122371-65-7

Basic information

• Product Name: N-BOC-1,5-IMINO-D-GLUCITOL
• Synonyms: N-BOC-1,5-IMINO-D-GLUCITOL;(2R,3R,4R,5S)-3,4,5-Trihydroxy-2-(hydroxyMethyl)-1-piperidinecarboxylic Acid 1,1-DiMethylethyl Ester;N-(tert-Butoxylcarbonyl)Moranoline
• CAS NO: 122371-65-7
• Molecular Formula: C₁₁H₂₁NO₆
• Molecular Weight: 295.28634
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 122371-65-7.mol

Chemical Properties

• Melting Point: 126-127°C
• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: N-BOC-1,5-IMINO-D-GLUCITOL(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-1,5-IMINO-D-GLUCITOL(122371-65-7)
• EPA Substance Registry System: N-BOC-1,5-IMINO-D-GLUCITOL(122371-65-7)

Safety Data

• Hazardous Substances Data: 122371-65-7(Hazardous Substances Data)

Usage

Chemical Properties

Brown Solid

Upstream product

• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 945394-84-3 6-azido-6-deoxy-1-O-benzyl-2,3-O-isopropylidene-α-L-sorbofuranose 
• 17682-70-1 2,3:4,6-bis-O-isopropylidene-L-sorbose 
• 74342-16-8 1-O-benzyl-2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose 
• 1262984-78-0 N-Boc-tetra-O-benzyl-1-deoxynojirimycin 
• 164024-55-9 1-O-benzyl-2,3-O-isopropylidene-α-L-sorbofuranose 
• 945394-86-5 6-azido-6-deoxy-1-O-benzyl-α-L-sorbofuranose 

Downstream Products

• 945394-89-8 N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol 
• 1262984-87-1 N-Boc-2,3,4,6-tetra-O-benzoyl-1-deoxynojirimycin 
• 945394-91-2 2-benzoyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol 
• 945395-01-7 2-O-allyl-3-O-benzyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol 
• 945394-95-6 3-O-benzyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol 
• 945394-93-4 2-benzoyl-3-O-benzyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol 

Relevant articles and documents

Quantifying Electronic Effects of Common Carbohydrate Protecting Groups in a Piperidine Model System

A study of the substituent effects of protecting groups in hydroxypiperidines was carried out and compared with the electronic effects in glycosylation chemistry. 1-Deoxynojirimycin, the aza-sugar analogue of 1-deoxy-D-glucose, was used as a carbohydrate

Selective protecting group manipulations on the 1-deoxynojirimycin scaffold

Iminosugars are inhibitors of glycoprocessing and are of interest as scaffolds for medicinal chemistry, as their successful application as peptide mimetics has shown. The synthesis of novel peptidomimetics based on 1-deoxynojirimycin (DNJ) requires practical strategies that allow introduction of amino acid side chains or pharmacophore groups at each of its hydroxyl groups or to the nitrogen atom. This paper describes one approach towards achieving selective protection and deprotection at the hydroxyl and amino groups of?DNJ and a novel synthesis of DNJ from l-sorbose is included.