Name: 2144-40-3|(cis-Tetrahydrofuran-2,5-diyl)dimethanol|80%
Brand: Ambeed
SKU: A609454
Price: 45.0 USD
Availability: InStock
Rating: 90 (32 reviews)

1
[ 67-47-0 ]
[ 2144-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	With diethyl ether; nickel at 160℃; Hydrogenation;
	With methanol; nickel at 160℃; Hydrogenation;

Reference： [1]Cope; Baxter [Journal of the American Chemical Society, 1955, vol. 77, p. 393,395] Haworth et al. [Journal of the Chemical Society, 1945, p. 1,3]
[2]Turner et al. [Analytical Chemistry, 1954, vol. 26, p. 898]

2
[ 1472-01-1 ]
[ 2144-40-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With lithium aluminium tetrahydride In diethyl ether for 12h; Heating;
	With tetrahydrofuran; lithium aluminium tetrahydride

Reference： [1]Nakazaki, Masao; Naemura, Koichiro; Makimura, Masaru; Matsuda, Atsushi; Kawano, Takaaki; Ohta, Yoshihiro [Journal of Organic Chemistry, 1982, vol. 47, # 12, p. 2429 - 2435]
[2]Cope; Baxter [Journal of the American Chemical Society, 1955, vol. 77, p. 393,395]

3
[ 2144-40-3 ]
[ 64-19-7 ]
[ 98559-48-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide

Reference： [1]Gryszkiewicz-Trochimowski et al. [Bulletin de la Societe Chimique de France, 1958, p. 610,615]

4
[ 2144-40-3 ]
[ 98-59-9 ]
[ 1472-00-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	With dmap; triethylamine In tetrahydrofuran at 0 - 20℃;	7.1 Step 1. Step 1. (cis-tetrahydrofuran-2,5-diyl)bis(methylene) bis(4-methylbenzenesulfonate) (7-2a) To a stirred solution of cis-2,5-bishydroxymethyl-tetrahydrofuran (7-1a, 263 mg, 1.99 mmol) and DMAP (24 mg, 0.20 mmol) in THF (7 mL) was added Et3N (1.3 mL, 9.3 mmol) and the resulting mixture was cooled to 0° C. Tosyl chloride (835 mg, 4.38 mmol) was added and the resulting mixture was allowed to warm to room temperature and then stirred overnight. The reaction mixture was then diluted with water (25 mL) and EtOAc (150 mL) was added. The organic layer was then washed with water (25 mL), sat. aq. NaHCO3 (30 mL), and brine (30 mL), dried over MgSO4, filtered, and concentrated to dryness. The crude material was purified by silica gel chromatography eluting with 0% to 60% EtOAc in heptane to afford the 7-2a as a white solid (488.6 mg, 1.098 mmol, 55% yield). MS [M+H2O]+=458.4. 1H NMR (400 MHz, DCM-d2) δ 7.87-7.73 (m, 4H), 7.48-7.37 (m, 4H), 4.10 (dddd, J=11.1, 6.4, 4.3, 1.9 Hz, 2H), 4.02-3.85 (m, 4H), 2.49 (s, 6H), 2.07-1.91 (m, 2H), 1.76-1.61 (m, 2H).
	With pyridine
1.23 g	With pyridine at 0℃;

With pyridine at 0 - 20℃; for 18h;

To a mechanically stirred suspension of silica-supported NaIO4 (240 g) in THF (1260 mL) and CH2Cl2 (138 mL) at 0° C. was added 1,5-hexadiene (8.5 mL) followed by addition in drops of a 0.01 M aqueous solution of RuCl3 (14.4 mL). After 1.5 h, iPrOH (300 mL) was added. Stir 10 min, then filter, wash silica with EtOAc and concentrate filtrate. Pass oil through silica gel eluting with Et2O, EtOAc and 5% MeOH/CHCl3. Yields a clear oil (9.5 g). This material was dissolved in pyridine (90 mL) at 0° C. A solution of TsCl (31 g) in pyridine (36 mL) was added in drops. Allow to warm to RT. After 18 h H2O (300 mL) was added. The white solid was collected by filtration and dried (12 g). This material in toluene (60 mL) was treated with benzylamine (10 mL). Heat at reflux for 18 h. Filter and concentrate in vacuo. Purify by vacuum distillation (5.7 g). This compound (7.3 g) in 1,2-dichloroethane (150 mL) was treated with 1-chloroethyl chloroformate (12 mL) and K2CO3 (15 g) and heated at reflux overnight. Filter using CH2Cl2. Concentrate, take up in EtOH and add 12 N HCl (5 mL). Concentrate. Add acetone and filter (4.5 g).

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - US2020/17461, 2020, A1 Location in patent: Paragraph 1390-1391
[2]Newth; Wiggins [Journal of the Chemical Society, 1948, p. 155,157] Cope; Baxter [Journal of the American Chemical Society, 1955, vol. 77, p. 393,395]
[3]Schiavo, V.; Descotes, G.; Mentech, J. [Bulletin de la Societe Chimique de France, 1991, # 5, p. 704 - 711]
[4]Current Patent Assignee: PFIZER INC - US2009/98086, 2009, A1 Location in patent: Page/Page column 63

5
[ 2144-40-3 ]
[ 89581-01-1 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; thionyl chloride

Reference： [1]Cope; Anderson [Journal of the American Chemical Society, 1955, vol. 77, p. 995,997] Newth; Wiggins [Journal of the Chemical Society, 1948, p. 155,157] Cope; Baxter [Journal of the American Chemical Society, 1955, vol. 77, p. 393,395]

6
[ 99974-69-3 ]
[ 2144-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrahydrofuran; lithium aluminium tetrahydride

Reference： [1]Gryszkiewicz-Trochimowski et al. [Bulletin de la Societe Chimique de France, 1958, p. 610,615]

7
[ 67-47-0 ]
[ 1883-75-6 ]
[ 2144-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In water at 140℃; different temperatures, pressures, reaction times and concentrations of catalyst, other catalysts;
1: 71 %Spectr. 2: 28 %Spectr.	With bis(acetato){2,2'-bis(diphenylphosphino)-1,1'-binaphthyl}ruthenium(II); hydrogen In toluene at 120℃; for 16h;

Reference： [1]Schiavo, V.; Descotes, G.; Mentech, J. [Bulletin de la Societe Chimique de France, 1991, # 5, p. 704 - 711]
[2]Cadu, Alban; Sekine, Kohei; Mormul, Jaroslaw; Ohlmann, Dominik M.; Schaub, Thomas; Hashmi, A. Stephen K. [Green Chemistry, 2018, vol. 20, # 14, p. 3386 - 3393]

8
[ 67-47-0 ]
[ 2144-40-3 ]
trans-2,5-bis-hydroxymethyltetrahydrofurane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80 % Chromat.	With hydrogen In water at 140℃; for 0.5h;
64.912 % de	With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); hydrogen; [(4S)-4-[5-bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphanyl-1,3-benzodioxol-4-yl]-4,5,6,7-tetrahydro-1,3-benzodioxol-5-yl]-bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphane In toluene at 120℃; for 16h; Overall yield = 87 %Spectr.;

Reference： [1]Schiavo, V.; Descotes, G.; Mentech, J. [Bulletin de la Societe Chimique de France, 1991, # 5, p. 704 - 711]
[2]Cadu, Alban; Sekine, Kohei; Mormul, Jaroslaw; Ohlmann, Dominik M.; Schaub, Thomas; Hashmi, A. Stephen K. [Green Chemistry, 2018, vol. 20, # 14, p. 3386 - 3393]

9
[ 1883-75-6 ]
[ 2144-40-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With Raney Ni (W-5); hydrogen In ethanol at 100℃;

Reference： [1]Naemura; Fukuda; Takahashi; Konishi; Hirose; Tobe [Tetrahedron Asymmetry, 1993, vol. 4, # 5, p. 911 - 918]

10
[ 2144-40-3 ]
[ 112-96-9 ]
cis-2-(octadecylaminocarbonyloxymethyl)-5-hydroxymethyltetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With pyridine at 60℃; for 15h;

Reference： [1]Tsuri; Haga; Matsui; Kamata; Kakushi; Uchida [Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 1, p. 75 - 84]

11
[ 2144-40-3 ]
[ 20445-31-2 ]
(S,R)-tetrahydrofuran-2,5-dimethanol, bis-Mosher's ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h; Heating;

Reference： [1]Jung, Michael E.; Trifunovich, Ivan D.; Sledeski, Adam W. [Heterocycles, 1993, vol. 35, # 1, p. 273 - 280]

12
[ 2144-40-3 ]
[ 79-03-8 ]
[ 119873-52-8 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In diethyl ether

Reference： [1]Naemura, Koichiro; Takahashi, Nobuo; Chikamatsu, Hiroaki [Chemistry Letters, 1988, # 10, p. 1717 - 1720]

13
[ 2144-40-3 ]
[ 3282-30-2 ]
[ 119873-54-0 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In diethyl ether

Reference： [1]Naemura, Koichiro; Takahashi, Nobuo; Chikamatsu, Hiroaki [Chemistry Letters, 1988, # 10, p. 1717 - 1720]

14
[ 2144-40-3 ]
[ 108-24-7 ]
[ 119873-51-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With pyridine for 24h; Ambient temperature;
12%	With dmap In dichloromethane at 25℃;

Reference： [1]Naemura; Fukuda; Takahashi; Konishi; Hirose; Tobe [Tetrahedron Asymmetry, 1993, vol. 4, # 5, p. 911 - 918]
[2]Mueller, Christian E.; Zell, Daniela; Hrdina, Radim; Wende, Raffael C.; Wanka, Lukas; Schuler, Soeren M. M.; Schreiner, Peter R. [Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8465 - 8484]

15
[ 2144-40-3 ]
[ 88868-31-9 ]
[ 88868-15-9 ]

Yield	Reaction Conditions	Operation in experiment
27.3%	With sodium hydride In tetrahydrofuran for 48h; Heating;

Reference： [1]Artz,S.P.; Cram,D.J. [Journal of the American Chemical Society, 1984, vol. 106, p. 2160]

16
[ 2144-40-3 ]
[ 123308-33-8 ]
[ 123292-14-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In tetrahydrofuran for 42h; Heating; Yield given;

Reference： [1]Tucker; Knobler; Goldberg; Cram [Journal of Organic Chemistry, 1989, vol. 54, # 23, p. 5460 - 5482]

17
[ 2144-40-3 ]
[ 123291-88-3 ]
[ 123292-07-9 ]

Yield	Reaction Conditions	Operation in experiment
33%	With sodium hydride In tetrahydrofuran for 42h; Heating;

Reference： [1]Tucker; Knobler; Goldberg; Cram [Journal of Organic Chemistry, 1989, vol. 54, # 23, p. 5460 - 5482]

18
[ 2144-40-3 ]
[ 122383-85-1 ]
[ 122383-79-3 ]

Yield	Reaction Conditions	Operation in experiment
19%	With sodium hydride In tetrahydrofuran for 10h; Heating;

Reference： [1]Helgeson, Roger C.; Czech, Bronislaw P.; Chapoteau, Eddy; Gebauer, Carl R.; Kumar, Anand; Cram, Donald J. [Journal of the American Chemical Society, 1989, vol. 111, # 16, p. 6339 - 6350]

19
[ 2144-40-3 ]
[ 122110-94-5 ]
(20R,23S)-14,29-Dimethyl-31,33,34,35-tetraethoxy-4-(2,4,6-trinitroanilino)-18,25,32-trioxahexacyclo<25.3.1.1^2,6.1^7,11.1^12,16.1^20,23>pentatriaconta-1(31),2,4,6(35),7,9,11(34),12,14,16(33),27,29-dodecaene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In tetrahydrofuran for 10h; Heating; Yield given;

Reference： [1]Helgeson, Roger C.; Czech, Bronislaw P.; Chapoteau, Eddy; Gebauer, Carl R.; Kumar, Anand; Cram, Donald J. [Journal of the American Chemical Society, 1989, vol. 111, # 16, p. 6339 - 6350]

20
[ 2144-40-3 ]
[ 75-36-5 ]
[ 119873-51-7 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In diethyl ether

Reference： [1]Naemura, Koichiro; Takahashi, Nobuo; Chikamatsu, Hiroaki [Chemistry Letters, 1988, # 10, p. 1717 - 1720]

21
[ 2144-40-3 ]
[ 79-30-1 ]
[ 119873-53-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In diethyl ether

Reference： [1]Naemura, Koichiro; Takahashi, Nobuo; Chikamatsu, Hiroaki [Chemistry Letters, 1988, # 10, p. 1717 - 1720]

22
[ 2144-40-3 ]
[ 141-75-3 ]
[ 128365-66-2 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane Ambient temperature;

Reference： [1]Estermann; Prasad; Shapiro; Repic; Hardtmann; Bolsterli; Walkinshaw [Tetrahedron Letters, 1990, vol. 31, # 4, p. 445 - 448]

23
[ 2144-40-3 ]
[ 88868-28-4 ]
[ 88928-99-8 ]

Yield	Reaction Conditions	Operation in experiment
24.4%	With sodium hydride In tetrahydrofuran for 48h; Heating;

Reference： [1]Artz,S.P.; Cram,D.J. [Journal of the American Chemical Society, 1984, vol. 106, p. 2160]

24
[ 2144-40-3 ]
[ 122-79-2 ]
(2R,5S)-(-)-2-(acetoxymethyl)-5-(hydroxymethyl)tetrahydofuran [ No CAS ]
(2S,5R)-(+)-2-(acetoxymethyl)-5-(hydroxymethyl)tetrahydofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lipase YS from Pseudomonas sp In cyclohexane for 1.5h; Ambient temperature; other 2,5-disubstituted tetrahydrofuran derivatives and acylating agents; asymmetric esterification;
	In cyclohexane for 1.5h; Ambient temperature; lipase YS from Pseudomonas sp.; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Reference： [1]Naemura; Fukuda; Takahashi; Konishi; Hirose; Tobe [Tetrahedron Asymmetry, 1993, vol. 4, # 5, p. 911 - 918]
[2]Naemura; Fukuda; Takahashi; Konishi; Hirose; Tobe [Tetrahedron Asymmetry, 1993, vol. 4, # 5, p. 911 - 918]

25
[ 590-28-3 ]
[ 2144-40-3 ]
[ 112-89-0 ]
cis-2-(octadecylaminocarbonyloxymethyl)-5-hydroxymethyltetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	In acetonitrile at 100℃; for 20h; analogous reaction with and without other phase-transfer catalysts; analogous reaction of other diols;
69%	In acetonitrile at 100℃; for 20h; analogous reaction with other alcohols; analogous reation without and with other phase-transfer catalysts;
69%	In acetonitrile at 100℃; for 20h;

Reference： [1]Prashad, Mahavir; Tomesch, John C.; Houlihan, William [Synthesis, 1990, # 6, p. 477 - 480]
[2]Prashad, Mahavir; Tomesch, John C.; Houlihan, William [Synthesis, 1990, # 6, p. 477 - 480]
[3]Prashad, Mahavir; Tomesch, John C.; Houlihan, William [Synthesis, 1990, # 6, p. 477 - 480]

26
[ 592-42-7 ]
[ 2144-40-3 ]
[ 58029-27-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 8% 2: 20%	With potassium permanganate; carbon dioxide In water; acetone at -10℃; pH 6;
1: 20% 2: 20%	With potassium permanganate; carbon dioxide In water; acetone at -10℃; pH 6;

Reference： [1]Wolf, Saul; Ingold, Christopher F. [Journal of the American Chemical Society, 1981, vol. 103, # 4, p. 940 - 941]
[2]Wolf, Saul; Ingold, Christopher F. [Journal of the American Chemical Society, 1981, vol. 103, # 4, p. 940 - 941]

27
[ 108-24-7 ]
[ 119873-51-7 ]
[ 2144-40-3 ]
(+/-)-cis-2-(acetoxymethyl)-5-(hydroxymethyl)tetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 25% 2: 33%	With pyridine; acetic anhydride for 24h; Ambient temperature;

Reference： [1]Naemura; Fukuda; Takahashi; Konishi; Hirose; Tobe [Tetrahedron Asymmetry, 1993, vol. 4, # 5, p. 911 - 918]

28
β-2,5-anhydro-6-O-benzoyl-3,4-dideoxygluconic acid [ No CAS ]
[ 2144-40-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With lithium aluminium tetrahydride In tetrahydrofuran Heating;

Reference： [1]Jung, Michael E.; Trifunovich, Ivan D.; Sledeski, Adam W. [Heterocycles, 1993, vol. 35, # 1, p. 273 - 280]

29
[ 2144-40-3 ]
[ 51762-67-5 ]
cis-2,5-bis(2',3'-dicyanophenoxymethyl)tetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With potassium carbonate In dimethyl sulfoxide for 240h; Ambient temperature;

Reference： [1]Leznoff; Drew [Canadian Journal of Chemistry, 1996, vol. 74, # 3, p. 307 - 318]

30
[ 2144-40-3 ]
[ 98-59-9 ]
Toluene-4-sulfonic acid (2S,5R)-5-hydroxymethyl-tetrahydro-furan-2-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane for 4h; Ambient temperature;

Reference： [1]Conti, Paola; Dallanoce, Clelia; De Amici, Marco; De Micheli, Carlo; Carrea, Giacomo; Zambianchi, Francesca [Tetrahedron Asymmetry, 1998, vol. 9, # 4, p. 657 - 665]

32
[ 67-47-0 ]
[ 60-29-7 ]
[ 2144-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	at 160℃; Hydrogenation;

Reference： [1]Cope; Baxter [Journal of the American Chemical Society, 1955, vol. 77, p. 393,395] Haworth et al. [Journal of the Chemical Society, 1945, p. 1,3]

33
[ 592-42-7 ]
[ 2144-40-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium periodate In tetrahydrofuran; dichloromethane at 0℃;
60%	With osmium(VIII) oxide; trimethylamine-N-oxide; camphor-10-sulfonic acid In dichloromethane
5%	With tetrapropylammonium perruthennate; acetic acid; 4-methylmorpholine N-oxide In dichloromethane at 20℃;

	With silica-supported sodium periodate In tetrahydrofuran; dichloromethane; water at 0℃; for 1.5h;	To a mechanically stirred suspension of silica-supported NaIO4 (240 g) in THF (1260 mL) and CH2Cl2 (138 mL) at 0° C. was added 1,5-hexadiene (8.5 mL) followed by addition in drops of a 0.01 M aqueous solution of RuCl3 (14.4 mL). After 1.5 h, iPrOH (300 mL) was added. Stir 10 min, then filter, wash silica with EtOAc and concentrate filtrate. Pass oil through silica gel eluting with Et2O, EtOAc and 5% MeOH/CHCl3. Yields a clear oil (9.5 g). This material was dissolved in pyridine (90 mL) at 0° C. A solution of TsCl (31 g) in pyridine (36 mL) was added in drops. Allow to warm to RT. After 18 h H2O (300 mL) was added. The white solid was collected by filtration and dried (12 g). This material in toluene (60 mL) was treated with benzylamine (10 mL). Heat at reflux for 18 h. Filter and concentrate in vacuo. Purify by vacuum distillation (5.7 g). This compound (7.3 g) in 1,2-dichloroethane (150 mL) was treated with 1-chloroethyl chloroformate (12 mL) and K2CO3 (15 g) and heated at reflux overnight. Filter using CH2Cl2. Concentrate, take up in EtOH and add 12 N HCl (5 mL). Concentrate. Add acetone and filter (4.5 g).
	With ruthenium tetroxide
	Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 20 °C 2: sodium hydroxide / water / 16 h / 20 °C

Reference： [1]Roth, Stefanie; Goehler, Sabrina; Cheng, Huan; Stark, Christian B. W. [European Journal of Organic Chemistry, 2005, # 19, p. 4109 - 4118]
[2]Donohoe, Timothy J.; Butterworth, Sam [Angewandte Chemie - International Edition, 2003, vol. 42, # 8, p. 948 - 951]
[3]Piccialli, Vincenzo; Caserta, Teresa [Tetrahedron Letters, 2004, vol. 45, # 2, p. 303 - 308]
[4]Current Patent Assignee: PFIZER INC - US2009/98086, 2009, A1 Location in patent: Page/Page column 63
[5]Location in patent: body text Piccialli, Vincenzo; Zaccaria, Sabrina; Oliviero, Giorgia; D'Errico, Stefano; D'Atri, Valentina; Borbone, Nicola [European Journal of Organic Chemistry, 2012, # 23, p. 4293 - 4305]
[6]Qayed, Wesam S.; Luzzio, Frederick A. [Letters in Organic Chemistry, 2015, vol. 12, # 9, p. 622 - 630]

34
[ 592-42-7 ]
[ 2144-40-3 ]
trans-2,5-bis-hydroxymethyltetrahydrofurane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ruthenium trichloride In tetrahydrofuran; dichloromethane; water at 0℃; Title compound not separated from byproducts.;

Reference： [1]Goehler, Sabrina; Roth, Stefanie; Cheng, Huan; Goeksel, Huelya; Rupp, Alexander; Haustedt, Lars O.; Stark, Christian B. W. [Synthesis, 2007, # 17, p. 2751 - 2754]

35
[ 2144-40-3 ]
[ 41869-03-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 44 percent / n-Bu₄NHSO₄, aq. NaOH / CH₂Cl₂ / 4 h / Ambient temperature 2: 85 percent / Et₃N / CH₂Cl₂ / 0 °C 3: 79 percent / NaI / butan-2-one / Heating 5: LiAlH₄ / diethyl ether / 2 h / Heating

Reference： [1]Conti, Paola; Dallanoce, Clelia; De Amici, Marco; De Micheli, Carlo; Carrea, Giacomo; Zambianchi, Francesca [Tetrahedron Asymmetry, 1998, vol. 9, # 4, p. 657 - 665]

36
[ 2144-40-3 ]
[ 36842-37-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 44 percent / n-Bu₄NHSO₄, aq. NaOH / CH₂Cl₂ / 4 h / Ambient temperature 2: 85 percent / Et₃N / CH₂Cl₂ / 0 °C 3: 79 percent / NaI / butan-2-one / Heating 5: LiAlH₄ / diethyl ether / 2 h / Heating 6: Et₃N / diethyl ether / 20 h / Ambient temperature 7: 70 percent / methanol / 5 h / 100 °C

Reference： [1]Conti, Paola; Dallanoce, Clelia; De Amici, Marco; De Micheli, Carlo; Carrea, Giacomo; Zambianchi, Francesca [Tetrahedron Asymmetry, 1998, vol. 9, # 4, p. 657 - 665]

37
[ 2144-40-3 ]
[ 210469-20-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 44 percent / n-Bu₄NHSO₄, aq. NaOH / CH₂Cl₂ / 4 h / Ambient temperature 2: 85 percent / Et₃N / CH₂Cl₂ / 0 °C 3: 79 percent / NaI / butan-2-one / Heating 5: LiAlH₄ / diethyl ether / 2 h / Heating 6: Et₃N / diethyl ether / 20 h / Ambient temperature

Reference： [1]Conti, Paola; Dallanoce, Clelia; De Amici, Marco; De Micheli, Carlo; Carrea, Giacomo; Zambianchi, Francesca [Tetrahedron Asymmetry, 1998, vol. 9, # 4, p. 657 - 665]

38
[ 2144-40-3 ]
Butyric acid (2R,5S)-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-2-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 44 percent / n-Bu₄NHSO₄, aq. NaOH / CH₂Cl₂ / 4 h / Ambient temperature 2: 85 percent / Et₃N / CH₂Cl₂ / 0 °C

Reference： [1]Conti, Paola; Dallanoce, Clelia; De Amici, Marco; De Micheli, Carlo; Carrea, Giacomo; Zambianchi, Francesca [Tetrahedron Asymmetry, 1998, vol. 9, # 4, p. 657 - 665]

39
[ 2144-40-3 ]
Butyric acid (2S,5R)-5-iodomethyl-tetrahydro-furan-2-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 44 percent / n-Bu₄NHSO₄, aq. NaOH / CH₂Cl₂ / 4 h / Ambient temperature 2: 85 percent / Et₃N / CH₂Cl₂ / 0 °C 3: 79 percent / NaI / butan-2-one / Heating

Reference： [1]Conti, Paola; Dallanoce, Clelia; De Amici, Marco; De Micheli, Carlo; Carrea, Giacomo; Zambianchi, Francesca [Tetrahedron Asymmetry, 1998, vol. 9, # 4, p. 657 - 665]

40
[ 2144-40-3 ]
Butyric acid (2S,5R)-5-iodomethyl-tetrahydro-furan-2-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 44 percent / n-Bu₄NHSO₄, aq. NaOH / CH₂Cl₂ / 4 h / Ambient temperature 2: 85 percent / Et₃N / CH₂Cl₂ / 0 °C 3: 79 percent / NaI / butan-2-one / Heating

Reference： [1]Conti, Paola; Dallanoce, Clelia; De Amici, Marco; De Micheli, Carlo; Carrea, Giacomo; Zambianchi, Francesca [Tetrahedron Asymmetry, 1998, vol. 9, # 4, p. 657 - 665]

41
[ 2144-40-3 ]
(+/-)-cis-2-(acetoxymethyl)-5-(hydroxymethyl)tetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 82 percent / pyridine / 24 h / Ambient temperature 2: 33 percent / acetic anhydride, pyridine / 24 h / Ambient temperature

Reference： [1]Naemura; Fukuda; Takahashi; Konishi; Hirose; Tobe [Tetrahedron Asymmetry, 1993, vol. 4, # 5, p. 911 - 918]

42
2,5-anhydro-4,6-di-O-benzoyl-2,3-didehydro-3-deoxyglucononitrile [ No CAS ]
[ 2144-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 2.) H₂ / 2.) Pd/C / 2.) MeOH, 1 h 2: 83 percent / HCl gas / dioxane; H₂O / 12 h / 60 °C 3: 76 percent / LiAlH₄ / tetrahydrofuran / Heating

Reference： [1]Jung, Michael E.; Trifunovich, Ivan D.; Sledeski, Adam W. [Heterocycles, 1993, vol. 35, # 1, p. 273 - 280]

43
β-2,5-anhydro-6-O-benzoyl-3,4-dideoxyglucononitrile [ No CAS ]
[ 2144-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 83 percent / HCl gas / dioxane; H₂O / 12 h / 60 °C 2: 76 percent / LiAlH₄ / tetrahydrofuran / Heating

Reference： [1]Jung, Michael E.; Trifunovich, Ivan D.; Sledeski, Adam W. [Heterocycles, 1993, vol. 35, # 1, p. 273 - 280]

44
[ 2144-40-3 ]
[ 119943-83-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: pyridine / diethyl ether 2: phosphate buffer / pig liver esterase / H₂O / 18 h / 0 °C 3: 1.) CrO₃ / 1.) acetone 4: sodium carbonate / H₂O / Ambient temperature 5: diethyl ether

Reference： [1]Naemura, Koichiro; Takahashi, Nobuo; Chikamatsu, Hiroaki [Chemistry Letters, 1988, # 10, p. 1717 - 1720]

45
[ 2144-40-3 ]
(2R,5S)-(-)-2-(acetoxymethyl)-5-(hydroxymethyl)tetrahydofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine / diethyl ether 2: phosphate buffer / pig liver esterase / H₂O / 18 h / 0 °C

Reference： [1]Naemura, Koichiro; Takahashi, Nobuo; Chikamatsu, Hiroaki [Chemistry Letters, 1988, # 10, p. 1717 - 1720]

46
[ 2144-40-3 ]
Isobutyric acid (2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine / diethyl ether 2: phosphate buffer / pig liver esterase / H₂O / 2.8 h / 0 °C

Reference： [1]Naemura, Koichiro; Takahashi, Nobuo; Chikamatsu, Hiroaki [Chemistry Letters, 1988, # 10, p. 1717 - 1720]

47
[ 2144-40-3 ]
[ 119873-57-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: pyridine / diethyl ether 2: phosphate buffer / pig liver esterase / H₂O / 18 h / 0 °C 3: 1.) CrO₃ / 1.) acetone

Reference： [1]Naemura, Koichiro; Takahashi, Nobuo; Chikamatsu, Hiroaki [Chemistry Letters, 1988, # 10, p. 1717 - 1720]

48
[ 2144-40-3 ]
[ 119873-59-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: pyridine / diethyl ether 2: phosphate buffer / pig liver esterase / H₂O / 2.8 h / 0 °C 3: 1.) CrO₃ / 1.) acetone

Reference： [1]Naemura, Koichiro; Takahashi, Nobuo; Chikamatsu, Hiroaki [Chemistry Letters, 1988, # 10, p. 1717 - 1720]

49
[ 2144-40-3 ]
[ 119943-82-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: pyridine / diethyl ether 2: phosphate buffer / pig liver esterase / H₂O / 18 h / 0 °C 3: 1.) CrO₃ / 1.) acetone 4: sodium carbonate / H₂O / Ambient temperature

Reference： [1]Naemura, Koichiro; Takahashi, Nobuo; Chikamatsu, Hiroaki [Chemistry Letters, 1988, # 10, p. 1717 - 1720]

50
[ 2144-40-3 ]
cis-5-azidomethyl-2-octadecylcarbamoyloxymethyltetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 23 percent / pyridine / 15 h / 60 °C 2: Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature 3: LiN₃ / dimethylformamide / 15 h / 70 °C

Reference： [1]Tsuri; Haga; Matsui; Kamata; Kakushi; Uchida [Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 1, p. 75 - 84]

51
[ 2144-40-3 ]
[ 140685-56-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 23 percent / pyridine / 15 h / 60 °C 2: Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

Reference： [1]Tsuri; Haga; Matsui; Kamata; Kakushi; Uchida [Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 1, p. 75 - 84]

52
[ 2144-40-3 ]
[ 140685-42-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 23 percent / pyridine / 15 h / 60 °C 2: Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature 3: LiN₃ / dimethylformamide / 15 h / 70 °C 4: 1.) PPh₃, 2.) H₂O / 1.) THF, RT, 63 h, 2.) THF, reflux, 1 h 5: 69 percent / Et₃N / CH₂Cl₂ / Ambient temperature

Reference： [1]Tsuri; Haga; Matsui; Kamata; Kakushi; Uchida [Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 1, p. 75 - 84]

53
[ 2144-40-3 ]
[ 140685-43-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 23 percent / pyridine / 15 h / 60 °C 2: Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature 3: LiN₃ / dimethylformamide / 15 h / 70 °C 4: 1.) PPh₃, 2.) H₂O / 1.) THF, RT, 63 h, 2.) THF, reflux, 1 h 5: 69 percent / Et₃N / CH₂Cl₂ / Ambient temperature 6: 94 percent / NaI / butan-2-one / 3 h / Heating

Reference： [1]Tsuri; Haga; Matsui; Kamata; Kakushi; Uchida [Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 1, p. 75 - 84]

54
[ 2144-40-3 ]
[ 140685-55-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 23 percent / pyridine / 15 h / 60 °C 2: Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature 3: LiN₃ / dimethylformamide / 15 h / 70 °C 4: 1.) PPh₃, 2.) H₂O / 1.) THF, RT, 63 h, 2.) THF, reflux, 1 h

Reference： [1]Tsuri; Haga; Matsui; Kamata; Kakushi; Uchida [Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 1, p. 75 - 84]

55
[ 2240-81-5 ]
[ 2144-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 91 percent / diethyl ether 2: 80 percent / LiAlH₄ / diethyl ether / 12 h / Heating

Reference： [1]Nakazaki, Masao; Naemura, Koichiro; Makimura, Masaru; Matsuda, Atsushi; Kawano, Takaaki; Ohta, Yoshihiro [Journal of Organic Chemistry, 1982, vol. 47, # 12, p. 2429 - 2435]

56
[ 2144-40-3 ]
[ 96479-19-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: CH₂Cl₂ / Ambient temperature 2: 75 percent / 4.75 h / Ambient temperature; lipase from Mucor javanicus (LMJ), 0.1 M pH 7 buffer; other enzymes 3: PCC, Mol_.sieves / CH₂Cl₂ / Ambient temperature 4: Br₂ / H₂O / Ambient temperature 5: K₂CO₃ / methanol / Ambient temperature

Reference： [1]Estermann; Prasad; Shapiro; Repic; Hardtmann; Bolsterli; Walkinshaw [Tetrahedron Letters, 1990, vol. 31, # 4, p. 445 - 448]

57
[ 2144-40-3 ]
[ 128365-69-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: CH₂Cl₂ / Ambient temperature 2: 75 percent / 4.75 h / Ambient temperature; lipase from Mucor javanicus (LMJ), 0.1 M pH 7 buffer; other enzymes 3: PCC, Mol_.sieves / CH₂Cl₂ / Ambient temperature

Reference： [1]Estermann; Prasad; Shapiro; Repic; Hardtmann; Bolsterli; Walkinshaw [Tetrahedron Letters, 1990, vol. 31, # 4, p. 445 - 448]

58
[ 2144-40-3 ]
Butyric acid (2S,5R)-5-hydroxymethyl-tetrahydro-furan-2-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: CH₂Cl₂ / Ambient temperature 2: 75 percent / 4.75 h / Ambient temperature; lipase from Mucor javanicus (LMJ), 0.1 M pH 7 buffer; other enzymes

Reference： [1]Estermann; Prasad; Shapiro; Repic; Hardtmann; Bolsterli; Walkinshaw [Tetrahedron Letters, 1990, vol. 31, # 4, p. 445 - 448]

59
[ 2144-40-3 ]
[ 128365-70-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: CH₂Cl₂ / Ambient temperature 2: 75 percent / 4.75 h / Ambient temperature; lipase from Mucor javanicus (LMJ), 0.1 M pH 7 buffer; other enzymes 3: PCC, Mol_.sieves / CH₂Cl₂ / Ambient temperature 4: Br₂ / H₂O / Ambient temperature

Reference： [1]Estermann; Prasad; Shapiro; Repic; Hardtmann; Bolsterli; Walkinshaw [Tetrahedron Letters, 1990, vol. 31, # 4, p. 445 - 448]

60
[ 2144-40-3 ]
[ 280-13-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine 2: methanol. NH₃ / 160 °C / Erhitzen des Reaktionsprodukts mit wss. Ba(OH)2

Reference： [1]Newth; Wiggins [Journal of the Chemical Society, 1948, p. 155,157]

61
[ 2144-40-3 ]
3-ethyl-8-oxa-3-aza-bicyclo[3.2.1]octane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine; thionyl chloride 2: 165 °C

Reference： [1]Cope; Anderson [Journal of the American Chemical Society, 1955, vol. 77, p. 995,997]

62
[ 2144-40-3 ]
[ 99969-71-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine 2: THF / 135 - 140 °C

Reference： [1]Cope; Baxter [Journal of the American Chemical Society, 1955, vol. 77, p. 393,395]

63
[ 2144-40-3 ]
1-(8-oxa-3-aza-bicyclo[3.2.1]oct-3-yl)-propan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine 2: THF / 135 - 140 °C

Reference： [1]Cope; Baxter [Journal of the American Chemical Society, 1955, vol. 77, p. 393,395]

64
[ 2144-40-3 ]
3-nitroso-8-oxa-3-aza-bicyclo[3.2.1]octane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: pyridine 2: methanol. NH₃ / 160 °C / Erhitzen des Reaktionsprodukts mit wss. Ba(OH)2 3: aqueous KNO₂; acetic acid

Reference： [1]Newth; Wiggins [Journal of the Chemical Society, 1948, p. 155,157]

65
[ 2144-40-3 ]
3-acetyl-8-oxa-3-aza-bicyclo[3.2.1]octane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: pyridine 2: methanol. NH₃ / 160 °C / Erhitzen des Reaktionsprodukts mit wss. Ba(OH)2 3: sodium acetate

Reference： [1]Newth; Wiggins [Journal of the Chemical Society, 1948, p. 155,157]

66
[ 2144-40-3 ]
<i>cis</i>-2,5-bis-ethoxymethyl-tetrahydro-furan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine 2: aq. NaOH solution

Reference： [1]Newth; Wiggins [Journal of the Chemical Society, 1948, p. 155,157]

67
[ 2144-40-3 ]
[ 97301-22-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine; thionyl chloride 2: 165 °C

Reference： [1]Cope; Anderson [Journal of the American Chemical Society, 1955, vol. 77, p. 995,997] Newth; Wiggins [Journal of the Chemical Society, 1948, p. 155,157]

68
[ 2144-40-3 ]
[ 106479-04-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: pyridine; thionyl chloride 2: 165 °C

Reference： [1]Cope; Anderson [Journal of the American Chemical Society, 1955, vol. 77, p. 995,997] Newth; Wiggins [Journal of the Chemical Society, 1948, p. 155,157]

69
[ 4282-32-0 ]
[ 2144-40-3 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 393,395

70
[ 20221-46-9 ]
[ 2144-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: water / 210 °C / Erhitzen des Reaktionsprodukts mit Aethanol, Toluol und wenig Schwefelsaeure 2: lithium alanate; tetrahydrofuran

Reference： [1]Gryszkiewicz-Trochimowski et al. [Bulletin de la Societe Chimique de France, 1958, p. 610,615]

71
[ 2144-40-3 ]
[ 67-64-1 ]
[ 108-95-2 ]

Yield	Reaction Conditions	Operation in experiment
730 mg (25%)	With NaH; sodium chloride In tetrahydrofuran; dichloromethane; chloroform; mineral oil	Preparation of Compound 16 Preparation of Compound 16 To a refluxing suspension of 3.0 g (62.5 mmol) of NaH (50% in mineral oil) in 400 mL of THF under Ar was added to a solution of 3.0 g (4.5 mmol) of 15 and 610 mg (4.6 mmol) of cis-2,5-bishydroxymethyltetrahydrofuran in 800 mL of THF over 8 h. The mixture was refluxed for an additional 16 h, cooled to 25° C., excess NaH decomposed with CH3 OH, and the solvent was evaporated at 30°/30 mm. The residue was dissolved in 500 mL portions of CHCl3 and 10% NaCl, acidified to pH~3, and the organic layer was separated, dried, concentrated to 15 mL, and added to a silica gel column (150 g) made up in CH2 Cl2. Elution of the column with CH2 Cl2 (1 L) and 19:1 and 9:1 CH2 - acetone (2 L of each) gave traces of unidentified material. Further elution of the column with 4:1 and 7:3 CH2 Cl2 -acetone mixtures (2 L of each) gave 730 mg (25%) of 16 as a white foam. The mass spectrum (70 eV) gave the expected molecular ion at m/e 638. The 1 H NMR spectrum (200 MHz, CDCl3) gave absorptions at δ 0.76 (t, inner OCH2 CH3, 3H), 0.98-1.18 (m, outer OCH2 CH3, 6H), 1.53- 2.41 (m, ArCH3, CH2 CH2, 10H), 3.38-4.65 (m, OCH2, CH2 CHO, 16H) and 7.03-7.42 (m, ArH, 10H).

Reference： [1]Current Patent Assignee: BAYER AG; UNIVERSITY OF CALIFORNIA - US5177221, 1993, A

72
[ 2144-40-3 ]
[ 1643-19-2 ]
[ 112-89-0 ]
cis-2-[(octadecylaminocarbonyl)oxy]methyl-5-hydroxymethyl tetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile	1 Cis-2-[(octadecylaminocarbonyl)oxy]methyl-5-hydroxymethyl tetrahydrofuran STR11 EXAMPLE 1 Cis-2-[(octadecylaminocarbonyl)oxy]methyl-5-hydroxymethyl tetrahydrofuran STR11 A suspension of 2.64 g (20 mmol) of cis-2,5-bis(hydroxymethyl)tetrahydrofuran, 7.99 g (24 mmol) of octadecyl bromide, 2.43 g (30 mmol) of potassium cyanate and 0.966 g (3 mmol) of tetrabutyl ammonium bromide in 100 ml of dry acetonitrile was refluxed, with stirring, at 100° C. for 20 hours. The resultant mixture was then diluted with hot methylene chloride, filtered and the filtrate concentrated in vacuo. The crude product was then purified by flash silica gel chromatography employing successive mixtures of petroleum ether and ethyl acetate in ratios of 4:1, 2.33:1 and 1:1 as the eluent to yield the title compound as a solid, m.p. 79°-80° C.

Reference： [1]Current Patent Assignee: Sandoz (in: Novartis); NOVARTIS AG - US4868319, 1989, A

73
[ 2144-40-3 ]
[ 108-24-7 ]
(tetrahydrofüran-2,5-diyl)dimethanol [ No CAS ]
(2R,5S)-(-)-2-(acetoxymethyl)-5-(hydroxymethyl)tetrahydofuran [ No CAS ]
(2S,5R)-(+)-2-(acetoxymethyl)-5-(hydroxymethyl)tetrahydofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39 % ee	With C₄₂H₆₀N₆O₇; N-ethyl-N,N-diisopropylamine In toluene at 0℃; for 5h;

Reference： [1]Mueller, Christian E.; Zell, Daniela; Hrdina, Radim; Wende, Raffael C.; Wanka, Lukas; Schuler, Soeren M. M.; Schreiner, Peter R. [Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8465 - 8484]

74
[ 2144-40-3 ]
[ 108-24-7 ]
(+/-)-cis-2-(acetoxymethyl)-5-(hydroxymethyl)tetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With dmap In dichloromethane at 25℃;

Reference： [1]Mueller, Christian E.; Zell, Daniela; Hrdina, Radim; Wende, Raffael C.; Wanka, Lukas; Schuler, Soeren M. M.; Schreiner, Peter R. [Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8465 - 8484]

75
[ 3397-62-4 ]
[ 2144-40-3 ]
4,6-diamino-2-[(2'RS,5'SR)-5'-(hydroxymethyl)tetrahydrofuran-2'-yl]methoxy}-1,3,5-triazine dihydrochloride [ No CAS ]
(2R,5S)-2,5-bis[(4',6'-diamino-1',3',5'-triazin-2'-yl)oxymethyl]tetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 42% 2: 14%	In N,N-dimethyl-formamide at 100℃; for 48h;

Reference： [1]Fernndez-Cureses, Gloria; De Castro, Sonia; Jimeno, Mara-Luisa; Balzarini, Jan; Camarasa, Mara-Jos [ChemMedChem, 2015, vol. 10, # 2, p. 321 - 335]

76
[ 2144-40-3 ]
(1R,5S)-8-oxa-3-azabicyclo[3.2.1]octane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tert-Amyl alcohol at 150℃; for 40h; Inert atmosphere; Autoclave;	2 Example 2: Homogeneously catalytic process using Ru-based Catalyst (HI) In a nitrogen-purged sealed autoclave (25 ml), 2,5- bis(hydroxymethyl)tetrahydrofuran (264 mg, 2.0 mmol), Xantphos (3 mol%) and [Ru(CO)CIH(PPh3)3] (3mol%) were dissolved in 2 ml of tert-amyl alcohol and then charged with 5 bar NH3. The mixture was heated at 1500C for 40 hours. The thus obtained product was then analysed by NMR and CC using biphenyl as internal standard. The bicyclic product (I, R = H) was obtained in 93% yield.

Reference： [1]Current Patent Assignee: SOLVAY; CHINESE ACADEMY OF SCIENCES - WO2015/109451, 2015, A1 Location in patent: Paragraph 0080

77
[ 2144-40-3 ]
[ 100-46-9 ]
3-benzyl-8-oxa-3-azabicyclo[3.2.1]octane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With C₅H₁₄IrN₃⁽²⁺⁾*2I^(1-) In water at 120℃; for 20h; Inert atmosphere; Sealed tube;	1 Example 1: Homogeneously catalytic process using Ir-based Catalyst (HI) In a nitrogen-purged sealed caroulsel tube, 2,5- bis(hydroxymethyl)tetrahydrofuran (132 mg, 1.Ommol) and benzylamine(268 mg, 2.5 mmol.) in 0.5 ml of water containing 3.0 mol% of [Cp*lr(NH3)3][l]2 catalyst were heated at 120°C for 20 hours. The reaction mixture was then cooled and extracted with ethyl acetate (2m1 x 3 times). The thus obtained product was then analysed by NMR and CC using biphenyl as the internal standard. The bicyclic product (I, R = benzyl) was obtained in 94% yield.

Reference： [1]Current Patent Assignee: SOLVAY; CHINESE ACADEMY OF SCIENCES - WO2015/109451, 2015, A1 Location in patent: Paragraph 0079

78
1,5-hexadiene diepoxide [ No CAS ]
tetrahydrofuran-2,5-dimethanol [ No CAS ]
[ 2144-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In water at 20℃; for 16h; Overall yield = 70 %;	(±)-((2S,5S)-tetrahydrofuran-2,5-diyl) dimethanol 6a,((2R,5R)-tetrahydrofuran-2,5-diyl) dimethanol 6b: and((2R,5S)-tetrahydrofuran-2,5-diyl) dimethanol 6c from 1,5-hexadiene 17 through the 1,5-diepoxide 18: 3-Chloroperoxybenzoicacid (57-60%, 48.6 g, 281 mmol) was addedin five portions to a mechanically-stirred solution of 1,5-hexadiene 17 (4.84 g, 59 mmol) in CH2Cl2 (150 mL) whilecooling (0°C). The reaction mixture was allowed to warm toroom temperature then stirring was continued (16h). Saturatedaqueous sodium bicarbonate (100 mL) was then addedto the reaction mixture while stirring followed by separationof the organic layer and washing with 1M aqueous KOH (7 x50 mL). The organic layer was then dried over anhydrousMgSO4, filtered and concentrated to provide the racemic/meso 1, 5-diepoxides 18 (6.8 g, >99%). A mixture ofaqueous NaOH (18 mL, 0.1M) and the diepoxide 18 (1.0 g,8.7 mmol) was stirred at room temperature (16 h). Water wasthen removed and the oily residue was flushed through asilica gel column giving the mixture of oily (2S,5S)-6a,(2R,5R)-6b and (2S,5R)-6c diols (0.8 g, 70%). The mixturewas then submitted to gravity-column chromatography(CHCl3/tert-butanol, 7/3) which separated the more mobile(2S,5R)-6c from the racemic mixture of 6a/6b. Acetylation(Ac2O/pyridine) of a portion of the 6a/6b/6c mixture followedby flash chromatography gave a mixture of the threecorresponding stereoisomeric diacetates. The diacetates weresubmitted to chiral HPLC (ChiracelOJ, 4.6 x 250 mm, 10;mobile phase 80% hexane/20% ethanol; 0.7 mL/min, 22°C)and indicated that the ratio of racemic: meso diacetates was54:46.

Reference： [1]Qayed, Wesam S.; Luzzio, Frederick A. [Letters in Organic Chemistry, 2015, vol. 12, # 9, p. 622 - 630]

79
[ 67-47-0 ]
[ 1883-75-6 ]
[ 2144-40-3 ]
trans-2,5-bis-hydroxymethyltetrahydrofurane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrogen In ethanol at 120℃; for 3h; Autoclave;	6 EXAMPLE 6: HMF reduction to FDM EXAMPLE 6: HMF reduction to FDMCopper zinc nanopowder and some commercial catalysts were also tested the hydrogenation of HMF at mild temperature for the achievement of useful diol building blocks (suppliers are indicated in table 6). Table 7. Composition details (and suppliers) of the commercial catalysts used.The vessel was pressurized with 70 bar H2 and subsequently heated to 120 C for 3 hours. In the adopted experimental conditions, all commercial catalysts showed good to excellent activity in the hydrogenation of HMF to FDM (2,5-furandimethanol) and THFDM (2,5-tetrahydrofurandimethanol), which account together for a combined selectivity of >80% (see Scheme 3).Scheme 3. Commercial compositions, such as catalyst D and catalyst G, both based on copper and nickel supported on S1O2 and Si02 Zr02, respectively, showed good selectivity to FDM (Table 8, entry 1 and 2) but no complete conversion of HMF, especially with catalyst G, which is characterized by a lower content of Cu and Ni than catalyst D. Ni Raney alloy showed complete conversion of HMF and high selectivity to THFDM (94%, table 8, entry 3), while Ni supported on ceria and zirconia (table 8, entry 4) led to an approximately equimolar mixture of FDM and THFDM. The strong interaction between nickel and the support might cause a reduced hydrogenation activity. Also the simultaneous presence of copper and nickel centres may attenuate the hydrogenation activity of nickel, which is very active in the reduction of C=C bonds (Table 8, entry 1 and 2 vs. entry 3).Interestingly, Cu-Zn alloy showed quantitative conversion of HMF and excellent selectivity to FDM (94%, table 8, entry 5), with no ring- hydrogenation. With the exception of Pt/C, which also selectively reduced HMF to FDM (table 8, entry 6), other hydrogenation catalysts based on noble metals preferably gave THFDM or a mixture of FDM and THFDM. Interestingly, Pd/A Oe and Pd/C showed high selectivity to THFDM by hydrogenation of both C=0 and C=C bonds (table 8, entry 7 and 8).
1%	With palladium/alumina; hydrogen In ethanol at 120℃; for 3h; Autoclave;	6 EXAMPLE 6: HMF reduction to FDM EXAMPLE 6: HMF reduction to FDMCopper zinc nanopowder and some commercial catalysts were also tested the hydrogenation of HMF at mild temperature for the achievement of useful diol building blocks (suppliers are indicated in table 6). Table 7. Composition details (and suppliers) of the commercial catalysts used.The vessel was pressurized with 70 bar H2 and subsequently heated to 120 C for 3 hours. In the adopted experimental conditions, all commercial catalysts showed good to excellent activity in the hydrogenation of HMF to FDM (2,5-furandimethanol) and THFDM (2,5-tetrahydrofurandimethanol), which account together for a combined selectivity of >80% (see Scheme 3).Scheme 3. Commercial compositions, such as catalyst D and catalyst G, both based on copper and nickel supported on S1O2 and Si02 Zr02, respectively, showed good selectivity to FDM (Table 8, entry 1 and 2) but no complete conversion of HMF, especially with catalyst G, which is characterized by a lower content of Cu and Ni than catalyst D. Ni Raney alloy showed complete conversion of HMF and high selectivity to THFDM (94%, table 8, entry 3), while Ni supported on ceria and zirconia (table 8, entry 4) led to an approximately equimolar mixture of FDM and THFDM. The strong interaction between nickel and the support might cause a reduced hydrogenation activity. Also the simultaneous presence of copper and nickel centres may attenuate the hydrogenation activity of nickel, which is very active in the reduction of C=C bonds (Table 8, entry 1 and 2 vs. entry 3).Interestingly, Cu-Zn alloy showed quantitative conversion of HMF and excellent selectivity to FDM (94%, table 8, entry 5), with no ring- hydrogenation. With the exception of Pt/C, which also selectively reduced HMF to FDM (table 8, entry 6), other hydrogenation catalysts based on noble metals preferably gave THFDM or a mixture of FDM and THFDM. Interestingly, Pd/A Oe and Pd/C showed high selectivity to THFDM by hydrogenation of both C=0 and C=C bonds (table 8, entry 7 and 8).

Reference： [1]Current Patent Assignee: UNIVERSITY OF GRONINGEN - WO2016/43589, 2016, A1 Location in patent: Page/Page column 25; 26; 27
[2]Current Patent Assignee: UNIVERSITY OF GRONINGEN - WO2016/43589, 2016, A1 Location in patent: Page/Page column 25; 26; 27

80
1,6-anhydro-3,4-dideoxy-β-D-threo/erythro-hexopyranose [ No CAS ]
[ 6126-49-4 ]
[ 2144-40-3 ]
[ 81370-88-9 ]
(6S)-6-(hydroxymethyl)dihydro-2H-pyran-3(4H)-one [ No CAS ]
tetrahydropyran-2-methanol-5-hydroxyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 42.5 %Chromat. 2: 15.4 %Chromat. 3: 17.1 %Chromat. 4: 20.1 %Chromat. 5: 3.4 %Chromat.	With hydrogen In tetrahydrofuran at 150℃; for 3h;

Reference： [1]Krishna, Siddarth H.; McClelland, Daniel J.; Rashke, Quinn A.; Dumesic, James A.; Huber, George W. [Green Chemistry, 2017, vol. 19, # 5, p. 1278 - 1285]

81
[ 2144-40-3 ]
((2R,5S)-5-(iodomethyl)tetrahydrofuran-2-yl)methanol [ No CAS ]
((2R,5S)-5-((((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)methoxy)methyl)tetrahydrofuran-2-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	Stage #1: cis-2,5-bis(hydroxymethyl)tetrahydrofuran With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Cooling; Stage #2: ((2R,5S)-5-(iodomethyl)tetrahydrofuran-2-yl)methanol In tetrahydrofuran; mineral oil	5 Example 5. Preparation of ((2R,5S)-5-((((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2- Experimental: A flame-dried, 100 mL boiling flask was charged with 1 g of ((2R,5S)- tetrahydrofuran-2,5-diyl)dimethanol (A, 7.57 mmol)) and 25 mL of anhydrous THF. The flask was immersed in a saturated brine/ice bath (~ -10°C) and 302 mg of sodium hydride (60 wt.% in mineral oil, 7.57 mmol) added in 5 portions (-60 mg) over 15 min. After complete addition, the resultant suspension was stirred for 15 min, furnishing an intense green color. A septum was then placed over the neck of the flask, and 1.86 g of ((2R, 5S)-5-(iodomethyl)tetrahydrofuran-2-yl)methanol (B, 7.57 mmol) dissolved in 10 mL of THF was added dropwise via syringe over 15 min. After addition, the brine/ice bath was removed and reaction stirred overnight. After this time, solids were filtered and filtrate poured over a pre-fabricated silica gel column, where flash chromatography with a gradient hexanes- >hexanes/ethyl acetate furnished 1.08 g of the title compound as a colorless oil (58%). The structure was of the product was validated by NMR. NMR (400 MHz, CDC13) δ (ppm) 5.00 (broad s, 2H), 4.02 (m, 2H), 3.82 (m, 2H), 3.66-3.61 (m, 4H), 3.47-3.51 (m, 4H), 2.02 (m, 4H), 1.74 (m, 4H). 13C NMR (100 MHz, CDC13) δ (ppm) 88.8, 85.4, 77.2, 65.1, 30.8, 29.4.

Reference： [1]Current Patent Assignee: ARCHER-DANIELS-MIDLAND CO - WO2017/222532, 2017, A1 Location in patent: Paragraph 0041-0042

82
[ 67-47-0 ]
[ 7326-46-7 ]
[ 6126-49-4 ]
[ 100-72-1 ]
[ 2144-40-3 ]
[ 110-13-4 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium on activated charcoal; water; hydrogen at 170℃; for 2h; Autoclave;

Reference： [1]Hu, Xun; Westerhof, Roel J. M.; Wu, Liping; Dong, Dehua; Li, Chun-Zhu [Green Chemistry, 2015, vol. 17, # 1, p. 219 - 224]

83
[ 67-56-1 ]
[ 67-47-0 ]
[ 97-99-4 ]
[ 6126-49-4 ]
[ 100-72-1 ]
[ 2144-40-3 ]
[ 106-69-4 ]
[ 107-31-3 ]
trans-tetrahydro-(5-(methoxymethyl)furan-2-yl)methanol [ No CAS ]
cis-tetrahydro-(5-(methoxymethyl)furan-2-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium on activated charcoal; hydrogen at 170℃; for 2h; Autoclave;

Reference： [1]Hu, Xun; Westerhof, Roel J. M.; Wu, Liping; Dong, Dehua; Li, Chun-Zhu [Green Chemistry, 2015, vol. 17, # 1, p. 219 - 224]

84
[ 2144-40-3 ]
C₂₅H₂₉N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 6.5 h / 0 - 25 °C 2.1: tetrahydrofuran / 110 °C 3.1: 1-methyl-pyrrolidin-2-one / 15 h / 170 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 6.5 h / 0 - 25 °C 2.1: tetrahydrofuran / 110 °C 3.1: 1-methyl-pyrrolidin-2-one / 15 h / 190 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: CHENGDU EASTON BIOPHARMACEUTICALS - CN108623541, 2018, A
[2]Current Patent Assignee: CHENGDU EASTON BIOPHARMACEUTICALS - CN108623541, 2018, A

85
[ 2144-40-3 ]
2-[(2R,5S)-5-[[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]methyl]tetrahydrofuran-2-yl]methoxy}acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 6.5 h / 0 - 25 °C 2.1: tetrahydrofuran / 110 °C 3.1: 1-methyl-pyrrolidin-2-one / 15 h / 170 °C / Inert atmosphere 4.1: potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 12 h / 10 - 25 °C 5.1: lithium hydroxide / methanol / 2 h / 10 - 25 °C 5.2: pH 4-5
	Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 6.5 h / 0 - 25 °C 2.1: tetrahydrofuran / 110 °C 3.1: 1-methyl-pyrrolidin-2-one / 15 h / 190 °C / Inert atmosphere 4.1: potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 12 h / 10 - 25 °C 5.1: lithium hydroxide / methanol / 2 h / 10 - 25 °C 5.2: pH 4-5
	Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 6.5 h / 0 - 25 °C 2.1: tetrahydrofuran / 110 °C 3.1: 1-methyl-pyrrolidin-2-one / 15 h / 170 °C / Inert atmosphere 4.1: potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / N,N-dimethyl-formamide / 12 h / 10 - 25 °C 5.1: lithium hydroxide / methanol / 2 h / 10 - 25 °C 5.2: pH 4-5

Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 6.5 h / 0 - 25 °C 2.1: tetrahydrofuran / 110 °C 3.1: 1-methyl-pyrrolidin-2-one / 15 h / 190 °C / Inert atmosphere 4.1: potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / N,N-dimethyl-formamide / 12 h / 10 - 25 °C 5.1: lithium hydroxide / methanol / 2 h / 10 - 25 °C 5.2: pH 4-5

Reference： [1]Current Patent Assignee: CHENGDU EASTON BIOPHARMACEUTICALS - CN108623541, 2018, A
[2]Current Patent Assignee: CHENGDU EASTON BIOPHARMACEUTICALS - CN108623541, 2018, A
[3]Current Patent Assignee: CHENGDU EASTON BIOPHARMACEUTICALS - CN108623541, 2018, A
[4]Current Patent Assignee: CHENGDU EASTON BIOPHARMACEUTICALS - CN108623541, 2018, A

86
[ 2144-40-3 ]
2-[(2R,5S)-5-[[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]methyl]tetrahydrofuran-2-yl]methoxy}acetic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 6.5 h / 0 - 25 °C 2.1: tetrahydrofuran / 110 °C 3.1: 1-methyl-pyrrolidin-2-one / 15 h / 170 °C / Inert atmosphere 4.1: potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 12 h / 10 - 25 °C
	Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 6.5 h / 0 - 25 °C 2.1: tetrahydrofuran / 110 °C 3.1: 1-methyl-pyrrolidin-2-one / 15 h / 190 °C / Inert atmosphere 4.1: potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 12 h / 10 - 25 °C
	Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 6.5 h / 0 - 25 °C 2.1: tetrahydrofuran / 110 °C 3.1: 1-methyl-pyrrolidin-2-one / 15 h / 170 °C / Inert atmosphere 4.1: potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / N,N-dimethyl-formamide / 12 h / 10 - 25 °C

Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 6.5 h / 0 - 25 °C 2.1: tetrahydrofuran / 110 °C 3.1: 1-methyl-pyrrolidin-2-one / 15 h / 190 °C / Inert atmosphere 4.1: potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / N,N-dimethyl-formamide / 12 h / 10 - 25 °C

Reference： [1]Current Patent Assignee: CHENGDU EASTON BIOPHARMACEUTICALS - CN108623541, 2018, A
[2]Current Patent Assignee: CHENGDU EASTON BIOPHARMACEUTICALS - CN108623541, 2018, A
[3]Current Patent Assignee: CHENGDU EASTON BIOPHARMACEUTICALS - CN108623541, 2018, A
[4]Current Patent Assignee: CHENGDU EASTON BIOPHARMACEUTICALS - CN108623541, 2018, A

87
[ 2144-40-3 ]
C₉H₁₉NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 6.5 h / 0 - 25 °C 2.1: tetrahydrofuran / 110 °C

Reference： [1]Current Patent Assignee: CHENGDU EASTON BIOPHARMACEUTICALS - CN108623541, 2018, A

88
[ 2144-40-3 ]
[ 98-59-9 ]
C₁₃H₁₈O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: cis-2,5-bis(hydroxymethyl)tetrahydrofuran With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran at 0 - 25℃; for 6.5h;	3 Under the ice bath,Cis 2,5-dimethyloltetrahydrofuran(26.4g, 0.2mol) dissolved in 500mL tetrahydrofuranNaH (8.8 g, 0.22 mol) was added, stirred at 0 ° C for 30 min, then p-toluenesulfonyl chloride (41.8 g, 0.22 mol).After continuing to react at 0 ° C for 30 min, the temperature was naturally raised to room temperature, and the reaction was carried out for 6 h, and water (100 mL) and ethyl acetate (200 mL) were added for extraction.The organic phase is concentrated, concentrated under reduced pressure, and the crude product is purified by chromatography on silica gel column.The cis-(5-(hydroxymethyl)tetrahydrofuran-2-yl)p-toluenesulfonate methyl group was collected under reduced pressure.After directly adding 33 mL of isopropylamine, the tube was heated to 110 ° C to carry out a reaction, and the reaction was overnight.After cooling to room temperature, decompress isopropylamine at low temperature, then purified by chromatography on silica gel column, collected under reduced pressure, and dried in vacuo to give 27.8 g.Yellow oily cis-5-(isopropylaminomethyl)tetrahydrofuran-2-yl)methanol, yield: 80.2%

Reference： [1]Current Patent Assignee: CHENGDU EASTON BIOPHARMACEUTICALS - CN108623541, 2018, A Location in patent: Paragraph 0045-0047; 0066-0068; 0085-0087; 0104-0106; 0123

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	2144-40-3	MDL No. :	MFCD07369849
Formula :	C₆H₁₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YCZZQSFWHFBKMU-OLQVQODUSA-N
M.W :	132.16	Pubchem ID :	12886254
Synonyms :

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

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

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 2144-40-3 ] {[proInfo.proName]}

Quality Control of [ 2144-40-3 ]

Related Doc. of [ 2144-40-3 ]

Product Details of [ 2144-40-3 ]

Safety of [ 2144-40-3 ]

Application In Synthesis of [ 2144-40-3 ]

[ 2144-40-3 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 2144-40-3 ]

Alcohols

Related Parent Nucleus of
[ 2144-40-3 ]

Tetrahydrofurans

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 2144-40-3 ] {[proInfo.proName]}

Quality Control of [ 2144-40-3 ]

Related Doc. of [ 2144-40-3 ]

Product Details of [ 2144-40-3 ]

Safety of [ 2144-40-3 ]

Application In Synthesis of [ 2144-40-3 ]

[ 2144-40-3 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 2144-40-3 ]

Alcohols

Related Parent Nucleus of [ 2144-40-3 ]

Tetrahydrofurans

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 2144-40-3 ]

Related Parent Nucleus of
[ 2144-40-3 ]