CAS 17401-06-8

(-)-1,4-di-O-benzyl-L-threitol

Description:

(-)-1,4-di-O-benzyl-L-threitol is a chiral organic compound characterized by its structure, which includes two benzyl groups attached to a threitol backbone. This compound is a sugar alcohol derivative, specifically a diol, and is known for its potential applications in organic synthesis and as a chiral building block in the pharmaceutical industry. The presence of the benzyl groups enhances its hydrophobic properties, making it less soluble in water compared to its unmodified counterparts. (-)-1,4-di-O-benzyl-L-threitol can participate in various chemical reactions, including oxidation and reduction, due to its hydroxyl functional groups. Its chirality is significant in biological systems, as it may exhibit different biological activities compared to its enantiomer. The compound is typically handled with standard laboratory safety precautions, as with many organic chemicals, and is stored under conditions that prevent degradation. Overall, its unique structural features and properties make it a valuable compound in synthetic organic chemistry.

Formula: C₁₈H₂₂O₄

InChI: InChI=1/C18H22O4/c19-17(13-21-11-15-7-3-1-4-8-15)18(20)14-22-12-16-9-5-2-6-10-16/h1-10,17-20H,11-14H2/t17-,18-/m0/s1

SMILES: c1ccc(cc1)COC[C@@H]([C@H](COCc1ccccc1)O)O

Synonyms:

• (2S,3S)-()-1,4-Dibenzyloxy-2,3-butanediol
• (2S,3S)-1,4-bis(benzyloxy)butane-2,3-diol

(-)-1,4-Di-O-benzyl-L-threitol

CAS: 17401-06-8

Formula: C₁₈H₂₂O₄

Purity: >98.0%(GC)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 302.37

Ref: 3B-D2240

2,3-Butanediol, 1,4-bis(phenylmethoxy)-, (2S,3S)-

CAS: 17401-06-8

Formula: C₁₈H₂₂O₄

Purity: 98%

Color and Shape: Solid

Molecular weight: 302.3649

Ref: IN-DA001ZDS

(-)-1,4-Di-O-benzyl-L-threitol

CAS: 17401-06-8

(-)-1,4-Di-O-benzyl-L-threitol is an organic compound that belongs to the group of homochiral compounds. It can be synthesized from l-tartaric acid and benzaldehyde. The reaction starts with a base addition to the carbonyl group of the acid, followed by nucleophilic attack at the carbonyl carbon by a hydroxyl group on the benzaldehyde. This reaction is mechanistic, showing electron transfer as well as desymmetrization. (-)-1,4-Di-O-benzyl-L-threitol can be used for asymmetric synthesis of alkanes and tetrahydrofurans without requiring any chiral reagents or catalysts. It has also been shown to react with acetone and ethylene glycol in dioxolane and alkylation reactions.

Formula: C₁₈H₂₂O₄

Purity: Min. 95%

Molecular weight: 302.36 g/mol

Ref: 3D-MD59967