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Chemical Structure| 22323-82-6
Chemical Structure| 22323-82-6
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Product Details of [ 22323-82-6 ]

CAS No. :22323-82-6 MDL No. :MFCD00063239
Formula : C6H12O3 Boiling Point : -
Linear Structure Formula :- InChI Key :RNVYQYLELCKWAN-YFKPBYRVSA-N
M.W : 132.16 Pubchem ID :736057
Synonyms :
S-(+)-2,3-O-Isopropylideneglycerol

Calculated chemistry of [ 22323-82-6 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 32.21
TPSA : 38.69 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.87
Log Po/w (XLOGP3) : -0.2
Log Po/w (WLOGP) : 0.13
Log Po/w (MLOGP) : -0.26
Log Po/w (SILICOS-IT) : 0.84
Consensus Log Po/w : 0.48

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.47
Solubility : 45.1 mg/ml ; 0.341 mol/l
Class : Very soluble
Log S (Ali) : -0.16
Solubility : 92.2 mg/ml ; 0.698 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.52
Solubility : 40.1 mg/ml ; 0.303 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.09

Safety of [ 22323-82-6 ]

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:

Application In Synthesis of [ 22323-82-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 22323-82-6 ]
  • Downstream synthetic route of [ 22323-82-6 ]

[ 22323-82-6 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 22323-82-6 ]
  • [ 23735-39-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3198 - 3213
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 7, p. 1163 - 1172
[3] Tetrahedron Letters, 2005, vol. 46, # 13, p. 2291 - 2294
[4] Tetrahedron Asymmetry, 1998, vol. 9, # 21, p. 3737 - 3739
[5] Tetrahedron Asymmetry, 1998, vol. 9, # 8, p. 1359 - 1367
[6] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1985, vol. 34, # 11, p. 2414 - 2415[7] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1985, # 11, p. 2605 - 2606
[8] Journal of Medicinal Chemistry, 1992, vol. 35, # 23, p. 4415 - 4424
[9] Journal of Organic Chemistry, 1992, vol. 57, # 11, p. 3365 - 3380
[10] Journal of Organic Chemistry, 1982, vol. 47, # 18, p. 3581 - 3585
[11] RSC Advances, 2018, vol. 8, # 18, p. 9587 - 9596
  • 2
  • [ 22323-82-6 ]
  • [ 114746-70-2 ]
Reference: [1] ACS Catalysis, 2018, vol. 8, # 7, p. 6738 - 6744
[2] Tetrahedron, 2005, vol. 61, # 6, p. 1459 - 1480
[3] Tetrahedron, 2007, vol. 63, # 34, p. 8255 - 8266
  • 3
  • [ 22323-82-6 ]
  • [ 98-59-9 ]
  • [ 23735-43-5 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2004, vol. 41, # 3, p. 311 - 316
[2] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 3, p. 607 - 611
[3] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 5, p. 963 - 968
  • 4
  • [ 22323-82-6 ]
  • [ 98-59-9 ]
  • [ 23788-74-1 ]
YieldReaction ConditionsOperation in experiment
99% at 0 - 20℃; p-Toluenesulfonyl chloride (6.18 g, 31.7 mmol) was added portionwise over a period of 10 min to a solution of   (S)-(+)-2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolane (19a) (4.0 g, 30.2 mmol) in anhydrous   pyridine (50 mL) in an ice bath. The resulting solution was slowly brought to room temperature and stirred overnight. During that time, a white precipitate formed. The pyridine was removed under reduced pressure and the residue was diluted with ethyl acetate (50 mL), washed subsequently with cold aqueous 1 M   HCl (2×150 mL), saturated   NaHCO3 (100 mL) and brine (200 mL). The organic layer was dried over Na2SO4, filtered and concentrated to give a light yellow   oil. The crude product was purified by column chromatography over silica gel with gradient elution 10–30percent AcOEt/hexanes to afford   (R)-(−)-3-tosyloxy-1,2-propanediol acetonide 20a (8.54 g, 99percent yield, 99.9percent ee) as a colourless viscous oil. Rf=0.37 (20percent AcOEt/hexanes). [α]D20 −4.8 (c 1.0, EtOH) (lit. [α]D24 −4.6 (c 13.0, EtOH)).25 FTIR (thin film) ν 3073, 2987, 2937, 2891, 1598, 1495, 1455, 1368, 1257, 1213, 1190, 1177, 1096, 1055, 979, 829, 788, 665, 555 cm−1. 1H NMR (600 MHz, CDCl3) δ 1.31 (s, 3H, CH3-2), 1.34 (s, 3H, CH3-2), 2.45 (s, 3H, ArCH3), 3.76 (dd, J=5.1 and 8.8 Hz, 1H, one of the CH2-5 group), 3.98 (dd, J=6.0 and 10.2 Hz, 1H, one of the CH2-1′ group), 3.99–4.05 (m, 2H, one of the CH2-1′ group and one of the CH2-5 group), 4.28 (m, 1H, CH-4), 7.35 (m, 2H, aromatic H-3 and H-5), 7.79 (m, 2H, aromatic H-2 and H-6) ppm. 13C NMR (150 MHz, CDCl3) δ 21.5 (Ar–CH3), 25.1 (CH3-2), 26.5 (CH3-2), 66.1 (C-5), 69.4 (C-1′), 72.8 (C-4), 109.9 (C-2), 127.9 (2C, aromatic C-2 and C-6), 129.8 (2C, aromatic C-3 and C-5), 132.6 (aromatic C-1), 145.0 (aromatic C-4) ppm. HRMS (ESI): calcd for C13H18NaO5S [M+Na]+ 309.07672; found 309.0762. Chiral HPLC: Chiralpak IA, 5 μm, 250×4.6 mm column, hexanes/2-propanol/methanol 97:2:1 (v/v/v), 1.0 mL/min, tR=21.71 min (0.06percent yield of 20b), tR=24.20 min (99.94percent yield of 20a), 99.88percent ee. All physical and spectroscopic data match those reported in the literature.
98.6% at 20℃; Cooling with ice />-Toluenesulfonyl chloride (6.18 g, 31.748 mmol) was added portionwise over a period of 10 min to a solution of (.S)-(+)-2,2-dimethyl-4-(hydroxymethyl)-l ,3-dioxolane (19a) (4.00 g, 30.236 mmol) in anhydrous pyridine (50.0 ml) in an ice bath. The resulting solution was slowly brought to room temperature and stirred overnight. During that time, a white precipitate formed. The pyridine was removed under reduced pressure and the residue was diluted with ethyl acetate (50 ml), washed subsequently with cold aqueous 1M HC1 (2 x 150 ml), saturated NaHC03 (100 ml) and brine (200 ml). The organic layer was dried over Na2S04, filtered and concentrated to give a light yellow oil. The crude product was purified by column chromatography over silica gel with gradient elution 10 - 30percent ethyl acetate/hexanes to afford (i?)-(-)-3-tosyloxy-l ,2-propanediol acetonide 20a (8.54 g, 98.6percent yield, 99.88percent ee) as a colourless viscosous oil. The liquid changes to a white solid at low temperatures, [erg = ^.75° (c 1.0, EtOH) (lit. [a = -4.6° (c 13.0, EtOH))12. FT-IR (thin film) vmax (cm-1): 3073, 2987, 2937, 2891, 1598, 1495, 1455, 1368, 1257, 1213, 1190, 1 177, 1096, 1055, 979, 829, 788, 665, 555. NMR (600 MHz, CDC13, 25 °C) δ (ppm): 1.31 (s, 3H, CH3-2), 1.34 (s, 3H, CH3-2), 2.45 (s, 3H, ArCH3), 3.76 (dd, J = 5.1 and 8.8 Hz, 1H, one of the CH2-5 group), 3.98 (dd, J = 6.0 and 10.2 Hz, 1H, one of the CH2-1' group), 4.01 (dd, J = 5.6 and 10.3 Hz, 1H, one of the CH2-1' group), 4.03 (dd, J = 6.2 and 8.8 Hz, 1H, one of the CH2-5 group), 4.28 (m, 1H, CH-4), 7.35 (m, 2H, aromatic H-3 and H-5), 7.79 (m, 2H, aromatic H-2 and H-6). 13C NMR (150 MHz, CDC13, 25 °C) δ (ppm): 21.54 (Ar-CH3), 25.05 (CH3-2), 26.53 (CH3-2), 66.05 (C-5), 69.44 (C-l'), 72.82 (C-4), 109.93 (C- 2), 127.88 (2C, aromatic C-2 and C-6), 129.83 (2C, aromatic C-3 and C-5), 132.55 (aromatic C-l), 144.99 (aromatic C-4). HRMS (ESI): calcd. for C13Hi805NaS [M + Na]+ 309.07672; fund 309.0762. Chiral HPLC: Chiralpak IA, 5 μιη, 250 x 4.6 mm column, hexanes/2-propanol/methanol 97:2: 1 (v/v/v), 1.0 ml/min, Rt = 21.71 min. (0.06percent yield of 20b), Rt = 24.20 (99.94percent yield of 20a), 99.88percent ee.
98.6% at 20℃; p-Toluenesulfonyl chloride (6.18 g, 31.748 mmol) was added portionwise over a period of 10 min to a solution of (S)-(+)-2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolane (19a) (4.00 g, 30.236 mmol) in anhydrous pyridine (50.0 ml) in an ice bath.
The resulting solution was slowly brought to room temperature and stirred overnight.
During that time, a white precipitate formed.
The pyridine was removed under reduced pressure and the residue was diluted with ethyl acetate (50 ml), washed subsequently with cold aqueous 1M HCl (2*150 ml), saturated NaHCO3 (100 ml) and brine (200 ml).
The organic layer was dried over Na2SO4, filtered and concentrated to give a light yellow oil.
The crude product was purified by column chromatography over silica gel with gradient elution 10-30percent ethyl acetate/hexanes to afford (R)-(-)-3-tosyloxy-1,2-propanediol acetonide 20a (8.54 g, 98.6percent yield, 99.88percent ee) as a colourless viscosous oil.
The liquid changes to a white solid at low temperatures. [α]D20=-4.75° (c 1.0, EtOH) (lit. [α]D24=-4.6° (c 13.0, EtOH))12. FT-IR (thin film) νmax (cm-1): 3073, 2987, 2937, 2891, 1598, 1495, 1455, 1368, 1257, 1213, 1190, 1177, 1096, 1055, 979, 829, 788, 665, 555. 1H NMR (600 MHz, CDCl3, 25° C.) δ (ppm): 1.31 (s, 3H, CH3-2), 1.34 (s, 3H, CH3-2), 2.45 (s, 3H, ArCH3), 3.76 (dd, J=5.1 and 8.8 Hz, 1H, one of the CH2-5 group), 3.98 (dd, J=6.0 and 10.2 Hz, 1H, one of the CH2-1' group), 4.01 (dd, J=5.6 and 10.3 Hz, 1H, one of the CH2-1' group), 4.03 (dd, J=6.2 and 8.8 Hz, 1H, one of the CH2-5 group), 4.28 (m, 1H, CH-4), 7.35 (m, 2H, aromatic H-3 and H-5), 7.79 (m, 2H, aromatic H-2 and H-6).
13C NMR (150 MHz, CDCl3, 25° C.) δ (ppm): 21.54 (Ar-CH3), 25.05 (CH3-2), 26.53 (CH3-2), 66.05 (C-5), 69.44 (C-1'), 72.82 (C-4), 109.93 (C-2), 127.88 (2C, aromatic C-2 and C-6), 129.83 (2C, aromatic C-3 and C-5), 132.55 (aromatic C-1), 144.99 (aromatic C-4). HRMS (ESI): calcd. for C13H18O5NaS [M+Na]+ 309.07672; fund 309.0762.
90.9% at 20℃; p-Toluenesulfonyl chloride (6.5 g, 34.1 mmol) was added portionwise over a period of 10 min to a solution of (£)-(+)- 1 ,2-isopropylideneglycerol (3.0 g, 22.7 mmol) and DMAP (30 mg, 0.25 mmol) in anhydrous pyridine (30 mL) in a water bath. The resulting solution was stirred overnight. The pyridine was removed under reduced pressure, and the residue was diluted with ethyl acetate (50 mL), washed subsequently with water (2 x 40mL), cold aqueous 1 M HC1 (40 mL), saturated NaHC03 (40 mL) and water (40 mL). The organic layer was dried over Mg2S04, filtered and concentrated to give a light yellow oil. The crude product was purified by column chromatography (eluent: 10percent ethyl acetate in hexane to 30percent ethyl acetate in hexane) to afford (i?)-2,2-Dimethyl-l,3-dioxolane-4- methanol p-toluenesulfonate i (5.91 g, 90.9percent yield) as a colorless viscous oil.

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[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3198 - 3213
[3] Patent: WO2013/133730, 2013, A1, . Location in patent: Page/Page column 33; 34
[4] Patent: US2015/31898, 2015, A1, . Location in patent: Paragraph 0221; 0222
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[10] Journal of Organic Chemistry, 1992, vol. 57, # 11, p. 3365 - 3380
[11] Patent: WO2015/31984, 2015, A1, . Location in patent: Page/Page column 52-53
[12] Patent: WO2017/210771, 2017, A1, . Location in patent: Paragraph 293
[13] Journal of Organometallic Chemistry, 1996, vol. 519, # 1-2, p. 93 - 101
[14] Journal of Organic Chemistry, 1990, vol. 55, # 10, p. 3129 - 3137
[15] Tetrahedron Asymmetry, 1998, vol. 9, # 8, p. 1359 - 1367
[16] Tetrahedron Asymmetry, 1998, vol. 9, # 21, p. 3737 - 3739
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  • 5
  • [ 22323-82-6 ]
  • [ 23788-74-1 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1981, vol. 29, # 12, p. 3593 - 3600
  • 6
  • [ 22323-82-6 ]
  • [ 52373-72-5 ]
Reference: [1] Helvetica Chimica Acta, 1983, vol. 66, # 3, p. 814 - 823
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