(3aR,6aR)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-one

• ChemBase ID: 148633
• Molecular Formular: C7H10O4
• Molecular Mass: 158.1519
• Monoisotopic Mass: 158.0579088
• SMILES: CC1(O[C@@H]2COC(=O)[C@@H]2O1)C
• Canonical SMILES: O=C1OC[C@@H]2[C@H]1OC(O2)(C)C
• InChI: InChI=1S/C7H10O4/c1-7(2)10-4-3-9-6(8)5(4)11-7/h4-5H,3H2,1-2H3/t4-,5-/m1/s1
• InChIKey: WHPSMBYLYRPVGU-RFZPGFLSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,6aR)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-one
• IUPAC Traditional name: (3aR,6aR)-2,2-dimethyl-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• Synonyms: (-)-2,3-O-Isopropylidene-D-erythronolactone; (3aR,6aR)-Dihydro-2,2-dimethyl-furo[3,4-d]-1,3-dioxol-4(3aH)-one; D-2,3-O-Isopropylidene-erythronic Acid γ-Lactone; 2,3-O-Isopropylidene-D-erythronolactone; (-)-2,3-O-异亚丙基-D-赤酮酸内酯

Database IDs

• CAS Number: 25581-41-3
• MDL Number: MFCD00134440
• Beilstein Number: 1282952
• PubChem SID: 162242808; 24863491
• PubChem CID: 386843

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.21782131
• LogD (pH = 7.4): 0.21782131
• Log P: 0.21782131
• Molar Refractivity: 35.0608 cm^3
• Polarizability: 14.446987 Å^3
• Polar Surface Area: 44.76 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 66-69 °C; 67-69 °C(lit.); 68-68.5°C
• Optical Rotation: [α]20/D -118°, c = 1 in H2O; [α]20/D -119±4°, c = 2% in H2O

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% (sum of enantiomers, GC); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C7H10O4

DETAILS

Sigma Aldrich - 377090

Packaging
1, 5 g in glass bottle
Application
Undergoes Aldol condensations with silyl ketene acetals.1 Employed in spiroannulated carbohydrate synthesis.2 Convergent syntheses of a hydroxylated indolizidine,3 carbohydrate substituted benzoquinones,4 and of the oxazole segment of calyculin5 have been accomplished using this chiral synthon.

Sigma Aldrich - 59430

Other Notes
Chiral building block1,2,3,4

Toronto Research Chemicals - I825000

A chiral synthon used for the synthesis of certain natural products such as the leukotrienes.

REFERENCES

• Cohen, H., et al.: J. Am. Chem. Soc., 105, 3661 (1983)
• Dardonville, C., et al.: J. Med. Chem., 47, 3427 (1983)
• El-Hamamsy, M., et al.: Bioorg. Med. Chem., 15, 4552 (1983)
• Biswas, K., et al.: Bioorg. Med. Chem. Lett., 18, 4764 (1983)