CAS 1707-77-3|(1S,2S)-1,2-bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol|(1S,2S)-1,2-bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol|1,2-5,6-DI-O-ISOPROPYLIDENE-D-MANNITOL|1,2:5,6-B...

General Information

Structure

Molecular Formula

C₁₂H₂₂O₆

Molecular Mass

262.29948

Exact Mass

262.14163842

Charge

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

Canonic Smiles

O[C@@H]([C@@H]([C@H]1COC(O1)(C)C)O)[C@H]1COC(O1)(C)C

Isomeric Smiles

O1C[C@@H](OC1(C)C)[C@@H](O)[C@H](O)[C@@H]1OC(OC1)(C)C

Calculated Properties

JChem

Acid pKa

12.760178

H Acceptors

H Donor

LogD (pH = 5.5)

-0.32516965

LogD (pH = 7.4)

-0.3251715

Log P

-0.32516962

Molar Refractivity

62.8176

Polarizability

25.514626

Polar Surface Area

77.38

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

1,2-5,6-DI-O-ISOPROPYLIDENE-D-MANNITOL1,2:5,6-Bis-O-(1-methylethylidene)-D-mannitol1,2:5,6-Di-O-isopropylidene-D-mannitol双丙酮-D-甘露糖醇D-Mannitol diacetonide1,2:5,6-二-O-二异亚丙基-D-甘露糖醇1,2:5,6-Diacetone-D-mannitol1,2:5,6-二-O-异亚丙基-D-甘露醇D-(+)-1,2:5,6-Di-O-isopropylidenemannitolNSC 47987NSC 67545NSC 898741,2:5,6-Di-O-isopropylidene-D-mannitolMannitol Diacetonide1,2:5,6-Bis-O-(1-methylethylidene)-D-mannitolD-Mannitol 1,2:5,6-Bis-acetonide

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

Names and Identifiers

Registration numbers

CAS Number

1707-77-3

PubChem SID

2486364924857858162034198

Beilstein Number

EC Number

MDL Number

PubChem CID

Registration numbers

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

MP Biomedicals

05203019

MP Biomedicals Rare Chemical collection

Sigma Aldrich

296406

Packaging
5, 25 g in glass bottle

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

TRC

D458955

Nebivolol intermediate.

Molecule Details

References

PubChem Literature

From Data Sources

• 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).

References

Bioactivity

PubChem BioAssay

Bioactivity