156764-21-5

Basic information

• Product Name: 3,4-di-O-benzyl-1,6-di-O-toluenesulfonyl-D-mannitol
• Synonyms: 3,4-di-O-benzyl-1,6-di-O-toluenesulfonyl-D-mannitol
• CAS NO: 156764-21-5
• Molecular Weight: 670.802
• Mol File: 156764-21-5.mol

Chemical Properties

• CAS DataBase Reference: 3,4-di-O-benzyl-1,6-di-O-toluenesulfonyl-D-mannitol(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-di-O-benzyl-1,6-di-O-toluenesulfonyl-D-mannitol(156764-21-5)
• EPA Substance Registry System: 3,4-di-O-benzyl-1,6-di-O-toluenesulfonyl-D-mannitol(156764-21-5)

Safety Data

• Hazardous Substances Data: 156764-21-5(Hazardous Substances Data)

Upstream product

• 36199-02-7 3,4-di-O-benzyl-D-mannitol 
• 98-59-9 p-toluenesulfonyl chloride 
• 69-65-8 mannitol 
• 111476-62-1 3,4-di-O-benzyl-1,2:5,6-di-O-isopropylidene-D-mannitol 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 

Downstream Products

• 151477-86-0 1,6-diazido-1,6-dideoxy-3,4-di-O-benzyl-D-mannitol 
• 215930-48-6 (2R,3R,4R,5R)-3,4-dibenzyloxyhexane-2,5-diol 
• 157363-85-4 1,2:5,6-Dianhydro-3,4-di-O-benzyl-D-mannitol 
• 156764-32-8 (2S,2'S)-<(1R,2R)-1,2-dibenzyloxy-ethan-diyl>bis(1-benzyloxycarbonyl)-aziridine 
• 156764-24-8 (2S,3R,4R,5R)-2-Azidomethyl-3,4-bis-benzyloxy-5-(tert-butoxycarbonylamino-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 156856-23-4 (2S,2'S)-<(1R,2R)-1,2-dibenzyloxy-ethan-diyl>bis(1-tert-butoxycarbonyl)-aziridine 
• 502699-56-1 (2S,2'S)-<(1R,2R)-1,2-dibenzyloxy-ethan-diyl>bis-aziridine 
• 215930-44-2 1,2-bis((4S,5S,6S,7S)-5,6-dibenzyloxy-4,7-dimethylphospholanyl)-benzene 
• 283165-43-5 (ρ,5S,6S,7R)-5,6-bis(benzyloxy)-4,7-dibenzyl[1,3,2]-dioxathiepane 2,2-dioxide 
• 283165-42-4 (2R,3R,4R,5R)-1,6-diphenyl-3,4-di-O-benzylhexane-2,3,4,5-tetrol 

Relevant articles and documents

Synthesis of chiral hydroxyl phospholanes from D-mannitol and their use in asymmetric catalytic reactions

Chiral hydroxyl monophosphane 3 [(2S,3S,4S,5S)-3,4-dihydroxy-2,5-dimethyl-1-phenylphospholane] and bisphospholanes 5a [1,2-bis[(2S,3S,4S,5S)-3,4-dihydroxy-2,5-dimethylphospholanyl]benzene] and 5b [1,2-bis[(2S,3S,4S,5S)-2,5-diethyl-3,4-dihydroxyphospholanyl]benzene] were synthesized from readily available D-mannitol in high yields. Strategies for protection and deprotection of OH-groups in the presence of phosphines have been explored. Rate acceleration in the Baylis - Hillman reaction was observed when a hydroxyl phosphine was used as the catalyst. Rhodium complexes with chiral bisphospholanes are highly enantioselective catalysts for the asymmetric hydrogenation of various kinds of functionalized olefins such as dehydroamino acid derivatives, itaconic acid derivatives, and enamides. An interesting feature of the hydroxyl phospholane system is that hydrogenation of some substrates can be carried out in water with >99% ee and 100% conversion (e.g., itaconic acid).

New C2 symmetric bis-aziridines efficient synthesis of (2S,5S)-1,6-di(p-toluenesulfonyloxy)-2,5-hexanediol, and (2S,3E,5S)-1,6-di(p-toluenesulfonyloxy)-2,5-hexenediol

The regioselective tosylation and functionalization of (S,S)-1,2,5,6-hexanetetrol is reported. The reductive aminocyclization of conformationally flexible diazidodiols by PPh3 leads to C2 symmetric bis-aziridines and to substituted furans.

2,5-Disubstituted Pyrrolidines from D-Mannitol-Derived Bis-Aziridines

Concise synthesesof 3,4-dihydroxy-2,5-disubstituted pyrrolidines have been achieved starting from D-mannitol-derived flexible L-Ido bis-aziridines.Nucleophilic ring opening of the N-Boc and N-Cbz activated bis-aziridines by phenylthiolate and azide ions h