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

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

Uses

Used in Organic Synthesis:
5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone is used as a synthetic intermediate for the creation of various organic compounds. The presence of the azido and tert-butyldimethylsilyl groups allows for specific reactions and modifications, facilitating the synthesis of new molecules with potential applications in various fields.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone is utilized as a key component in the development of novel drugs. Its unique structure and reactivity enable the design and synthesis of innovative therapeutic agents, potentially leading to breakthroughs in the treatment of various diseases and conditions.
Used in Chemical Modification:
5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone is employed as a modifying agent to alter the properties of other molecules. The azido and tert-butyldimethylsilyl groups can be used to attach or modify functional groups, enabling the development of new compounds with improved characteristics and applications.
Used in Material Science:
In the field of material science, 5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone is utilized as a building block for the synthesis of advanced materials. Its unique structure and reactivity contribute to the development of new materials with enhanced properties, such as improved stability, reactivity, or selectivity.
Used in Analytical Chemistry:
5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone is employed as a reagent or reference compound in analytical chemistry. Its distinctive properties make it suitable for use in various analytical techniques, such as chromatography, spectroscopy, or electrochemistry, to study and characterize other compounds.

Upstream product

• 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 
• 118464-47-4 6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-L-gulonolactone 
• 94840-08-1 2,3-O-isopropylidene-L-gulono-γ-lactone 
• 1128-23-0 L-gulono-1,4-lactone 
• 7306-64-1 2,3:5,6-di-O-isopropylidene-L-gulonolactone 

Downstream Products

• 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 
• 109944-15-2 kifunensine 
• 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 
• 128741-75-3 (2R,3R,4R,5R)-2,3:4,6-di(isopropylidenedioxy)-5-oxamoylaminohexanol 
• 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 

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.

A practical synthesis of kifunensine analogues as inhibitors of endoplasmic reticulum α-mannosidase I

A practical synthesis of the potent class I α-mannosidase inhibitor kifunensine (1) beginning from the inexpensive and readily available starting material L-ascorbic acid (15) is described. The protected amino-alcohol ((2R,3R,4R,5R)-5-amino-2,3:4,6-diisop

Method for synthesis of deoxymannojirimycin

A method is disclosed for the chemical synthesis of 1,5-dideoxy-1,5-imino-D-mannitol or 1,5-dideoxy-1,5-imino-L-mannitol from, respectively, 2,3-O-isopropylidene-L-gulono-γ-lactone or 2,3-O-isopropylidene-D-gulono-γ-lactone which comprises carrying out interconversion between the L-gulono and D-mannono forms or between the D-gulono and L-mannono forms, respectively, and connecting of C-1 to C-5 by nitrogen.

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.