium hydroxide In methanol for 4h; Ambient temperature;
	With borate buffer In 1,4-dioxane; water at 37℃; pH = 10; ionic strength 0.2;
	Multi-step reaction with 2 steps 1: 68 percent / PCC / CH₂Cl₂ / 6 h / Ambient temperature; other reagent 2: 98 percent / NaBH₄ / 0 °C
	With sodium acetate In ethanol; water for 12h; Heating / reflux;	Picropodophyllin and deoxypicropodophyllin are then prepared from purified podophyllotoxin and deoxypodophyllotoxin, respectively, using essentially identical procedures. Picropodophyllin was dissolved in 70% aqueous ethanol. To the solution was added sodium acetate and the mixture was then refluxed and stirred for 12 h. The mixture was cooled and filtered. The product (precipitate) was washed with ethyl acetate, and then purified by recrystallization from absolute ethanol essentially as described by 0 Buchardt et al . (J Pharmaceut Sci 1986; 75 : 1076-1080) or purified by chromatography on silica gel, mobile phase: hexane-ethyl acetate mixtures, and/or octadecylsilane-bonded silica, mobile phase: aqueous methanol
	With sodium acetate In ethanol; water

Reference： [1]Del Corral; Gordaliza; Lopez; Del Olmo; Castro; Lopez [Helvetica Chimica Acta, 1995, vol. 78, # 7, p. 1793 - 1796]
[2]Castro, M. A.; Gordaliza, M.; Corral, J. M. Miguel del; Feliciano, A. San [Organic Preparations and Procedures International, 1994, vol. 26, # 5, p. 539 - 548]
[3]Buchardt; Jensen; Hansen; Nielsen; Andersen; Chinoin [Journal of Pharmaceutical Sciences, 1986, vol. 75, # 11, p. 1076 - 1080]
[4]Wang, Yi; Shao, Yonghua; Wang, Yangyang; Fan, Lingling; Yu, Xiang; Zhi, Xiaoyan; Yang, Chun; Qu, Huan; Yao, Xiaojun; Xu, Hui [Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 34, p. 8435 - 8443]
[5]Wang, Rong; Zhi, Xiaoyan; Li, Jie; Xu, Hui [Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 30, p. 6668 - 6674]
[6]Che, Zhiping; Yu, Xiang; Fan, Lingling; Xu, Hui [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 20, p. 5592 - 5598]
[7]Drake; Price [Journal of the American Chemical Society, 1951, vol. 73, p. 201,203] Borsche; Niemann [Justus Liebigs Annalen der Chemie, 1932, vol. 494, p. 126,142][Justus Liebigs Annalen der Chemie, 1932, vol. 499, p. 59,67]
[8]Borsche; Niemann [Justus Liebigs Annalen der Chemie, 1932, vol. 494, p. 126,142][Justus Liebigs Annalen der Chemie, 1932, vol. 499, p. 59,67]
[9]Robertson; Waters [Journal of the Chemical Society, 1933, p. 83,86]
[10]Thurston, Lee S.; Irie, Hiroshi; Tani, Shohei; Han, Fu-Sheng; Liu, Zong-Chao; et al. [Journal of Medicinal Chemistry, 1986, vol. 29, # 8, p. 1547 - 1550]
[11]Lopez-Perez, Jose L.; Olmo, Ester del; Pascual-Teresa, Beatriz de; Merino, Marta; Martin, Sara; Feliciano, Arturo San [Tetrahedron, 1995, vol. 51, # 22, p. 6343 - 6348]
[12]Aso; Hayashi; Yoshioka; Takeda; Kita; Nishimura; Arata [Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 2, p. 422 - 424]
[13]Kamal, Ahmed; Damayanthi [Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 657 - 662]
[14]Current Patent Assignee: AXELAR AB - WO2007/97707, 2007, A1 Location in patent: Page/Page column 14; 19
[15]Location in patent: scheme or table Xu, Hui; He, Xiao-Qiang [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 15, p. 4503 - 4506]

15
[ 477-48-5 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With lithium tri(t-butoxy)aluminum hydride In tetrahydrofuran for 3.5h; Ambient temperature;
80.4%	Stage #1: (5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione With methanol; sodium tetrahydroborate at 0 - 20℃; Stage #2: With ammonium acetate In water	6 Example 6Synthesis of Picropodophyllin, i.e. (11 S 5R)-16-hydroxy-10-(3A5-trimethoxyphenyl)- 4.6.13- trioxatetracvclor7.7.0.0A(3, 7).0A{ 11 , 15)1hexadeca- 1.3i7).8-trien-12-one(1 1 R,15S)-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo-[7.7.0.0A{3,7}.0A{1 1 ,15}]hexadeca- 1 .3(7),8-triene-10,14-dione obtained in analogy with Example 5 (40 g, 97.09 mmol) was suspended in methanol (700 mL) and the resulting mixture cooled to 0 °C. Sodium borohydride (7.39 g, 194.18 mmol) was added in portions over 2 h and the resulting mixture stirred at r.t. overnight. Aqueous ammonium acetate (1 M, 200 mL) was added and the formed precipitate collected by filtration. The filter-cake was washed with 50 vol-% methanol in water (4 x 50 mL) and dried to constant weight under vacuum overnight to give a solid. The mother liquid was ectracted with dichloromethane (3 x 500 mL); the organic solution was washed with brine and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was combined with the dried solid and recrystallized from dichloromethane and hexane to afford a white solid (32.3 g). Yield: 80.4% LCMS ACE 3 C8, 50 x 3.0 mm, 10%-97% acetonitrile in 0.1 % TFA in water, 1 mL/min showed 97% chromatographic purity, MS [M+NH4]+ 432 (100), [M-OH]+ 3971H-NMR (400 MHz, DMSO-d6): δ [ppm] = 2.50-2.58 (m, 1 H, overlapping with solvent residue signal), 3.42 (dd, 1 H), 3.70 (s, 3H), 3.76 (s, 6H), 3.92 (d, 1 H), 3.98 (bs, 1 H), 4.36 (d, 1 H), 4.41 (dd, 1 H), 4.51 (dd, 1 H), 5.42 (app. d, 2H), 6.03 (s, 1 H), 6.50 (s, 2H), 7.08 (s, 1 H) Specific rotation: [a]28D (c = 0.27 in chloroform) +13.0°

Reference： [1]Andrews, Robert C.; Teague, Simon J.; Meyers, A. I. [Journal of the American Chemical Society, 1988, vol. 110, # 23, p. 7854 - 7858]
[2]Current Patent Assignee: AXELAR AB - WO2012/30284, 2012, A1 Location in patent: Page/Page column 22

16
[ 64-17-5 ]
[ 477-47-4 ]
[ 78215-99-3 ]
[ 245321-94-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 34% 2: 52%	With Amberlyst for 2h; Heating;

Reference： [1]Buchardt; Jensen; Hansen; Nielsen; Andersen; Chinoin [Journal of Pharmaceutical Sciences, 1986, vol. 75, # 11, p. 1076 - 1080]

17
[ 69739-34-0 ]
[ 477-47-4 ]
[ 108448-52-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With 2,6-dimethylpyridine In dichloromethane at 0℃; for 4h;

Reference： [1]Andrews, Robert C.; Teague, Simon J.; Meyers, A. I. [Journal of the American Chemical Society, 1988, vol. 110, # 23, p. 7854 - 7858]

18
[ 477-47-4 ]
4-chloro-4-deoxypicropodophyllotoxin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride In chloroform for 0.166667h; Ambient temperature;

Reference： [1]Hansen; Jensen; Willumsen; Norskov-Lauritsen; Ebbesen; Nielsen; Buchardt [Acta Chemica Scandinavica, 1993, vol. 47, # 12, p. 1190 - 1200]

19
[ 477-47-4 ]
[ 3811-15-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With lithium aluminium tetrahydride In diethyl ether Ambient temperature;
	With lithium aluminium tetrahydride In diethyl ether at 20℃; for 3h;

Reference： [1]Castro, M. A.; Gordaliza, M.; Corral, J. M. Miguel del; Feliciano, A. San [Organic Preparations and Procedures International, 1994, vol. 26, # 5, p. 539 - 548]
[2]Gordaliza, Marina; Miguel Del Corral, Jose M.; Angeles Castro; Garcia-Garcia, Pablo A.; San Feliciano, Arturo [Il Farmaco, 2001, vol. 56, # 4, p. 297 - 304]

20
podophyllotoxone [ No CAS ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium tetrahydroborate at 0℃;

Reference： [1]Kamal, Ahmed; Damayanthi [Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 657 - 662]

21
[ 75-08-1 ]
[ 261158-29-6 ]
(5R,5aS,8aR,9R)-9-Ethylsulfanyl-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one [ No CAS ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 65% 2: 8%	With magnesium bromide In diethyl ether; benzene at 0 - 20℃; for 11h;

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; acetic acid Erhitzen des Reaktionsprodukts mit wss. Aceton und Calciumcarbonat;

23
[ 110-87-2 ]
[ 477-47-4 ]
[ 13311-04-1 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid for 1h;	Briefly, picropodophyllin was first converted to tetrahydropyranyl- picropodophyllin. Picropodophyllin was dissolved in the reagent dihydropyran plus some small crystals of p-toluenesulfonic acid monohydrate and the mixture was stirred for Ih. A 3% aqueous bicarbonate solution was then added, the volatiles removed in vacuo, and the residue (containing tetrahydropyranylpicropodo- phyllin) was then extracted with diethyl ether and washed.The recovered tetrahydropyranylpicropodophyllin was then reduced to tetrahydropyranylpicropodophyllol . Tetrahydropyranylpicropodo- phyllin was dissolved in dry diethyl ether and lithium aluminum hydride was added. After 3.5 h of of stirring at room temperature, the mixture was cooled to O0C and then carefully treated with water. The produced tetrahydropyranylpicropodophyllol was then extracted by ethyl acetate and washed with water and dried. The recovered tetrahydropyranylpicropodophyllol was then converted to tetrahydropyranylanhydropicropodophyllol by dissolving the former in pyridine and then adding p-toluenesulfonyl chloride in pyridine. The mixture was allowed to react for 4.5 h without contact with air and then some extra of p-toluenesulfonyl chloride was added and the reaction was allowed to proceed for another 4.5 h. The product tetrahydropyranylanhydropicropodophyllol was then extracted with ethyl acetate from the water phase and dried. Tetrahydro- pyranylanhydropicropodophyllol was hydrolyzed to anhydropicro- podophyllol by dissolving the former in ethanol acidified with concentrated HCl and allowing the mixture to stand 1 h in room temperature. After neutralization with aqueous sodium bicarbonate, anhydropicropodophyllol was extracted with ethyl acetate and dried

Reference： [1]Current Patent Assignee: AXELAR AB - WO2007/97707, 2007, A1 Location in patent: Page/Page column 14; 15; 19

24
[ 18162-48-6 ]
[ 477-47-4 ]
[ 108448-52-8 ]

Yield	Reaction Conditions	Operation in experiment
	With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	An alternative method for the synthesis of anhydropicropodophyllol was also tested, and this method gave higher yields of the compound than the method described above. Briefly, the tert- butyldimethylsilyl ether of picropodophyllin was first prepared by adding tert-butyldimethylsilyl (t-BDMS) chloride under N2 to a mixture of picropodophyllin and imidazole in dimethylformamide. The yellow solution was stirred overnight at room temperature and poured into water. The derivative was purified prior to reduction of the lactone group with lithium aluminum hydride in tetrahydrofuran. The latter mixture was then stirred at room temperature for 3 hours yielding the t-BDMS derivative of picropodophyllol (having two free hydroxyl groups) . To a solution of this compound in dichloromethane was added triphenylphosphine and diethyl azodicarboxylate and the mixture was then stirred at room temperature for 3 hours. The solvent was evaporated and the crude t-BDMS ether of anhydropicropodophyllol was then purified.Underivatized anhydropicropodophyllol was obtained by adding tetrabutyl ammonium fluoride to a solution of the derivative in tetrahydrofuran. The mixture was then stirred at room temperature over night. After purification, free and pure anhydropicropodo- phyllol was obtained as a white solid

Reference： [1]Current Patent Assignee: AXELAR AB - WO2007/97707, 2007, A1 Location in patent: Page/Page column 15; 16; 19

25
[ 477-47-4 ]
[ 78391-86-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: LiAlH₄ / diethyl ether / 3 h / 20 °C 2: aq. HCl / CHCl₃ / 1 h / Heating
	Multi-step reaction with 2 steps 1: 80 percent / LAH / diethyl ether / Ambient temperature 2: 88 percent / HClaq_. / CHCl₃ / 1 h / Heating

Reference： [1]Gordaliza, Marina; Miguel Del Corral, Jose M.; Angeles Castro; Garcia-Garcia, Pablo A.; San Feliciano, Arturo [Il Farmaco, 2001, vol. 56, # 4, p. 297 - 304]
[2]Castro, M. A.; Gordaliza, M.; Corral, J. M. Miguel del; Feliciano, A. San [Organic Preparations and Procedures International, 1994, vol. 26, # 5, p. 539 - 548]

26
[ 477-47-4 ]
C₂₂H₂₂O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: LiAlH₄ / diethyl ether / 3 h / 20 °C 2: aq. HCl / CHCl₃ / 1 h / Heating 3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -55 - 0 °C

Reference： [1]Gordaliza, Marina; Miguel Del Corral, Jose M.; Angeles Castro; Garcia-Garcia, Pablo A.; San Feliciano, Arturo [Il Farmaco, 2001, vol. 56, # 4, p. 297 - 304]

27
[ 74879-22-4 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 18 steps 1.1: 61 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 2.1: 83 percent / NaBH₄ / ethanol / 20 °C 3.1: 90 percent / acetic acid / 2 h / 80 °C 4.1: 99 percent / H₂ / 10percent Pd/C / ethyl acetate / 6 h / 2482.38 Torr 5.1: 82 percent / LiAlH₄ / diethyl ether / 24 h / Heating 6.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 7.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 8.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 9.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 10.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 11.1: 90 percent / NaOMe / methanol / 20 °C 12.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 13.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 14.1: CDI / tetrahydrofuran / 3 h / 20 °C 14.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 15.1: CDI / tetrahydrofuran / 3 h / 20 °C 15.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 16.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 17.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 17.2: 62 percent / benzene; CHCl₃ / Heating 18.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C
	Multi-step reaction with 17 steps 1.1: 61 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 2.1: 83 percent / NaBH₄ / ethanol / 20 °C 3.1: 52 percent / acetic acid / 2 h / 80 °C 4.1: 82 percent / LiAlH₄ / diethyl ether / 24 h / Heating 5.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 6.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 7.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 8.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 9.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 10.1: 90 percent / NaOMe / methanol / 20 °C 11.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 12.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 13.1: CDI / tetrahydrofuran / 3 h / 20 °C 13.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 14.1: CDI / tetrahydrofuran / 3 h / 20 °C 14.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 15.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 16.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 16.2: 62 percent / benzene; CHCl₃ / Heating 17.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C
	Multi-step reaction with 17 steps 1.1: 61 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 2.1: 83 percent / NaBH₄ / ethanol / 20 °C 3.1: 29 percent / acetic acid / 2 h / 80 °C 4.1: 82 percent / LiAlH₄ / diethyl ether / 24 h / Heating 5.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 6.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 7.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 8.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 9.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 10.1: 90 percent / NaOMe / methanol / 20 °C 11.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 12.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 13.1: CDI / tetrahydrofuran / 3 h / 20 °C 13.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 14.1: CDI / tetrahydrofuran / 3 h / 20 °C 14.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 15.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 16.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 16.2: 62 percent / benzene; CHCl₃ / Heating 17.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

	Multi-step reaction with 17 steps 1.1: 82 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / 0 - 20 °C 2.1: 90 percent / acetic acid / 2 h / 80 °C 3.1: 99 percent / H₂ / 10percent Pd/C / ethyl acetate / 6 h / 2482.38 Torr 4.1: 82 percent / LiAlH₄ / diethyl ether / 24 h / Heating 5.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 6.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 7.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 8.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 9.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 10.1: 90 percent / NaOMe / methanol / 20 °C 11.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 12.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 13.1: CDI / tetrahydrofuran / 3 h / 20 °C 13.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 14.1: CDI / tetrahydrofuran / 3 h / 20 °C 14.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 15.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 16.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 16.2: 62 percent / benzene; CHCl₃ / Heating 17.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C
	Multi-step reaction with 16 steps 1.1: 82 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / 0 - 20 °C 2.1: 52 percent / acetic acid / 2 h / 80 °C 3.1: 82 percent / LiAlH₄ / diethyl ether / 24 h / Heating 4.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 5.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 6.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 7.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 8.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 9.1: 90 percent / NaOMe / methanol / 20 °C 10.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 11.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 12.1: CDI / tetrahydrofuran / 3 h / 20 °C 12.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 13.1: CDI / tetrahydrofuran / 3 h / 20 °C 13.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 14.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 15.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 15.2: 62 percent / benzene; CHCl₃ / Heating 16.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C
	Multi-step reaction with 16 steps 1.1: 82 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / 0 - 20 °C 2.1: 29 percent / acetic acid / 2 h / 80 °C 3.1: 82 percent / LiAlH₄ / diethyl ether / 24 h / Heating 4.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 5.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 6.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 7.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 8.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 9.1: 90 percent / NaOMe / methanol / 20 °C 10.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 11.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 12.1: CDI / tetrahydrofuran / 3 h / 20 °C 12.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 13.1: CDI / tetrahydrofuran / 3 h / 20 °C 13.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 14.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 15.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 15.2: 62 percent / benzene; CHCl₃ / Heating 16.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]
[2]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]
[3]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]
[4]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]
[5]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]
[6]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

28
[ 87850-43-9 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 17 steps 1.1: 83 percent / NaBH₄ / ethanol / 20 °C 2.1: 90 percent / acetic acid / 2 h / 80 °C 3.1: 99 percent / H₂ / 10percent Pd/C / ethyl acetate / 6 h / 2482.38 Torr 4.1: 82 percent / LiAlH₄ / diethyl ether / 24 h / Heating 5.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 6.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 7.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 8.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 9.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 10.1: 90 percent / NaOMe / methanol / 20 °C 11.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 12.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 13.1: CDI / tetrahydrofuran / 3 h / 20 °C 13.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 14.1: CDI / tetrahydrofuran / 3 h / 20 °C 14.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 15.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 16.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 16.2: 62 percent / benzene; CHCl₃ / Heating 17.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C
	Multi-step reaction with 16 steps 1.1: 83 percent / NaBH₄ / ethanol / 20 °C 2.1: 52 percent / acetic acid / 2 h / 80 °C 3.1: 82 percent / LiAlH₄ / diethyl ether / 24 h / Heating 4.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 5.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 6.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 7.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 8.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 9.1: 90 percent / NaOMe / methanol / 20 °C 10.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 11.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 12.1: CDI / tetrahydrofuran / 3 h / 20 °C 12.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 13.1: CDI / tetrahydrofuran / 3 h / 20 °C 13.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 14.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 15.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 15.2: 62 percent / benzene; CHCl₃ / Heating 16.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C
	Multi-step reaction with 16 steps 1.1: 83 percent / NaBH₄ / ethanol / 20 °C 2.1: 29 percent / acetic acid / 2 h / 80 °C 3.1: 82 percent / LiAlH₄ / diethyl ether / 24 h / Heating 4.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 5.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 6.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 7.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 8.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 9.1: 90 percent / NaOMe / methanol / 20 °C 10.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 11.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 12.1: CDI / tetrahydrofuran / 3 h / 20 °C 12.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 13.1: CDI / tetrahydrofuran / 3 h / 20 °C 13.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 14.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 15.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 15.2: 62 percent / benzene; CHCl₃ / Heating 16.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]
[2]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]
[3]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

29
[ 162285-50-9 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 16 steps 1.1: 90 percent / acetic acid / 2 h / 80 °C 2.1: 99 percent / H₂ / 10percent Pd/C / ethyl acetate / 6 h / 2482.38 Torr 3.1: 82 percent / LiAlH₄ / diethyl ether / 24 h / Heating 4.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 5.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 6.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 7.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 8.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 9.1: 90 percent / NaOMe / methanol / 20 °C 10.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 11.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 12.1: CDI / tetrahydrofuran / 3 h / 20 °C 12.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 13.1: CDI / tetrahydrofuran / 3 h / 20 °C 13.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 14.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 15.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 15.2: 62 percent / benzene; CHCl₃ / Heating 16.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C
	Multi-step reaction with 15 steps 1.1: 52 percent / acetic acid / 2 h / 80 °C 2.1: 82 percent / LiAlH₄ / diethyl ether / 24 h / Heating 3.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 4.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 5.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 6.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 7.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 8.1: 90 percent / NaOMe / methanol / 20 °C 9.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 10.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 11.1: CDI / tetrahydrofuran / 3 h / 20 °C 11.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 12.1: CDI / tetrahydrofuran / 3 h / 20 °C 12.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 13.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 14.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 14.2: 62 percent / benzene; CHCl₃ / Heating 15.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C
	Multi-step reaction with 15 steps 1.1: 29 percent / acetic acid / 2 h / 80 °C 2.1: 82 percent / LiAlH₄ / diethyl ether / 24 h / Heating 3.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 4.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 5.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 6.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 7.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 8.1: 90 percent / NaOMe / methanol / 20 °C 9.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 10.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 11.1: CDI / tetrahydrofuran / 3 h / 20 °C 11.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 12.1: CDI / tetrahydrofuran / 3 h / 20 °C 12.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 13.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 14.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 14.2: 62 percent / benzene; CHCl₃ / Heating 15.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]
[2]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]
[3]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

30
[ 179680-51-4 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 13 steps 1.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 2.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 3.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 4.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 5.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 6.1: 90 percent / NaOMe / methanol / 20 °C 7.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 8.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 9.1: CDI / tetrahydrofuran / 3 h / 20 °C 9.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 10.1: CDI / tetrahydrofuran / 3 h / 20 °C 10.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 11.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 12.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 12.2: 62 percent / benzene; CHCl₃ / Heating 13.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

31
[ 179680-50-3 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 14 steps 1.1: 82 percent / LiAlH₄ / diethyl ether / 24 h / Heating 2.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 3.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 4.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 5.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 6.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 7.1: 90 percent / NaOMe / methanol / 20 °C 8.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 9.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 10.1: CDI / tetrahydrofuran / 3 h / 20 °C 10.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 11.1: CDI / tetrahydrofuran / 3 h / 20 °C 11.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 12.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 13.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 13.2: 62 percent / benzene; CHCl₃ / Heating 14.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

32
[ 179680-49-0 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 15 steps 1.1: 99 percent / H₂ / 10percent Pd/C / ethyl acetate / 6 h / 2482.38 Torr 2.1: 82 percent / LiAlH₄ / diethyl ether / 24 h / Heating 3.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 4.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 5.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 6.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 7.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 8.1: 90 percent / NaOMe / methanol / 20 °C 9.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 10.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 11.1: CDI / tetrahydrofuran / 3 h / 20 °C 11.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 12.1: CDI / tetrahydrofuran / 3 h / 20 °C 12.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 13.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 14.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 14.2: 62 percent / benzene; CHCl₃ / Heating 15.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

33
[ 179680-52-5 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 12 steps 1.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 2.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 3.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 4.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 5.1: 90 percent / NaOMe / methanol / 20 °C 6.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 7.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 8.1: CDI / tetrahydrofuran / 3 h / 20 °C 8.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 9.1: CDI / tetrahydrofuran / 3 h / 20 °C 9.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 10.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 11.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 11.2: 62 percent / benzene; CHCl₃ / Heating 12.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

34
[ 179680-55-8 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 2.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 3.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 4.1: 90 percent / NaOMe / methanol / 20 °C 5.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 6.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 7.1: CDI / tetrahydrofuran / 3 h / 20 °C 7.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 8.1: CDI / tetrahydrofuran / 3 h / 20 °C 8.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 9.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 10.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 10.2: 62 percent / benzene; CHCl₃ / Heating 11.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

35
[ 184348-24-1 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 2.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 3.1: CDI / tetrahydrofuran / 3 h / 20 °C 3.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 4.1: CDI / tetrahydrofuran / 3 h / 20 °C 4.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 5.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 6.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 6.2: 62 percent / benzene; CHCl₃ / Heating 7.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

36
[ 184348-25-2 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: 90 percent / NaOMe / methanol / 20 °C 2.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 3.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 4.1: CDI / tetrahydrofuran / 3 h / 20 °C 4.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 5.1: CDI / tetrahydrofuran / 3 h / 20 °C 5.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 6.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 7.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 7.2: 62 percent / benzene; CHCl₃ / Heating 8.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

37
[ 184348-23-0 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 2.1: 90 percent / NaOMe / methanol / 20 °C 3.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 4.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 5.1: CDI / tetrahydrofuran / 3 h / 20 °C 5.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 6.1: CDI / tetrahydrofuran / 3 h / 20 °C 6.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 7.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 8.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 8.2: 62 percent / benzene; CHCl₃ / Heating 9.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

38
[ 184348-22-9 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: 100 percent / K₂CO₃ / methanol / 1.5 h / 20 °C 2.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -40 °C 3.1: 90 percent / NaOMe / methanol / 20 °C 4.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C 5.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 6.1: CDI / tetrahydrofuran / 3 h / 20 °C 6.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 7.1: CDI / tetrahydrofuran / 3 h / 20 °C 7.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 8.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 9.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 9.2: 62 percent / benzene; CHCl₃ / Heating 10.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

39
[ 184348-26-3 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 95 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C 2.1: CDI / tetrahydrofuran / 3 h / 20 °C 2.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 3.1: CDI / tetrahydrofuran / 3 h / 20 °C 3.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 4.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 5.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 5.2: 62 percent / benzene; CHCl₃ / Heating 6.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

40
[ 222979-17-1 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: CDI / tetrahydrofuran / 3 h / 20 °C 1.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 2.1: CDI / tetrahydrofuran / 3 h / 20 °C 2.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 3.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 4.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 4.2: 62 percent / benzene; CHCl₃ / Heating 5.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

41
[ 184348-27-4 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 2.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 2.2: 62 percent / benzene; CHCl₃ / Heating 3.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

42
[ 1025879-31-5 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: CDI / tetrahydrofuran / 3 h / 20 °C 1.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 2.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 3.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 3.2: 62 percent / benzene; CHCl₃ / Heating 4.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

43
[ 261158-28-5 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 1.2: 62 percent / benzene; CHCl₃ / Heating 2.1: 65 percent / MgBr₂*OEt₂ / benzene; diethyl ether / 11 h / 0 - 20 °C

Reference： [1]Berkowitz, David B.; Choi, Sungjo; Maeng, Jun-Ho [Journal of Organic Chemistry, 2000, vol. 65, # 3, p. 847 - 860]

44
[ 477-47-4 ]
[ 120090-82-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 200 mg / PDC / CH₂Cl₂ / 3 h / Ambient temperature 2: 1 percent KOH / methanol
	Multi-step reaction with 2 steps 1: CrO₃ / pyridine / 3 h / Ambient temperature 2: t-BuOK, H₂O / 2-methyl-propan-2-ol / 0.17 h / Ambient temperature
	Multi-step reaction with 2 steps 1: CrO₃ / pyridine / 3 h / Ambient temperature 2: 10percent KOH / methanol / 30 h / Ambient temperature

Reference： [1]Del Corral; Gordaliza; Lopez; Del Olmo; Castro; Lopez [Helvetica Chimica Acta, 1995, vol. 78, # 7, p. 1793 - 1796]
[2]Feliciano, A. San; Lopez, J. L.; Medarde, M.; Corral, J. M. Miduel del; Pascual-Teresa, B. de; Puebla, P. [Tetrahedron, 1988, vol. 44, # 23, p. 7255 - 7260]
[3]Feliciano, A. San; Lopez, J. L.; Medarde, M.; Corral, J. M. Miduel del; Pascual-Teresa, B. de; Puebla, P. [Tetrahedron, 1988, vol. 44, # 23, p. 7255 - 7260]

45
[ 477-47-4 ]
[ 155325-16-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaN₃, TFA / CHCl₃ / 1 h 2: 63 percent / H₂ / 5percent Pd/C / ethanol / 4 h / 40 °C

Reference： [1]Hansen; Jensen; Willumsen; Norskov-Lauritsen; Ebbesen; Nielsen; Buchardt [Acta Chemica Scandinavica, 1993, vol. 47, # 12, p. 1190 - 1200]

46
[ 477-47-4 ]
[ 155325-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: SOCl₂ / CHCl₃ / 0.17 h / Ambient temperature 2: NaN₃ / dimethylformamide / Ambient temperature 3: 61 percent / H₂ / 5percent Pd/C / ethanol / 4 h / 40 °C
	Multi-step reaction with 2 steps 1: NaN₃, TFA / CHCl₃ / 1 h 2: 61 percent / H₂ / 5percent Pd/C / ethanol / 4 h / 40 °C

Reference： [1]Hansen; Jensen; Willumsen; Norskov-Lauritsen; Ebbesen; Nielsen; Buchardt [Acta Chemica Scandinavica, 1993, vol. 47, # 12, p. 1190 - 1200]
[2]Hansen; Jensen; Willumsen; Norskov-Lauritsen; Ebbesen; Nielsen; Buchardt [Acta Chemica Scandinavica, 1993, vol. 47, # 12, p. 1190 - 1200]

47
[ 477-47-4 ]
[ 155325-20-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂ / CHCl₃ / 0.17 h / Ambient temperature 2: NaN₃ / dimethylformamide / Ambient temperature

Reference： [1]Hansen; Jensen; Willumsen; Norskov-Lauritsen; Ebbesen; Nielsen; Buchardt [Acta Chemica Scandinavica, 1993, vol. 47, # 12, p. 1190 - 1200]

48
[ 477-47-4 ]
4β-acetamido-4-deoxypicropodophyllotoxin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: NaN₃, TFA / CHCl₃ / 1 h 2: 63 percent / H₂ / 5percent Pd/C / ethanol / 4 h / 40 °C 3: 88 percent / pyridine / 1 h / 0 °C

Reference： [1]Hansen; Jensen; Willumsen; Norskov-Lauritsen; Ebbesen; Nielsen; Buchardt [Acta Chemica Scandinavica, 1993, vol. 47, # 12, p. 1190 - 1200]

49
[ 477-47-4 ]
4α-acetamido-4-deoxypicropodophyllotoxin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: SOCl₂ / CHCl₃ / 0.17 h / Ambient temperature 2: NaN₃ / dimethylformamide / Ambient temperature 3: 61 percent / H₂ / 5percent Pd/C / ethanol / 4 h / 40 °C 4: 88 percent / pyridine / 1 h / 0 °C
	Multi-step reaction with 3 steps 1: NaN₃, TFA / CHCl₃ / 1 h 2: 61 percent / H₂ / 5percent Pd/C / ethanol / 4 h / 40 °C 3: 88 percent / pyridine / 1 h / 0 °C

Reference： [1]Hansen; Jensen; Willumsen; Norskov-Lauritsen; Ebbesen; Nielsen; Buchardt [Acta Chemica Scandinavica, 1993, vol. 47, # 12, p. 1190 - 1200]
[2]Hansen; Jensen; Willumsen; Norskov-Lauritsen; Ebbesen; Nielsen; Buchardt [Acta Chemica Scandinavica, 1993, vol. 47, # 12, p. 1190 - 1200]

50
[ 117179-02-9 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 74 percent / xylene / 36 h / 210 °C 2: 94 percent / lithium tri-tert-butoxyaluminum hydride / tetrahydrofuran / 3.5 h / Ambient temperature

Reference： [1]Andrews, Robert C.; Teague, Simon J.; Meyers, A. I. [Journal of the American Chemical Society, 1988, vol. 110, # 23, p. 7854 - 7858]

51
[ 117097-47-9 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 100 percent / N-bromosuccinimide, DMSO / tetrahydrofuran / 6 h / 0 °C 2: 79 percent / azobis(isobutyronitrile), tri-n-butyltin hydride / toluene / 4 h / 120 °C 3: 87 percent / pyridinium dichromate, 3A molecular sieves / CH₂Cl₂ / 4 h / Ambient temperature 4: 1.) 5 N sodium hydroxide, 2.) p-toluenesulfonic acid / 1.) THF, H₂O, 26 h, r. t., 2.) aq. EtOH, 60 - 65 deg C, 24 h 5: 74 percent / xylene / 36 h / 210 °C 6: 94 percent / lithium tri-tert-butoxyaluminum hydride / tetrahydrofuran / 3.5 h / Ambient temperature

Reference： [1]Andrews, Robert C.; Teague, Simon J.; Meyers, A. I. [Journal of the American Chemical Society, 1988, vol. 110, # 23, p. 7854 - 7858]

52
[ 117097-50-4 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) 5 N sodium hydroxide, 2.) p-toluenesulfonic acid / 1.) THF, H₂O, 26 h, r. t., 2.) aq. EtOH, 60 - 65 deg C, 24 h 2: 74 percent / xylene / 36 h / 210 °C 3: 94 percent / lithium tri-tert-butoxyaluminum hydride / tetrahydrofuran / 3.5 h / Ambient temperature

Reference： [1]Andrews, Robert C.; Teague, Simon J.; Meyers, A. I. [Journal of the American Chemical Society, 1988, vol. 110, # 23, p. 7854 - 7858]

53
(-)-(1R,2S,3S,4R)-1-(3,4,5-trimethoxyphenyl)-2-(methoxycarbonyl)-3-<<(tert-butyldimethylsilyl)oxy>methyl>-4-hydroxy-6,7-(methylenedioxy)-1,2,3,4-tetrahydronaphtalene [ No CAS ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 87 percent / pyridinium dichromate, 3A molecular sieves / CH₂Cl₂ / 4 h / Ambient temperature 2: 1.) 5 N sodium hydroxide, 2.) p-toluenesulfonic acid / 1.) THF, H₂O, 26 h, r. t., 2.) aq. EtOH, 60 - 65 deg C, 24 h 3: 74 percent / xylene / 36 h / 210 °C 4: 94 percent / lithium tri-tert-butoxyaluminum hydride / tetrahydrofuran / 3.5 h / Ambient temperature

Reference： [1]Andrews, Robert C.; Teague, Simon J.; Meyers, A. I. [Journal of the American Chemical Society, 1988, vol. 110, # 23, p. 7854 - 7858]

54
(5R,6R,7R,8R)-7-Bromo-7-(tert-butyl-dimethyl-silanyloxymethyl)-8-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester [ No CAS ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 79 percent / azobis(isobutyronitrile), tri-n-butyltin hydride / toluene / 4 h / 120 °C 2: 87 percent / pyridinium dichromate, 3A molecular sieves / CH₂Cl₂ / 4 h / Ambient temperature 3: 1.) 5 N sodium hydroxide, 2.) p-toluenesulfonic acid / 1.) THF, H₂O, 26 h, r. t., 2.) aq. EtOH, 60 - 65 deg C, 24 h 4: 74 percent / xylene / 36 h / 210 °C 5: 94 percent / lithium tri-tert-butoxyaluminum hydride / tetrahydrofuran / 3.5 h / Ambient temperature

Reference： [1]Andrews, Robert C.; Teague, Simon J.; Meyers, A. I. [Journal of the American Chemical Society, 1988, vol. 110, # 23, p. 7854 - 7858]

55
[ 477-52-1 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 96 percent / 5 N aq. sodium hydroxide / methanol; H₂O / 8 h / 60 °C 2: 2.) 4-(dimethylamino)pyridine, trimethylamine / 1.) ether, THF, 10 min, 2.) CH₂Cl₂, 0 deg C, 30 min, 3.) CH₂Cl₂, 10 min, r. t. 3: 100 percent / N-bromosuccinimide, DMSO / tetrahydrofuran / 6 h / 0 °C 4: 79 percent / azobis(isobutyronitrile), tri-n-butyltin hydride / toluene / 4 h / 120 °C 5: 87 percent / pyridinium dichromate, 3A molecular sieves / CH₂Cl₂ / 4 h / Ambient temperature 6: 1.) 5 N sodium hydroxide, 2.) p-toluenesulfonic acid / 1.) THF, H₂O, 26 h, r. t., 2.) aq. EtOH, 60 - 65 deg C, 24 h 7: 74 percent / xylene / 36 h / 210 °C 8: 94 percent / lithium tri-tert-butoxyaluminum hydride / tetrahydrofuran / 3.5 h / Ambient temperature

Reference： [1]Andrews, Robert C.; Teague, Simon J.; Meyers, A. I. [Journal of the American Chemical Society, 1988, vol. 110, # 23, p. 7854 - 7858]

56
α-apopicropodophyllic acid [ No CAS ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 2.) 4-(dimethylamino)pyridine, trimethylamine / 1.) ether, THF, 10 min, 2.) CH₂Cl₂, 0 deg C, 30 min, 3.) CH₂Cl₂, 10 min, r. t. 2: 100 percent / N-bromosuccinimide, DMSO / tetrahydrofuran / 6 h / 0 °C 3: 79 percent / azobis(isobutyronitrile), tri-n-butyltin hydride / toluene / 4 h / 120 °C 4: 87 percent / pyridinium dichromate, 3A molecular sieves / CH₂Cl₂ / 4 h / Ambient temperature 5: 1.) 5 N sodium hydroxide, 2.) p-toluenesulfonic acid / 1.) THF, H₂O, 26 h, r. t., 2.) aq. EtOH, 60 - 65 deg C, 24 h 6: 74 percent / xylene / 36 h / 210 °C 7: 94 percent / lithium tri-tert-butoxyaluminum hydride / tetrahydrofuran / 3.5 h / Ambient temperature

Reference： [1]Andrews, Robert C.; Teague, Simon J.; Meyers, A. I. [Journal of the American Chemical Society, 1988, vol. 110, # 23, p. 7854 - 7858]

57
[ 477-47-4 ]
[ 112711-16-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / 0 °C 2: 1.) lithium hexamethyldisilazide, 2.) acetic acid / 1.) THF, 0 deg C, 40 min, 2.) THF, -78 deg C, 10 min

Reference： [1]Andrews, Robert C.; Teague, Simon J.; Meyers, A. I. [Journal of the American Chemical Society, 1988, vol. 110, # 23, p. 7854 - 7858]

58
[ 477-47-4 ]
[ 518-28-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / 0 °C 2: 1.) lithium hexamethyldisilazide, 2.) acetic acid / 1.) THF, 0 deg C, 40 min, 2.) THF, -78 deg C, 10 min 3: 79 percent / triethylammonium fluoride / acetonitrile / 72 h / Ambient temperature

Reference： [1]Andrews, Robert C.; Teague, Simon J.; Meyers, A. I. [Journal of the American Chemical Society, 1988, vol. 110, # 23, p. 7854 - 7858]

59
[ 477-47-4 ]
[ 33419-42-0 ]

Reference： [1]Chemistry Letters,1987,p. 799 - 802

60
[ 477-47-4 ]
(5R,6S,7R)-7-Chloromethyl-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: CrO₃ / pyridine / 3 h / Ambient temperature 2: t-BuOK, H₂O / 2-methyl-propan-2-ol / 0.17 h / Ambient temperature 3: HCl / CH₂Cl₂
	Multi-step reaction with 4 steps 1: CrO₃ / pyridine / 3 h / Ambient temperature 2: 10percent KOH / methanol / 30 h / Ambient temperature 3: HCl / CH₂Cl₂

Reference： [1]Feliciano, A. San; Lopez, J. L.; Medarde, M.; Corral, J. M. Miduel del; Pascual-Teresa, B. de; Puebla, P. [Tetrahedron, 1988, vol. 44, # 23, p. 7255 - 7260]
[2]Feliciano, A. San; Lopez, J. L.; Medarde, M.; Corral, J. M. Miduel del; Pascual-Teresa, B. de; Puebla, P. [Tetrahedron, 1988, vol. 44, # 23, p. 7255 - 7260]

61
[ 477-47-4 ]
[ 120090-93-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: CrO₃ / pyridine / 3 h / Ambient temperature 2: t-BuOK, H₂O / 2-methyl-propan-2-ol / 0.17 h / Ambient temperature 3: HCl / CH₂Cl₂
	Multi-step reaction with 3 steps 1: CrO₃ / pyridine / 3 h / Ambient temperature 2: 10percent KOH / methanol / 30 h / Ambient temperature 3: HCl / CH₂Cl₂

Reference： [1]Feliciano, A. San; Lopez, J. L.; Medarde, M.; Corral, J. M. Miduel del; Pascual-Teresa, B. de; Puebla, P. [Tetrahedron, 1988, vol. 44, # 23, p. 7255 - 7260]
[2]Feliciano, A. San; Lopez, J. L.; Medarde, M.; Corral, J. M. Miduel del; Pascual-Teresa, B. de; Puebla, P. [Tetrahedron, 1988, vol. 44, # 23, p. 7255 - 7260]

62
[ 477-47-4 ]
[ 120122-15-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: CrO₃ / pyridine / 3 h / Ambient temperature 2: 10percent KOH / methanol / 30 h / Ambient temperature

Reference： [1]Feliciano, A. San; Lopez, J. L.; Medarde, M.; Corral, J. M. Miduel del; Pascual-Teresa, B. de; Puebla, P. [Tetrahedron, 1988, vol. 44, # 23, p. 7255 - 7260]

63
[ 477-47-4 ]
[ 120090-94-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: CrO₃ / pyridine / 3 h / Ambient temperature 2: 10percent KOH / methanol / 30 h / Ambient temperature

Reference： [1]Feliciano, A. San; Lopez, J. L.; Medarde, M.; Corral, J. M. Miduel del; Pascual-Teresa, B. de; Puebla, P. [Tetrahedron, 1988, vol. 44, # 23, p. 7255 - 7260]

64
[ 40505-27-9 ]
[ 477-47-4 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 1308,1311
[2]Journal of the American Chemical Society,1953,vol. 75,p. 1308,1311

65
[ 4375-07-9 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ethanol; sodium acetate 2: acetone; aqueous hydrochloric acid

Reference： [1]Hartwell; Schrecker [Journal of the American Chemical Society, 1951, vol. 73, p. 2909,2916]

66
[ 477-47-4 ]
[ 477-52-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine 2: 240 °C
	With acetic anhydride at 100℃;

Reference： [1]Drake; Price [Journal of the American Chemical Society, 1951, vol. 73, p. 201,203]
[2]Location in patent: experimental part Da Silva, Rosangela; Batista, Joao Henrique Carvalho; Da Silva Maringolo, Carine; Donate, Paulo Marcos [Magnetic Resonance in Chemistry, 2009, vol. 47, # 6, p. 523 - 526]

67
[ 477-47-4 ]
[ 55568-81-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: pyridine 2: 240 °C 3: Raney nickel; ethanol / 60 °C / 73550.8 Torr / Hydrogenation

Reference： [1]Drake; Price [Journal of the American Chemical Society, 1951, vol. 73, p. 201,203]

68
[ 21606-04-2 ]
[ 477-47-4 ]
[ 1244966-30-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4503 - 4506

69
[ 4376-18-5 ]
[ 477-47-4 ]
[ 1244966-29-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃;

Reference： [1]Location in patent: scheme or table Xu, Hui; He, Xiao-Qiang [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 15, p. 4503 - 4506]

70
[ 1083302-72-0 ]
[ 477-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium carbonate / trans-di(μ-acetato)-bis[o-(di-o-tolylphosphino)benzyl]-dipalladium(II) / ethanol / 15 h / Reflux 2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / dichloromethane; water / 4 h / 20 °C 2.2: 1 h / 20 °C 3.1: sodium tetrahydroborate; methanol / 0 - 20 °C

Reference： [1]Current Patent Assignee: AXELAR AB - WO2012/30284, 2012, A1

71
[ 477-47-4 ]
C₂₈H₂₄N₂O₁₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: chromium(VI) oxide; pyridine / dichloromethane / 3 h / 20 °C 2.1: pyridine; hydroxylamine hydrochloride / ethanol / 72 h / Reflux 3.1: sodium hydride / tetrahydrofuran / 0.5 h / -10 °C 3.2: 3 h / -10 °C

Reference： [1]Wang, Yi; Shao, Yonghua; Wang, Yangyang; Fan, Lingling; Yu, Xiang; Zhi, Xiaoyan; Yang, Chun; Qu, Huan; Yao, Xiaojun; Xu, Hui [Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 34, p. 8435 - 8443]

72
[ 477-47-4 ]
C₂₈H₂₃ClN₂O₁₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: chromium(VI) oxide; pyridine / dichloromethane / 3 h / 20 °C 2.1: pyridine; hydroxylamine hydrochloride / ethanol / 72 h / Reflux 3.1: sodium hydride / tetrahydrofuran / 0.5 h / -10 °C 3.2: 3 h / -10 °C

Reference： [1]Wang, Yi; Shao, Yonghua; Wang, Yangyang; Fan, Lingling; Yu, Xiang; Zhi, Xiaoyan; Yang, Chun; Qu, Huan; Yao, Xiaojun; Xu, Hui [Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 34, p. 8435 - 8443]

73
[ 477-47-4 ]
C₂₃H₂₃NO₁₀S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: chromium(VI) oxide; pyridine / dichloromethane / 3 h / 20 °C 2.1: pyridine; hydroxylamine hydrochloride / ethanol / 72 h / Reflux 3.1: sodium hydride / tetrahydrofuran / 0.5 h / -10 °C 3.2: 48 h / 20 °C

Reference： [1]Wang, Yi; Shao, Yonghua; Wang, Yangyang; Fan, Lingling; Yu, Xiang; Zhi, Xiaoyan; Yang, Chun; Qu, Huan; Yao, Xiaojun; Xu, Hui [Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 34, p. 8435 - 8443]

74
[ 477-47-4 ]
(5aS,8aS,9R)-9-(3,4,5-Trimethoxy-phenyl)-5a,6,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione 5-oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: chromium(VI) oxide; pyridine / dichloromethane / 3 h / 20 °C 2: pyridine; hydroxylamine hydrochloride / ethanol / 72 h / Reflux

Reference： [1]Wang, Yi; Shao, Yonghua; Wang, Yangyang; Fan, Lingling; Yu, Xiang; Zhi, Xiaoyan; Yang, Chun; Qu, Huan; Yao, Xiaojun; Xu, Hui [Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 34, p. 8435 - 8443]

75
[ 477-47-4 ]
C₂₈H₂₅NO₁₀S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: chromium(VI) oxide; pyridine / dichloromethane / 3 h / 20 °C 2.1: pyridine; hydroxylamine hydrochloride / ethanol / 72 h / Reflux 3.1: sodium hydride / tetrahydrofuran / 0.5 h / -10 °C 3.2: 3 h / -10 °C

Reference： [1]Wang, Yi; Shao, Yonghua; Wang, Yangyang; Fan, Lingling; Yu, Xiang; Zhi, Xiaoyan; Yang, Chun; Qu, Huan; Yao, Xiaojun; Xu, Hui [Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 34, p. 8435 - 8443]

76
[ 477-47-4 ]
C₂₉H₂₇NO₁₀S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: chromium(VI) oxide; pyridine / dichloromethane / 3 h / 20 °C 2.1: pyridine; hydroxylamine hydrochloride / ethanol / 72 h / Reflux 3.1: sodium hydride / tetrahydrofuran / 0.5 h / -10 °C 3.2: 3 h / -10 °C

Reference： [1]Wang, Yi; Shao, Yonghua; Wang, Yangyang; Fan, Lingling; Yu, Xiang; Zhi, Xiaoyan; Yang, Chun; Qu, Huan; Yao, Xiaojun; Xu, Hui [Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 34, p. 8435 - 8443]

77
[ 477-47-4 ]
C₃₀H₂₉NO₁₀S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: chromium(VI) oxide; pyridine / dichloromethane / 3 h / 20 °C 2.1: pyridine; hydroxylamine hydrochloride / ethanol / 72 h / Reflux 3.1: sodium hydride / tetrahydrofuran / 0.5 h / -10 °C 3.2: 3 h / -10 °C

Reference： [1]Wang, Yi; Shao, Yonghua; Wang, Yangyang; Fan, Lingling; Yu, Xiang; Zhi, Xiaoyan; Yang, Chun; Qu, Huan; Yao, Xiaojun; Xu, Hui [Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 34, p. 8435 - 8443]

78
[ 477-47-4 ]
C₂₉H₂₇NO₁₁S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: chromium(VI) oxide; pyridine / dichloromethane / 3 h / 20 °C 2.1: pyridine; hydroxylamine hydrochloride / ethanol / 72 h / Reflux 3.1: sodium hydride / tetrahydrofuran / 0.5 h / -10 °C 3.2: 3 h / -10 °C

Reference： [1]Wang, Yi; Shao, Yonghua; Wang, Yangyang; Fan, Lingling; Yu, Xiang; Zhi, Xiaoyan; Yang, Chun; Qu, Huan; Yao, Xiaojun; Xu, Hui [Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 34, p. 8435 - 8443]

79
[ 477-47-4 ]
[ 6705-63-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: picropodophyllotoxin With boron trichloride In hexane at -70℃; Stage #2: With water; barium carbonate In acetone for 1h; Reflux;	3 Example 3 (3aR.4R,9R.9aS)-4.6.7-trihvdroxy-9-(3,4,5-trimethoxyphenyl)-3a,4.9.9a- tetrahvdronaphthor2,3-c1furan-1(3H)-one HO A solution of boron trichloride (BCI3, 1 ml.) 1 M in hexanes was cooled to ca -70 °C in a dry vial and PPP (100 mg, 0.24 mmol) was added over 40 minutes as a suspension in dry dichloromethane (3 ml_). The off white suspension was stirred at the same temperature for 2 hours and then transferred to Dewar with dry ice over night. The mixture was poured over ice-water (4.2 mL) and extracted once with ethyl acetate. The organic layer was washed with brine until pH 6-7, dried over Na2S04, filtered and evaporated. The solid material was suspended in water: acetone: barium carbonate (1mL: 1ml_: 67 mg) and refluxed for an hour. The precipitate was filtered off and the pH of the filtrate was adjusted to 2-3 by 1 M hydrochloric acid and extracted five times with ethyl acetate. The combined organic layers were washed with brine until the pH was 6 again, dried over Na2S04 and evaporated to afford 16 mg of the crude product. The crude product was used as such.

Reference： [1]Current Patent Assignee: AXELAR AB - WO2013/132263, 2013, A1 Location in patent: Page/Page column 14

80
[ 109-52-4 ]
[ 477-47-4 ]
[ 1093351-66-6 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 4.5h;	3 Example 3 (5R,5aR,8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5.5a,6,8,8a.9- hexahvdrofuror3',4':6.71naphthor2,3-diri,31dioxol-5-yl pentanoate Example 3 (5R,5aR,8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5.5a,6,8,8a.9- hexahvdrofuror3',4':6.71naphthor2,3-diri,31dioxol-5-yl pentanoate PPP (41 mg, 0.10 mmol), DMAP (6 mg, 0.05 mmol) and valeric acid (12 mg, 0.12 mmol) were weighed in a vial. Dry dichloromethane (1.5 mL) was added followed by EDC-HCI (25 mg, 0.13 mmol) at room temperature. The reaction mixture was stirred for 4.5 hours. Then more dichloromethane was added and the solution was washed with 0.1 M HCI, saturated NaHC03 and brine. The organic layer was dried and evaporated to give the product in 43 mg yield and 87% purity LCMS (ACE 3 C8, 50 x 3.0 mm, 10% to 97% acetonitrile in 3 min in 0.1% TFA in water, 1 mL/min), MS ESI+ m/z 397, rt 2.506.

Reference： [1]Current Patent Assignee: AXELAR AB - WO2013/132262, 2013, A1 Location in patent: Page/Page column 19

81
[ 111-14-8 ]
[ 477-47-4 ]
[ 1453805-80-5 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 72h;	4 Example 4 (5R,5aR,8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9- hexahydrofuror3'.4':6.7^rlnaphthor2,3-diri.31dioxol-5-yl heptanoate Example 4 (5R,5aR,8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9- hexahydrofuror3'.4':6.7rlnaphthor2,3-diri.31dioxol-5-yl heptanoate PPP (41 mg, 0.10 mmol), DMAP (6 mg, 0.05 mmol) and heptanoic acid (16 mg, 0.12 mmol) were weighed in a vial. Dry dichloromethane (1.5 ml_) was added followed by EDC- HCI (25 mg, 0.13 mmol) at room temperature. The reaction mixture was stirred for three days. Then more dichloromethane was added and the solution was washed with 0.1 M HCI, saturated NaHC03 and brine. The crude product (54 mg) was purified by flash chromatography using 0-4% methanol in dichloromethane to give the product in 42 mg yield and 91% purity LCMS (ACE 3 C8, 50 x 3.0 mm, 10% to 97% acetonitrile in 3 min in 0.1% TFA in water, 1 mUmin), MS ESI+ m/z 397, rt 2.687.

Reference： [1]Current Patent Assignee: AXELAR AB - WO2013/132262, 2013, A1 Location in patent: Page/Page column 19; 20

82
[ 112-37-8 ]
[ 477-47-4 ]
[ 1453805-81-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 72h;	Example 5 (5R.5aR.8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9- hexahvdrofuror3',4':6,71naphthor2,3-diri,31dioxol-5-yl undecanoate PPP (41 mg, 0.1 mmol), DMAP (6 mg, 0.05 mmol) and the undecanoic (23 mg, 0.09 mmol) acid were weighed in a vial. Dry dichloromethane (1.5 mL) was added and EDC- HCI (23 mg, 0.12 mmol) was added at room temperature. The reaction mixture was stirred for three days. More dichloromethane was added and the solution was washed with 0.1 M HCI (aq), saturated NaHC03 and brine. The crude product (55 mg) was purified by flash chromatography using 2-4% methanol in dichloromethane to give the title compound in 77% yield (45 mg) and 96% purity according to LCMS (ACE 3 C8, 50 x 3.0 mm, 10% to 97% acetonitrile in 3 min in 0.1% TFA in water, 1 mL/min), MS ESI+ m/z 397, rt 3.107.

Reference： [1]Patent: WO2013/132262,2013,A1 .Location in patent: Page/Page column 20

83
[ 57-10-3 ]
[ 477-47-4 ]
[ 1453805-82-7 ]

Yield	Reaction Conditions	Operation in experiment
38 mg	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	6 Example 6 (5R.5aR,8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5.5a,6,8,8a,9- hexahvdrofuror3'.4':6.71naphthor2,3-din.31dioxol-5-vi palmitate Example 6 (5R.5aR,8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5.5a,6,8,8a,9- hexahvdrofuror3'.4':6.71naphthor2,3-din.31dioxol-5-vi palmitate PPP (41 mg, 0.10 mmol), DMAP (6 mg, 0.05 mmol) and palmitic acid (23 mg, 0.09 mmol) were weighed in a vial. Dry dichloromethane was added followed by EDC-HCI (23 mg, 0.12 mmol) at room temperature. The reaction mixture was stirred overnight. More dichloromethane was added and the solution was washed with 0.1 M HCI, saturated NaHC03 and brine. The crude product (54 mg) was purified by flash chromatography (1.5 x 5 cm) using 1% methanol in dichloromethane to give the title product in 38 mg yield and 100% purity according to LCMS (ACE 3 C8, 50 x 3.0 mm, 10% to 97% acetonitrile in 3 min in 0.1% TFA in water, 1 mL/min), MS ESI+ m/z 397, rt 2.104.

Reference： [1]Current Patent Assignee: AXELAR AB - WO2013/132262, 2013, A1 Location in patent: Page/Page column 21

84
[ 141-82-2 ]
[ 477-47-4 ]
[ 1453805-83-8 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 96h;	7 Example 7 3-oxo-3-(((5R,5aR.8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5.5a,6,8,8a,9- hexahvdrofuror3',4':6,71naphthor2,3-diri.31dioxol-5-yl)oxy)propanoic acid Example 7 3-oxo-3-(((5R,5aR.8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5.5a,6,8,8a,9- hexahvdrofuror3',4':6,71naphthor2,3-diri.31dioxol-5-yl)oxy)propanoic acid PPP (41 mg, 0.10 mmol), DMAP (6 mg, 0.05 mmol) and malonic acid (11 mg, 0.1 mmol) were weighed in a vial. Dry dichloromethane (1.5 ml.) was added followed by EDC-HCI (19 mg, 0.1 mmol) at room temperature. The reaction mixture was stirred for 4 days. Then more dichloromethane was added and the solution was washed with 0.1 M HCI, saturated NaHC03 and brine. The crude product (39 mg) was purified by flash chromatography using 2% methanol in dichloromethane as eluent to give the product in 15 mg yield and 94% purity LCMS (ACE 3 C8, 50 x 3.0 mm, 10% to 97% acetonitrile in 3 min in 0.1% TFA in water, 1 mL/min), MS ESI+ m/z 397, rt 2.082.

Reference： [1]Current Patent Assignee: AXELAR AB - WO2013/132262, 2013, A1 Location in patent: Page/Page column 21; 22

85
[ 123-99-9 ]
[ 477-47-4 ]
[ 1453805-84-9 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	8 Example 8 9-oxo-9-f((5R,5aR,8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9- hexahvdrofuror3'.4':6,71naphthor2,3-diri,31dioxol-5-yl)oxy)nonanoic acid Example 8 9-oxo-9-f((5R,5aR,8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9- hexahvdrofuror3'.4':6,71naphthor2,3-diri,31dioxol-5-yl)oxy)nonanoic acid PPP (41 mg, 0.10 mmol), DMAP (6 mg, 0.05 mmol) and azelaic acid (17 mg, 0.09 mmol) were weighed in a vial. Dry dichloromethane was added followed by EDC-HCI (17 mg, 0.09 mmol) at room temperature. The reaction mixture was stirred overnight. More dichloromethane was added and the solution was washed with 0.1 M HCI, saturated NaHC03 and brine. The crude product (49 mg) was purified by flash chromatography using methanol : dichloromethane 1 : 40 and 1 : 20 to give the product in 20 mg yield and 90% purity according to LCMS (ACE 3 C8, 50 x 3.0 mm, 10% to 97% acetonitrile in 3 min in 0.1% TFA in water, 1 mL/min), MS ESI+ m/z 397, rt 1.585

Reference： [1]Current Patent Assignee: AXELAR AB - WO2013/132262, 2013, A1 Location in patent: Page/Page column 22

86
[ 123-99-9 ]
[ 477-47-4 ]
[ 1453805-95-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 72h;	19 Example 19 bis((5R.5aR.8aS,9R)-8-oxo-9-(3A5-trimethoxyphenyl)-5,5a,6,8,8a.9- hexahvdrofuror3'.4':6,71naphthor2,3-cnri.31dioxol-5-yl) nonanedioate Example 19 bis((5R.5aR.8aS,9R)-8-oxo-9-(3A5-trimethoxyphenyl)-5,5a,6,8,8a.9- hexahvdrofuror3'.4':6,71naphthor2,3-cnri.31dioxol-5-yl) nonanedioate PPP (41 mg, 0.10 mmol), DMAP (6 mg, 0.05 mmol) and azelaic acid (9 mg, 0.05 mmol) were weighed in a vial. Dry dichloromethane (1.5 ml_) was added followed by EDC-HCI (23 mg, 0.12 mmol) at room temperature. The reaction mixture was stirred for three days. More dichloromethane was added and the solution was washed with 0.1 M HCI, saturated NaHC03 and brine. The crude product (55 mg) was purified by flash chromatography using Methanol: dichloromethane 1 : 25 to give the title product in 22 mg yield and 94% purity according to LCMS (ACE 3 C8, 50 x 3.0 mm, 10% to 97% acetonitrile in 3 min in 0.1 % TFA in water, 1 mUmin), MS ESI+ m/z 397, rt 2.720.

Reference： [1]Current Patent Assignee: AXELAR AB - WO2013/132262, 2013, A1 Location in patent: Page/Page column 32

87
[ 29022-11-5 ]
[ 477-47-4 ]
[ 1453805-85-0 ]

Yield	Reaction Conditions	Operation in experiment
45%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3.5h;	9 Example 9 (5R.5aR.8aS.9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9- hexahvdrofuror3'.4';6.71naphthor2.3-cnri.31dioxol-5-yl 2-((((9H-fluoren-9- yl)methoxy)carbonyl)amino)acetate Example 9 (5R.5aR.8aS.9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9- hexahvdrofuror3'.4';6.71naphthor2.3-cnri.31dioxol-5-yl 2-((((9H-fluoren-9- yl)methoxy)carbonyl)amino)acetate PPP (82 mg, 0.20 mmol), DMAP (12 mg, 0.1 mmol) and FMOC-glycine (60 mg, 0.2 mmol) were dissolved in dry dichloromethane (3 mL) and EDC-HCI (52 mg, 0.26 mmol) was added at room temperature. The reaction mixture was stirred for 3.5 hours. Then more dichloromethane was added and the solution was washed with 0.1 M HCI, saturated NaHC03 and brine. The crude product (141 mg) was purified by flash chromatography using 2% methanol in dichloromethane to give the product in 45% yield (62 mg) and >99% purity according to LCMS (ACE 3 C8, 50 x 3.0 mm, 10% to 97% acetonitrile in 3 min in 0.1% TFA in water, 1 mL/min), MS ESI+ m/z 397, rt 2.588.

Reference： [1]Current Patent Assignee: AXELAR AB - WO2013/132262, 2013, A1 Location in patent: Page/Page column 23

88
[ 126727-02-4 ]
[ 477-47-4 ]
(5R,5aR,8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methylbutanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 6h;	11 Example 11 (R>-f5R.5aR.8aS.9R)-8-oxo-9-f3.4.5-trimethoxyphenyl)-5,5a,6,8,8a.9- θΧΒΗνιΓθυΓθΓβ'^^β.ΤΙ^ηΒρΗΗοΓΣ.Β-ΓΙ^ΙαοχοΙ-β-νΙ 2-((((9H-fluoren-9- yl)methoxy)carbonyl)amino)-3-methylbutanoate Example 11 (R>-f5R.5aR.8aS.9R)-8-oxo-9-f3.4.5-trimethoxyphenyl)-5,5a,6,8,8a.9- θΧΒΗνιΓθυΓθΓβ'^^β.ΤΙηΒρΗΗοΓΣ.Β-ΓΙ^ΙαοχοΙ-β-νΙ 2-((((9H-fluoren-9- yl)methoxy)carbonyl)amino)-3-methylbutanoate PPP (62 mg, 0.15 mmol), DMAP (9 mg, 0.08 mmol) and FMOC-valine (51 mg, 0.15 mmol) were weighed in a vial. Dry dichloromethane (2.25 ml_) was added followed by EDC-HCI (38 mg, 0.2 mmol) at room temperature. The reaction mixture was stirred for 6 hours. Then more dichloromethane was added and the solution was washed with 0.1 M HCI, saturated NaHC03 and brine. The crude product (117 mg) was purified by flash chromatography using 2% methanol in dichloromethane as eluent to give the product (96 mg) in 87% yield and in 94% purity LCMS (ACE 3 C8, 50 x 3.0 mm, 10% to 97% acetonitrile in 3 min in 0.1% TFA in water, 1 mlJmin), MS ESI+ m/z 397, rt 2.755.

Reference： [1]Current Patent Assignee: AXELAR AB - WO2013/132262, 2013, A1 Location in patent: Page/Page column 25

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	477-47-4	MDL No. :	MFCD01742647
Formula :	C₂₂H₂₂O₈	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YJGVMLPVUAXIQN-HAEOHBJNSA-N
M.W :	414.41	Pubchem ID :	72435
Synonyms :	Picropodophyllotoxin;AXL1717;NSC 36407;PPP	Chemical Name :	(5R,5aS,8aR,9R)-9-Hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one

Num. heavy atoms :	30
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.41
Num. rotatable bonds :	4
Num. H-bond acceptors :	8.0
Num. H-bond donors :	1.0
Molar Refractivity :	103.85
TPSA :	92.68 Å²

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-7.4 cm/s

[ CAS No. 477-47-4 ] {[proInfo.proName]}

Quality Control of [ 477-47-4 ]

Related Doc. of [ 477-47-4 ]

Product Details of [ 477-47-4 ]

Calculated chemistry of [ 477-47-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 477-47-4 ]

Application In Synthesis of [ 477-47-4 ]

[ 477-47-4 ] Synthesis Path-Upstream 1~1

[ 477-47-4 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Log Po/w (iLOGP) :	3.2
Log Po/w (XLOGP3) :	2.01
Log Po/w (WLOGP) :	2.08
Log Po/w (MLOGP) :	1.43
Log Po/w (SILICOS-IT) :	2.9
Consensus Log Po/w :	2.32

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

Log S (ESOL) :	-3.71
Solubility :	0.0812 mg/ml ; 0.000196 mol/l
Class :	Soluble
Log S (Ali) :	-3.58
Solubility :	0.108 mg/ml ; 0.000261 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.75
Solubility :	0.00734 mg/ml ; 0.0000177 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.64

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P280-P301+P310-P305+P351+P338	UN#:	3462
Hazard Statements:	H301-H312-H315-H319-H335	Packing Group:	Ⅱ
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