118464-49-6

Basic information

• Product Name: 5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone
• Synonyms: 5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone;5-Azido-5-deoxy-6-O-[(1,1-diMethylethyl)diMethylsilyl]-2,3-O-(1-Methylethylidene)-D-Mannonic Acid γ-lactone;5-Azido-6-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-gulono-1,4-lactone
• CAS NO: 118464-49-6
• Molecular Formula: C₁₅H₂₇N₃O₅Si
• Molecular Weight: 373.47688
• Product Categories: Carbohydrates & Derivatives
• Mol File: 118464-49-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone(118464-49-6)
• EPA Substance Registry System: 5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone(118464-49-6)

Safety Data

• Hazardous Substances Data: 118464-49-6(Hazardous Substances Data)

Usage

General Description

5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone is a chemical compound that is used in organic synthesis and pharmaceutical research. It is a derivative of L-gulono-1,4-lactone, which is a precursor to vitamin C in the body. The addition of the azido group and tert-butyldimethylsilyl group to the lactone ring allows for specific reactions and modifications to be made to the molecule, making it useful for creating new compounds in the laboratory. The isopropylidene group also adds stability to the molecule, making it easier to handle and store. Overall, 5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone is a versatile and important chemical in the field of organic chemistry and pharmaceutical research.

Upstream product

• 7306-64-1 2,3:5,6-di-O-isopropylidene-L-gulonolactone 
• 1128-23-0 L-gulono-1,4-lactone 
• 118464-47-4 6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-L-gulonolactone 
• 118464-48-5 Trifluoro-methanesulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-((3aS,4S,6aS)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethyl ester 
• 94840-08-1 2,3-O-isopropylidene-L-gulono-γ-lactone 

Downstream Products

• 14199-63-4 1-deoxymannojirimycin 
• 62362-63-4 D-Mannonolactam 
• 125711-57-1 β-1-C-phenyl-deoxymannojirimycin 
• 126354-74-3 (3aR,4S,6R,7R,7aS)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-4-phenyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol 
• 128741-75-3 (2R,3R,4R,5R)-2,3:4,6-di(isopropylidenedioxy)-5-oxamoylaminohexanol 
• 134234-43-8 (3aR,3bS,6bR,10aR,10bS)-2,2,9,9-tetramethyl-1,3,8,10-tetraoxacyclohexa[e]cyclopenta[g]-5,6-dion-4-azaindolizidine 
• 109944-15-2 kifunensine 
• 872038-13-6 (3aR,3bS,6bR,10aR,10bS)-2,2,9,9-tetramethyl-1,3,8,10-tetraoxacyclohexa[e]cyclopenta[g]-5,6-dione-4-cyclohexylazaindolizidine 

Relevant articles and documents

Synthesis method of mannosidase inhibitor Kifunensine

The invention provides a synthesis method of mannosidase inhibitor Kifunensine. L-gulonic acid-gamma-lactone, which is cheap and easily available, is taken as an initial raw material to efficiently obtain the Kifunensine through multi-step chemical conversion, the overall yield of the reaction is high, reagents used in the process are cheap and easily available, and multiple steps in the synthesis process can be fed by a one-pot method, so that the operation is simple and convenient, and the method has a better industrial prospect.

PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND MANNONOLACTAM FROM L-GULONOLACTONE. SYNTHESIS OF L-DEOXYMANNOJIRIMYCIN AND L-MANNONOLACTAM FROM D-GULONOLACTONE.

An eight step synthesis of deoxymannojirimycin from L-gulonolactone in 25percent overall yield is reported; the key step is the formation of a δ-lactam by the reduction of a 5-azidolactone.The preparations of mannonolactam from L-gulonolactone and of L-deoxymannojirimycin and L-mannonolactam from D-gulonolactone are described.

SHORT SYNTHESES OF D-DEOXYMANNOJIRIMYCIN AND D-MANNOLACTAM FROM L-GULONOLACTONE AND OF L-DEOXYMANNOJIRIMYCIN AND L-MANNONOLACTAM FROM D-GULONOLACTONE

Short syntheses of D-deoxymannojirimycin and of D-mannolactam from L-gulonolactone are reported; identical sequences on D-gulonolactone lead to L-deoxymannojirimycin and L-mannolactam.