(R)-(-)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE

Product Name: (R)-(-)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE
CAS No.: 23788-74-1
Chemical Name: (R)-(-)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE
Synonyms: RARECHEM AK HZ 0035;(R)-O-ISOPROPYLIDENE GLYCEROL TOSYLATE;D-α,β-Isopropylideneglycerol-γ-tosylate;(R)-3-TOSYLOXY-1,2-PROPANEDIOL ACETONIDE;1,2-ISOPROPYLIDENE-SN-GLYCEROL 3-TOSYLATE;1-O-Tosyl-2-O,3-O-isopropylidene-D-glycerin;(R)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL TOSYLATE;D-ALPHA,BETA-ISOPROPYLIDENEGLYCEROL-GAMMA-TOSYLATE;(R)-1,2-O-ISOPROPYLIDENEGLYCEROL-3-TOLUENESULFONATE;(R)-1,2-O-Isopropylideneglycerol-3-toluenesulphonate
CBNumber: CB5344527
Molecular Formula: C13H18O5S
Formula Weight: 286.34
MOL File: 23788-74-1.mol

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(R)-(-)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE Property

Melting point:: 41-43 °C(lit.)
Boiling point:: 398.71°C (rough estimate)
Density: 1.208 g/mL at 25 °C(lit.)
refractive index: n20/D 1.506(lit.)
Flash point:: >230 °F
storage temp.: -20°C
solubility: Dichloromethane; Chloroform; Ethyl Acetate; Methanol; DMF;
form: Oil
color: Pale Brown
optical activity: [α]/D 7.0±0.5°, neat
BRN: 89800
InChI: InChI=1/C13H18O5S/c1-10-4-6-12(7-5-10)19(14,15)17-9-11-8-16-13(2,3)18-11/h4-7,11H,8-9H2,1-3H3/t11-/s3
InChIKey: SRKDUHUULIWXFT-LLVKDONJSA-N
SMILES: C1(C=CC(C)=CC=1)S(=O)(=O)OC[C@H]1COC(C)(C)O1 |&1:12,r|
CAS DataBase Reference: 23788-74-1(CAS DataBase Reference)

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Safety

Hazard Codes: Xi,Xn
Risk Statements: 36/37/38-22
Safety Statements: 26-36-37/39
WGK Germany: 3
F: 10-21
HS Code: 29329900

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 59453
Product name: (R)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate
Purity: ≥99.0% (sum of enantiomers, GC)
Packaging: 5G
Price: $119
Updated: 2023/06/20

Sigma-Aldrich

Product number: 59453
Product name: (R)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate
Purity: ≥99.0% (sum of enantiomers, GC)
Packaging: 25g
Price: $565
Updated: 2023/06/20

TCI Chemical

Product number: D2549
Product name: (R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate
Purity: >98.0%(GC)
Packaging: 1g
Price: $47
Updated: 2025/07/31

TRC

Product number: D464975
Product name: (R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate
Packaging: 5g
Price: $340
Updated: 2021/12/16

TRC

Product number: D469553
Product name: (R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate
Packaging: 5g
Price: $875
Updated: 2021/12/16

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(R)-(-)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE Chemical Properties,Usage,Production

Chemical Properties

clear yellow to light brown viscous liquid

Uses

(R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate is a chiral building block. It is used to prepare the antifungal agent ketoconazole. It is also used to prepare acyclic Nucleotide Analogs Derived from 8-Azapurines with antiviral activities.

Synthesis

22323-82-6

98-59-9

23788-74-1

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) was added p-toluenesulfonyl chloride (6.18 g, 31.7 mmol) in batches over a period of 10 min under ice bath conditions. The reaction mixture was slowly brought to room temperature and stirred overnight, during which a white precipitate was observed to form. Upon completion of the reaction, the pyridine was removed under reduced pressure and the residue was diluted with ethyl acetate (50 mL) and washed sequentially with cold aqueous 1M HCl solution (2 x 150 mL), saturated NaHCO3 solution (100 mL) and brine (200 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated to give a light yellow oil. The crude product was purified by silica gel column chromatography using a 10-30% ethyl acetate/hexane gradient elution to afford (R)-(-)-3-toluenesulfonyloxy-1,2-propanediol acetone compound (20a) (8.54 g, 99% yield, 99.9% ee) as a colorless viscous oily substance. rf = 0.37 (20% ethyl acetate/hexanes). [α]D20 -4.8 (c 1.0, EtOH) (literature value [α]D24 -4.6 (c 13.0, EtOH)). ftir (film) νmax 3073, 2987, 2937, 2891, 1598, 1495, 1455, 1368, 1257, 1213, 1190, 1177, 1096, 1055 , 979, 829, 788, 665, 555 cm-1.1H NMR (600MHz, CDCl3) δ1.31(s, 3H, CH3-2), 1.34(s, 3H, CH3-2), 2.45(s, 3H, ArCH3), 3.76(dd, J=5.1 and 8.8Hz, 1H, CH2-5), 3.98 (dd, J=6.0 and 10.2 Hz, 1H, CH2-1'), 3.99-4.05 (m, 2H, CH2-1' and CH2-5), 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 ( 150MHz, CDCl3) δ21.5(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(m, 2H, aromatic C-3 and C-6) ppm. HRMS (ESI): C13H18NaO5S [M+Na]+ Calculated value 309.07672; Measured value 309.0762 Chiral HPLC analysis: Chiralpak IA column (5 μm, 250×4.6 mm), mobile phase hexane/2-propanol/methanol (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. Chiralpak IA column (5 μm, 250×4.6 mm), mobile phase hexane/2-propanol/methanol (97:2:1, v/v/v), flow rate 1.0 mL/min, tR=21.71 min (0.06% 20b), tR=24.20 min (99.94% 20a), 99.88% ee. All physical and spectroscopic data are in good agreement with those reported in the literature.

References

[1] Tetrahedron, 2013, vol. 69, # 5, p. 1634 - 1648
[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
[5] Pharmazie, 1998, vol. 53, # 6, p. 377 - 380

(R)-(-)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE Preparation Products And Raw materials

Raw materials

Preparation Products

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(R)-(-)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE Suppliers

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View Lastest Price from (R)-(-)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE manufacturers

Shaanxi Dideu New Materials Co. Ltd

Product: (R)-(-)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE 23788-74-1
Price: US $0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 10000KGS
Release date: 2025-02-18

Career Henan Chemical Co

Product: 1,3-Dioxolane-4-methanol,2,2-dimethyl-, 4-(4-methylbenzenesulfonate), (4R)- 23788-74-1
Price: US $9.80/KG
Min. Order: 1KG
Purity: ≥98%
Supply Ability: 20 tons
Release date: 2020-01-09

23788-74-1, (R)-(-)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATERelated Search:

(R)-2-(2-(methylthio)ethyl)azetidine-2-carboxylic acid (R)-2-Octyl 4-[4-(Hexyloxy)benzoyloxy]benzoate (R)-2-(2-(methylthio)ethyl)pyrrolidine-2-carboxylic acid (R)-2-(2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)ethan-1-ol (R)-2-((2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)methyl)-6-(trifluoromethyl)phenol ((R)-morpholin-2-yl)methanol (R)-2-(hydroxymethyl)-1-methylpiperazine (-)-1,4-DI-O-TOSYL-2,3-O-ISOPROPYLIDENETHREITOL (S)-(+)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE (R)-(-)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE cis-[2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl-p-toluenesulfonate 2,2-DIMETHYL-1,3-DIOXOLANE Methyl p-toluenesulfonate 1,3-Dioxolane-4-methanol (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol 2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE 2,3-O-Isopropylidene-1,6-ditosyl-L-sorbose (-)-TRANS-1-O-TOSYL-2,3-ISOPROPYLIDENE-L-THREITOL

p-Toluenesulfonic acid [(R)-2,2-dimethyl-1,3-dioxolane-4β-yl]methyl ester

p-Toluenesulfonic acid [R,(-)]-2,2-dimethyl-1,3-dioxolan-4-ylmethyl ester

p-Toluenesulfonic acid [R,(-)]-2,2-dimethyl-1,3-dioxolane-4-ylmethyl ester

(R)-(-)-2,2-Dimethyl-4-(hydroxymethyl)-1,3-dioxolane-p-toluenesulfonate,97%

p-Toluenesulfonic acid ((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl ester

Toluene-4-sulfonic acid ((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)methyl ester

D-α,β-Isopropylideneglycerol-γ-tosylate

[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzene-1-sulfonate

1,3-Dioxolane-4-methanol,2,2-dimethyl-, 4-(4-methylbenzenesulfonate), (4R)-

D-(-)-1,2-ISOPROPYLIDENEGLYCEROL 3-(P-TOLUENESULFONATE)

(R)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate >=99.0% (sum of enantiomers, GC)

(R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate

(R)-1,2-O-ISOPROPYLIDENEGLYCEROL-3-TOLUENESULFONATE

(R)-(-)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE

(R)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL-4-METHYLBENZENESULFONATE

(R)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL TOLUENE-4-SULFONATE

(R)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL TOSYLATE

(R)-(-)-2,2-DIMETHYL-1,3-DIOXOLANE-4-YLMETHYL P-TOLUENESULFATE

(R)-(-)-2,2-DIMETHYL-1,3-DIOXOLANE-4-YLMETHYL P-TOLUENESULFONATE

(R)-(-)-2,2-DIMETHYL-4-(HYDROXYMETHYL)-1,3-DIOXOLANE-P-TOLUENESULFONATE

(R)-2,2-DIMETHYL-4-(HYDROXYMETHYL)-1,3-DIOXOLANE-P-TOLUENESULFONATE

(R)-(-)-2,2-DIMETHYL-4-(HYDROXYMETHYL)-1,3-DIOXOLANE-P-TOLUENSULFONATE

(R)-3-TOSYLOXY-1,2-PROPANEDIOL ACETONIDE

RARECHEM AK HZ 0035

(R)-O-ISOPROPYLIDENE GLYCEROL TOSYLATE

(R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-ylmethyl p-toluenosulfate

(R)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate

(R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol-4-toluenesulfonate

(r)-2,2-dimethyl-1,3-dioxolane-4-methyl p-toluenesulfonate

(R)-1,2-O-Isopropylideneglycerol-3-toluenesulphonate 95%

1,2-Isopropylidene-sn-glycerol 3-tosylate, D-α,β-Isopropylideneglycerol-γ-tosylate

1,2-Isopropylidene-sn-glycerol 3-tosylate, (R)-2,2-Dimethyl-1,3-dioxolane-4-methyl p-toluenesulfonate, D-α,β-Isopropylideneglycerol γ-tosylate

1-O-Tosyl-2-O,3-O-isopropylidene-D-glycerin

4-Methylbenzenesulfonic acid (R)-2,2-dimethyl-1,3-dioxolane-4β-ylmethyl ester

p-Toluenesulfonic acid [(4R)-2,2-dimethyl-1,3-dioxolane-4-yl]methyl ester

1,3-DIOXOLANE-4-METHANOL, 2,2-DIMETHYL-, 4-METHYLBENZENESULFONATE, (4R)-

1,2-ISOPROPYLIDENE-SN-GLYCEROL 3-TOSYLATE

D-ALPHA,BETA-ISOPROPYLIDENEGLYCEROL-GAMMA-TOSYLATE

(R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethylp-Toluenesulfonate&gt

(R)-(-)-2,2-Dimethyl-4-(hydroxymethyl)-1,3-dioxolane-p-tolue...

(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl (R)-4-Methylbenzenesulfonate

(R)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate

(R)-1,2-O-Isopropylideneglycerol-3-toluenesulphonate

23788-74-1

Cd3H19O5S

C13H18O5S

Protected Alcohols

Organic Building Blocks

Dioxolanes

Chiral Building Blocks

Dioxanes & Dioxolanes

Glycidyl Compounds, etc. (Chiral)

Asymmetric Synthesis

chiral

Chiral Building Blocks

Dioxanes & Dioxolanes

Dioxolanes

Glycidyl Compounds, etc. (Chiral)