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[ CAS No. 406913-93-7 ]

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2D
Chemical Structure| 406913-93-7
Chemical Structure| 406913-93-7
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Product Details of [ 406913-93-7 ]

CAS No. :406913-93-7MDL No. :MFCD16652371
Formula : C5H10O3 Boiling Point : 208.2±15.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :118.13Pubchem ID :44429359
Synonyms :

Computed Properties of [ 406913-93-7 ]

TPSA : 38.7 H-Bond Acceptor Count : 3
XLogP3 : -0.9 H-Bond Donor Count : 1
SP3 : 1.00 Rotatable Bond Count : 1

Safety of [ 406913-93-7 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 406913-93-7 ]

  • Upstream synthesis route of [ 406913-93-7 ]
  • Downstream synthetic route of [ 406913-93-7 ]

[ 406913-93-7 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 917882-63-4 ]
  • [ 406913-93-7 ]
YieldReaction ConditionsOperation in experiment
89% With palladium 10% on activated carbon; hydrogen In ethanol for 18 h; To a so[ution of Intermediate 83 (1 .25 g, 4.74 mmo[) in ethano[ (20 mL) was added pa[[adium, 10 percent on carbon (192 mg) and the reaction mixture stirred under an atmosphere of hydrogen for 18 h. The reaction mixture was fi[tered through a p[ugof Ce[ite®, washing with EtOAc, and concentrated under reduced pressure toafford 630 mg (89percent yie[d) of the tit[e compound as pa[e ye[[ow oi[.1H NMR (500 MHz, Ch[oroform-d): 6 [ppm] 3.85 - 3.67 (m, 5H), 3.66 - 3.57 (m, 2H),3.55 (dd, J = 11.7, 5.9 Hz, 1H), 3.46 (dd, J = 11.1, 10.0 Hz, 1H), 1.75 (5, 1H).
Reference: [1] Patent: WO2016/91776, 2016, A1, . Location in patent: Page/Page column 233
[2] Patent: US2006/293358, 2006, A1, . Location in patent: Page/Page column 50
[3] Patent: US2009/182002, 2009, A1, . Location in patent: Page/Page column 15
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 12, p. 4092 - 4108
  • 2
  • [ 934346-80-2 ]
  • [ 406913-93-7 ]
YieldReaction ConditionsOperation in experiment
20.8% With sodium hydroxide In tetrahydrofuran; water at 90℃; for 24 h; 2J (11.1 g, 81.3 mmol) was dissolved in 50 mL of THF. Sodium hydroxide (16.3 g, 406 mmol) in 50 mL of water was added and the reaction was heated in a 90 0C oil bath for one day. Despite the TLC showing the reaction to be only half completed the product was extracted from the aqueous layer with ethyl acetate/THF, dichloromethane, n-butanol. The first two extractions contained product and the starting material, which was later purified by flash <n="157"/>column (ethyl acetate/hexane 30/70). The latter extractions contained pure (S)-(1, 4-dioxan-2- yl)methanol (2K, 1.98 g, 20.8 percent yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.47 (t, 7=9.98 Hz, 1 H) 3.51 - 3.67 (m, 3 H) 3.67 - 3.87 (m, 5 H).
Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 7, p. 2667 - 2679
[2] Patent: WO2009/97578, 2009, A1, . Location in patent: Page/Page column 155-156
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 13, p. 3207 - 3211
  • 3
  • [ 27905-76-6 ]
  • [ 406913-93-7 ]
YieldReaction ConditionsOperation in experiment
30% With sodium hydroxide In water at 20 - 90℃; for 5 h; The product from step 1 (16.06 g, 92.81 mmol) and 1M NaOH (185 mL, 185 mmol) were mixed and the biphasic mixture stirred at RT. After 2.5 h the reaction mixture was heated to 90° C. degrees for 2.5 h then allowed to cool to RT and evaporated. The remaining slurry was washed with DCM/MeOH (95:5) three times, filtered and the filtrate was evaporated. The remaining 9.5 g of oil was purified by SiO2 chromatography (400 g SiO2) eluting with a MeOH/DCM gradient (0-4percent MeOH over 40 min) to afford a 30percent yield of [1,4]dioxan-2-yl-methanol (114a).
Reference: [1] Patent: US2008/249087, 2008, A1, . Location in patent: Page/Page column 35
  • 4
  • [ 51594-55-9 ]
  • [ 107-07-3 ]
  • [ 406913-93-7 ]
YieldReaction ConditionsOperation in experiment
23 g
Stage #1: With boron trifluoride diethyl etherate In toluene at 30 - 38℃; for 0.333333 h;
Stage #2: With sodium hydroxide In water; toluene at 16 - 20℃; for 1 h;
A mixture of (R)-2-(chloromethyl)oxirane (55, 109 mL, 1.62 mol) and BF3.OEt2 (3.4 mL, 0.027 mol) in toluene (200 mL) was heated to an internal temperature of 30° C. and 2-choloroethanol (49 g, 0.53 mol) was added dropwise at a rate sufficient to main the reaction temperature at 36-38° C. The resulting mixture was aged at 36° C. for 20 min. The mixture was cooled to 16° C. and aqueous NaOH (250 mL, 23percent) was added with vigorous stirring over 1 h, maintaining the reaction temperature below 20° C. The mixture was aged for 1 h at rt. The two layers were separated, and the aqueous phase was extracted with toluene (130 mL). The combined organic layers were washed with water (100 mL), the resulting organic layer was distilled to low volume, monitoring the distillate for loss of product to give the final intermediate 56 (23 g).1H-NMR: (CDCl3): δ 3.33-3.84 (m, 9H).
Reference: [1] Patent: US2014/57927, 2014, A1, . Location in patent: Paragraph 0294; 0295
  • 5
  • [ 861852-08-6 ]
  • [ 406913-93-7 ]
Reference: [1] Patent: WO2010/68863, 2010, A2, . Location in patent: Page/Page column 70
  • 6
  • [ 934346-53-9 ]
  • [ 406913-93-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 7, p. 2667 - 2679
[2] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 13, p. 3207 - 3211
  • 7
  • [ 406913-89-1 ]
  • [ 406913-93-7 ]
Reference: [1] Enantiomer, 2001, vol. 6, # 5, p. 267 - 273
  • 8
  • [ 29908-11-0 ]
  • [ 406913-93-7 ]
Reference: [1] Enantiomer, 2001, vol. 6, # 5, p. 267 - 273
  • 9
  • [ 18371-74-9 ]
  • [ 406913-93-7 ]
Reference: [1] Enantiomer, 2001, vol. 6, # 5, p. 267 - 273
  • 10
  • [ 406913-84-6 ]
  • [ 406913-93-7 ]
Reference: [1] Enantiomer, 2001, vol. 6, # 5, p. 267 - 273
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