[(4R,5R)-2,2-dimethyl-5-{[(4-methylbenzenesulfonyl)oxy]methyl}-1,3-dioxolan-4-yl]methyl 4-methylbenzene-1-sulfonate

• ChemBase ID: 149111
• Molecular Formular: C21H26O8S2
• Molecular Mass: 470.55634
• Monoisotopic Mass: 470.10690979
• SMILES: Cc1ccc(cc1)S(=O)(=O)OC[C@@H]1[C@H](OC(O1)(C)C)COS(=O)(=O)c1ccc(cc1)C
• Canonical SMILES: CC1(C)O[C@@H]([C@H](O1)COS(=O)(=O)c1ccc(cc1)C)COS(=O)(=O)c1ccc(cc1)C
• InChI: InChI=1S/C21H26O8S2/c1-15-5-9-17(10-6-15)30(22,23)26-13-19-20(29-21(3,4)28-19)14-27-31(24,25)18-11-7-16(2)8-12-18/h5-12,19-20H,13-14H2,1-4H3/t19-,20-/m1/s1
• InChIKey: KPFDKWNWYAXRNJ-WOJBJXKFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4R,5R)-2,2-dimethyl-5-{[(4-methylbenzenesulfonyl)oxy]methyl}-1,3-dioxolan-4-yl]methyl 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: [(4R,5R)-2,2-dimethyl-5-{[(4-methylbenzenesulfonyl)oxy]methyl}-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate
• Synonyms: (+)-2,3-O-Isopropylidene-1,4-di-O-tosyl-D-threitol; (+)-2,3-O-Isopropylidene-D-threitol 1,4-ditosylate; (4R,5R)-4,5-Bis(tosyloxymethyl)-2,2-dimethyl-1,3-dioxolane; 2,3-Isopropylidene-D-threitol 1,4-ditosylate; 1,4-Di-O-tosyl-2,3-O-isopropylidene-D-threitol; (+)-1,4-Di-O-tosyl-2,3-O-isopropylidene-D-threitol; (+)-2,3-O-异亚丙基-1,4-二-O-甲苯磺酰基-D-苏糖醇; (+)-2,3-O-异亚丙基-D-苏糖醇 1,4-二甲苯磺酸酯; (4R,5R)-4,5-双(甲苯磺酰氧甲基)-2,2-二甲基-1,3-二氧戊环; 2,3-异亚丙基-D-苏糖醇 1,4-二甲苯磺酸酯; 1,4-二-O-甲苯磺酰基-2,3-O-异亚丙基-D-苏糖醇; (+)-1,4-二-O-甲苯磺酰基-2,3-O-异亚丙基-D-苏糖醇

Database IDs

• CAS Number: 51064-65-4
• EC Number: 256-943-5
• MDL Number: MFCD00063235
• Beilstein Number: 99611
• PubChem SID: 162243279; 24867467; 24854922
• PubChem CID: 97446

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 4.361299
• LogD (pH = 7.4): 4.361299
• Log P: 4.361299
• Molar Refractivity: 114.571 cm^3
• Polarizability: 46.74479 Å^3
• Polar Surface Area: 105.2 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 89-91 °C(lit.); 90-92 °C
• Optical Rotation: [α]20/D +12.1°, c = 8.8 in chloroform; [α]20/D +12.5±0.5°, c = 8.8% in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (HPLC); 97%
• Grade: purum
• Empirical Formula (Hill Notation): C21H26O8S2

DETAILS

Sigma Aldrich - 248223

Packaging
5 g in glass bottle

Sigma Aldrich - 43875

Other Notes
Chiral building block ex tartaric acid1; Precursor for a variety of chiral diphosphines, sulfoxides and arsines2; Synthesis of chiral annelated cyclopentadienes3