(2R)-1-(benzyloxy)-3-[(4-methylbenzenesulfonyl)oxy]propan-2-ol

• ChemBase ID: 144894
• Molecular Formular: C17H20O5S
• Molecular Mass: 336.4027
• Monoisotopic Mass: 336.10314474
• SMILES: Cc1ccc(cc1)S(=O)(=O)OC[C@@H](COCc1ccccc1)O
• Canonical SMILES: O[C@@H](COS(=O)(=O)c1ccc(cc1)C)COCc1ccccc1
• InChI: InChI=1S/C17H20O5S/c1-14-7-9-17(10-8-14)23(19,20)22-13-16(18)12-21-11-15-5-3-2-4-6-15/h2-10,16,18H,11-13H2,1H3/t16-/m1/s1
• InChIKey: HBMUWOSOGHUWSS-MRXNPFEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-1-(benzyloxy)-3-[(4-methylbenzenesulfonyl)oxy]propan-2-ol
• IUPAC Traditional name: (2R)-1-(benzyloxy)-3-[(4-methylbenzenesulfonyl)oxy]propan-2-ol
• Synonyms: (R)-(-)-1-Benzyloxy-3-tosyloxy-2-propanol; (R)-(-)-3-Benzyloxy-1,2-propanediol 1-(p-toluenesulfonate); 1-Benzyl-sn-glycerol 3-tosylate; (R)-(-)-1-Benzyloxy-3-(p-tosyloxy)-2-propanol; (R)-(-)-3-Benzyloxy-1,2-propanediol 1-(p-toluenesulfonate); (R)-(-)-3-苄氧基-1,2-丙二醇 1-(对甲苯磺酸酯); (R)-(-)-1-苄氧基-3-甲苯磺酰氧基-2-丙醇; 1-苄基-sn-甘油 3-甲苯磺酸酯; (R)-(-)-1-苄氧基-3-(对甲苯磺酰氧基)-2-丙醇; (R)-(-)-3-苄氧基-1,2-丙二醇 1-(对甲苯磺酸酯)

Database IDs

• CAS Number: 23214-66-6
• MDL Number: MFCD00134285
• Beilstein Number: 2224639
• PubChem SID: 162239106; 24862464
• PubChem CID: 13644871

CALCULATED PROPERTIES

• Acid pKa: 13.6128025
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.0926974
• LogD (pH = 7.4): 3.0926971
• Log P: 3.0926974
• Molar Refractivity: 87.8226 cm^3
• Polarizability: 35.198048 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 52-55 °C; 52-55 °C(lit.)
• Flash Point: 110 °C; 230 °F
• Optical Rotation: [α]20/D -7.3±1°, c = 10% in toluene; [α]25/D -7°, c = 10 in toluene

Safety Information

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

Product Information

• Purity: ≥90% (sum of enantiomers, HPLC); 95%
• Grade: technical
• Linear Formula: CH3C6H4SO3CH2CH(OH)CH2OCH2C6H5
• Empirical Formula (Hill Notation): C17H20O5S

DETAILS

Sigma Aldrich - 364886

Packaging
5 g in glass bottle
Application
Reagent employed in enantioselective carbohydrate, terpene, and alkaloid syntheses.1

Sigma Aldrich - 13748

Other Notes
Chiral building block for the synthesis of glycerides1