138381-86-9

Upstream product

• 501-53-1 benzyl chloroformate 
• 818-08-6 di(n-butyl)tin oxide 
• 144-55-8 sodium hydrogencarbonate 
• 98-59-9 p-toluenesulfonyl chloride 
• 130539-12-7 N-Benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 138381-83-6 4,6-O-(R-Benzylidene)-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol 

Downstream Products

• 150338-29-7 2-Azido-4,6-O-(R-benzylidene)-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-3-O-methanesulfonyl-D-allitol 
• 150271-32-2 2-Azido-4,6-O-(R-benzylidene)-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-3-O-methanesulfonyl-D-glucitol 
• 171334-18-2 3-Azido-4,6-O-(R-benzylidene)-N-benzyloxycarbonyl-1,3,5-trideoxy-1,5-imino-D-altritol 
• 150338-28-6 2-Azido-4,6-O-(R-benzylidene)-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-D-allitol 
• 150271-15-1 2-Azido-4,6-O-(R-benzylidene)-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-D-glucitol 
• 150271-33-3 3-O-Acetyl-2-azido-4,6-O-(R-benzylidene)-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-D-allitol 
• 150271-35-5 2-Azido-4,6-O-(R-benzylidene)-1,2,5-trideoxy-1,5-imino-N-methoxycarbonyl-3-O-methanesulfonyl-D-allitol 
• 150271-28-6 8β-Azidohexahydro-N-benzyloxycarbonyl-7-oxo-2R-2α-phenyl-5H-4,4aα,8aβ-1,3-dioxino<5,4-b>pyridine-5-carboxylate 
• 150271-26-4 4,6-O-(R-Benzylidene)-N-butyl-2-butyramido-3-O-butanoyl-1,2,5-trideoxy-1,5-imino-D-glucitol 
• 150271-39-9 2,3-Diazido-4,6-O-(R-benzylidene)-N-butyl-1,2,3,5-tetradeoxy-1,5-imino-D-glucitol 
• 171334-20-6 4,6-O-(R-Benzylidene)-N-benzyloxycarbonyl-2-fluoro-1,2,5-trideoxy-1,5-imino-D-glucitol 

Relevant academic research and scientific papers

NUCLEOPHILIC OPENING OF N-CARBOALKOXY-2,3-ANHYDRO-1-DEOXYMANNOJIRIMYCIN. A USEFUL METHOD FOR THE SYNTHESES OF 2-, 3- AND 2,3-DISUBSTITUTED 1-DEOXYNOJIRIMYCIN ANALOGS

A useful methodology for the synthesis of a number of 2-, 3- and 2,3-disubstituted deoxynojirimycin analogs is reported.It has been found that the epoxides in stereoselectively synthesized N-carboalkoxy-2,3-anhydro-1-deoxymannojirimycins (4 and 5) react with N-, S- and F-nucleophiles to give a mixture of gluco and altro products.The 3-azido altro compound (12b) yields the desired gluco derivative (40) by oxidation, in situ epimerization at C-3, followed by stereoselective reduction of the carbonyl group.The azido intermediate (12a) affords the 2,3-diazido gluco compound (51) by double inversion at C-3.Attempts have been made to understand the factors contributing to the opening of epoxides (4, 5 and 9) by different nucleophiles.

2- and 3-sulfur derivatives of 1,5-iminosugars

Novel derivatives of 1-deoxynojirimycin are disclosed which have thio or sulfinyl substituents at C-2 or C-3. These compounds are useful inhibitors of lentiviruses such as visna virus and human immunodeficiency virus. Methods of chemical synthesis of thes