(1S,2S)-1,2-bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol

• ChemBase ID: 68467
• Molecular Formular: C12H22O6
• Molecular Mass: 262.29948
• Monoisotopic Mass: 262.14163842
• SMILES: O1C[C@@H](OC1(C)C)[C@@H](O)[C@H](O)[C@@H]1OC(OC1)(C)C
• Canonical SMILES: O[C@@H]([C@@H]([C@H]1COC(O1)(C)C)O)[C@H]1COC(O1)(C)C
• InChI: InChI=1S/C12H22O6/c1-11(2)15-5-7(17-11)9(13)10(14)8-6-16-12(3,4)18-8/h7-10,13-14H,5-6H2,1-4H3/t7-,8-,9-,10-/m1/s1
• InChIKey: ODYBCPSCYHAGHA-ZYUZMQFOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S)-1,2-bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol
• IUPAC Traditional name: (1S,2S)-1,2-bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol
• Synonyms: 1,2:5,6-Bis-O-(1-methylethylidene)-D-mannitol; D-Mannitol diacetonide; 1,2:5,6-Di-O-isopropylidene-D-mannitol; 1,2-5,6-DI-O-ISOPROPYLIDENE-D-MANNITOL; 1,2:5,6-Bis-O-(1-methylethylidene)-D-mannitol; D-(+)-1,2:5,6-Di-O-isopropylidenemannitol; D-Mannitol 1,2:5,6-Bis-acetonide; Mannitol Diacetonide; NSC 47987; NSC 67545; NSC 89874; 1,2:5,6-Di-O-isopropylidene-D-mannitol; 1,2:5,6-Diacetone-D-mannitol; 双丙酮-D-甘露糖醇; 1,2:5,6-二-O-二异亚丙基-D-甘露糖醇; 1,2:5,6-二-O-异亚丙基-D-甘露醇

Database IDs

• CAS Number: 1707-77-3
• EC Number: 216-954-8
• MDL Number: MFCD00003211
• Beilstein Number: 83765
• PubChem SID: 24857858; 24863649; 162034198
• PubChem CID: 96011

CALCULATED PROPERTIES

• Acid pKa: 12.760178
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.32516965
• LogD (pH = 7.4): -0.3251715
• Log P: -0.32516962
• Molar Refractivity: 62.8176 cm^3
• Polarizability: 25.514626 Å^3
• Polar Surface Area: 77.38 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: White Solid
• Melting Point: 120-122 °C(lit.); 120-122°C; 121-125 °C
• Optical Rotation: [α]/D +6.0±1.0°, c = 5 in chloroform; [α]20/D +6±1°, c = 5% in chloroform; +6 (c=5 in chloroform)

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (sum of enantiomers, GC); 95+%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C12H22O6

DETAILS

MP Biomedicals - 05203019

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 296406

Packaging
5, 25 g in glass bottle

Sigma Aldrich - 38410

Other Notes
Oxidative cleavage leads to isopropylidene-D-glyceraldehyde, reduction of the latter to D-1,2-isopropylideneglycerol, both important chiral building blocks; review 1; Improved oxidative cleavage 2; Oxidative cleavage to the glyceric acid 3

Toronto Research Chemicals - D458955

Nebivolol intermediate.

REFERENCES

• Ono, Y., et al.: Steroids, 71, 529 (2006)
• Kadirvel, M., et al.: Bioorg. Med. Chem. Lett., 20, 2625 (2006)
• Treatment with NaIO ₄ affords the useful synthon 2,3-O-isopropylidene-D-glyceraldehyde (glyceraldehyde acetonide): J. Org. Chem., 56, 4056 (1991); Org. Synth. Coll., 9, 450 (1998). This in turn can be homologated diastereoselectively using 2-(Trimethylsilyl)thiazole, B21903: Org. Synth. Coll., 9, 52 (1998). For use of Pb(OAc) ₄ in the formation of glyceraldehyde acetonide as a chiral precursor of cyclopropyl carbocyclic nucleosides as HIV reverse transcriptase inhibitors, see: J. Org. Chem., 60, 5236 (1995).