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2,3,5-Tri-O-benzyl-D-ribono-1,4-lactone

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

2,3,5-Tri-O-benzyl-D-ribono-1,4-lactone is a key intermediate used in the synthesis of antiviral drugs such as Ribavirin.

Category

Others

Catalog number

BAT-008977

CAS number

55094-52-5

Molecular Formula

C26H26O5

Molecular Weight

418.48

Specification
Reference Reading

IUPAC Name

(3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-one

Synonyms

AK-77581; (3R,4R,5R)-3,4-Bis(benzyloxy)-5-((benzyloxy)methyl)dihydrofuran-2(3H)-one; 2-O,3-O,5-O-Tribenzyl-D-ribonic acid gamma-lactone; 2,3,5-Tri-O-benzyl-D-ribonolactone

Appearance

White to Pale Yellow Solid

Purity

≥95% by HPLC

Density

1.21±0.1 g/cm3 (Predicted)

Melting Point

53-55°C

Boiling Point

576.8±50.0°C (Predicted)

Storage

Store at -20°C

Solubility

Soluble in Chloroform (Sparingly), DMSO (Slightly, Sonicated), Methanol (Slightly)

InChI

InChI=1S/C26H26O5/c27-26-25(30-18-22-14-8-3-9-15-22)24(29-17-21-12-6-2-7-13-21)23(31-26)19-28-16-20-10-4-1-5-11-20/h1-15,23-25H,16-19H2/t23-,24-,25-/m1/s1

InChI Key

LDHBSABBBAUMCZ-UBFVSLLYSA-N

Canonical SMILES

C1=CC=C(C=C1)COCC2C(C(C(=O)O2)OCC3=CC=CC=C3)OCC4=CC=CC=C4

1.The synthesis of 4-deazaformycin A.

Kourafalos VN1, Marakos P, Pouli N, Townsend LB. J Org Chem. 2003 Aug 8;68(16):6466-9.

The preparation of 4-deazaformycin A has been achieved. The synthesis features the condensation of a suitably substituted, lithiated 4-picoline with 2,3,5-tri-O-benzyl-d-ribonolactone, dehydration of the resulting hemiacetal, and ionic hydrogenation, followed by manipulation of the protecting groups and subsequent ring closure with the formation of 7-amino-3-(beta-d-ribofuranosyl)pyrazolo[3,4-c]pyridine.